Exp181

=Objective= To synthesize 66 Ugi adducts using Ugi 4CR following Explan005 .The target compound were ranked 55 -124 (except 58) in the [|DEXP014-V2B]   file from D-EXP014. The purpose of this experiment is to synthesize an anti-malarial compound based on the inhibition of falcipain-2, as described in this [|summary post]. =Procedure= To sixty nine vials, labeled 181# (55-124 except 58) and charged with methanol, four reactants [aldehyde, amine, acid and isocyanide] (0.5mmol each) were added to each in that order. After each addition, the resulting solution was vortexed for 30seconds (or more). The vials were capped tight and left at room temperature. The vials which formed solid precipitates or crystals were decanted and the solid was washed with methanol (3x 500uL) and dried under vacuum to obtain corresponding Ugi products.

(0.5mmol-103.1mg) || 5-Methylfurfurylamine (0.5mmol-55.7uL) || 2,6-dihydroxybenzoic aicd (0.5mmol-77.0mg) || n-butylisocyanide (0.5mmol-53uL) || **N** || (0.5mmol-103.1mg) || Furfurylamine (0.5mmol-44.2uL) || 2,4,6-trihydroxybenzoic acid.H2O (0.5mmol-94mg) || n-butylisocyanide (0.5mmol-53uL) || Reactants Insoluble || (0.5mmol-53.3uL) || Methylamine (0.5mmol-250uL) || Phenylpropynoic acid (0.5mmol-73.0mg) || TOSMIC (0.5mmol-97.6mg) || **N** || (0.5mmol-57.8uL) || Methylamine (0.5mmol-250uL) || 4-hydroxybenzoic acid (0.5mmol-69mg) || TOSMIC (0.5mmol-97.6mg) || **N** || (0.5mmol-53.3uL) || Furfurylamine (0.5mmol-44.2uL) || Phenylpropynoic acid (0.5mmol-73.0mg) || TOSMIC (0.5mmol-97.6mg) || **N** || (0.5mmol-73.8uL)  // || //3-Chloroaniline (0.5mmol-53uL) // || //alpha-hydroxyphenylacetic acid (0.5mmol-76mg) // || //TOSMIC (0.5mmol-97.6mg) // || N/A || (0.5mmol-83.1mg) || Methylamine (0.5mmol-250uL) || 4-hydroxybenzoic acid (0.5mmol-69mg) || TOSMIC (0.5mmol-97.6mg) || **N** || (0.5mmol-53.3uL) || Propylamine (0.5mmol-41.1uL) || 3,4-dihydroxyphenylaceticacid (0.5mmol-84.0mg) || TOSMIC (0.5mmol-97.6mg) || **N** || (0.5mmol-69.06mgl) || 1-hexylamine (0.5mmol-66ul) || 3-Methyl-2-butenoic acid (0.5mmol-50.0mg) || TOSMIC (0.5mmol-97.6mg) || **N** || (0.5mmol-83.1mg) || Benzylamine (0.5mmol-54.6uL) || Quinic Acid (0.5mmol-96.1mg) || t-butylisocyanide (0.5mmol-57.5uL) || **N** || (0.5mmol-61.0mg) || Methylamine (0.5mmol-250uL) || 2,4,6-trihydroxybenzoic acid.H2O (0.5mmol-94mg) || TOSMIC (0.5mmol-97.6mg) || **N** || (0.5mmol-61mg) || Furfurylamine (0.5mmol-44.2uL) || 3,4-dihydroxyphenylaceticacid (0.5mmol-84.0mg) || TOSMIC (0.5mmol-97.6mg) || **N** || (0.5mmol-76.0mg) || Methylamine (0.5mmol-250uL) || 3,4-dihydroxyphenylaceticacid (0.5mmol-84.0mg) || TOSMIC (0.5mmol-97.6mg) || **N** || (0.5mmol- 78.1mg) || Aniline (0.5mmol-45.5uL) || 2,4,6-trihydroxybenzoic acid.H2O (0.5mmol-94mg) || TOSMIC (0.5mmol-97.6mg) || Reactants Insoluble || (0.5mmol-57.8uL) || 3-Chloroaniline (0.5mmol-53uL) || 1-Pyrenebutyric acid (0.5mmol-144.1mg) || n-butylisocyanide (0.5mmol-53uL) || Reactants Insoluble || (0.5mmol-50.8uL) || Benzylamine (0.5mmol-54.6uL) || alpha-hydroxyphenylacetic acid (0.5mmol-76mg) || TOSMIC (0.5mmol-97.6mg) || **Y **No Ugi product || (0.5mmol-68.3uL) || Methylamine (0.5mmol-250uL) || 2,6-dihydroxybenzoic aicd.H2O (0.5mmol-77.0mg) || TOSMIC (0.5mmol-97.6mg) || **N** || (0.5mmol-50.8uL) || Methylamine (0.5mmol-250uL) || Boc-Trp-OH (0.5mmol-152.1mg) || t-butylisocyanide (0.5mmol-57.5uL) || **N** || (0.5mmol-69.06mgl) || Aniline (0.5mmol-45.5uL) || 3,4-dihydroxyphenylaceticacid (0.5mmol-84.0mg) || t-butylisocyanide (0.5mmol-57.5uL) || **N** || (0.5mmol-103.1mg) || Furfurylamine (0.5mmol-44.2uL) || alpha-hydroxyphenylacetic acid (0.5mmol-76mg) || n-butylisocyanide (0.5mmol-53uL) || **N** || (0.5mmol-69.06mgl) || Propylamine (0.5mmol-41.1uL) || diphenylaceitc acid (0.5mmol-106.1mg) || n-butylisocyanide (0.5mmol-53uL) || **N** || (0.5mmol-61uL) || 5-Methylfurfurylamine (0.5mmol-55.7uL) || 2,4,6-trihydroxybenzoic acid.H2O (0.5mmol-94mg) || n-butylisocyanide (0.5mmol-53uL) || Reactants Insoluble || (0.5mmol-53.3uL) || 1-hexylamine (0.5mmol-66ul) || 1-Pyrenebutyric acid (0.5mmol-144.1mg) || t-butylisocyanide (0.5mmol-57.5uL) || Reactants Insoluble || (0.5mmol-103.1mg) || Furfurylamine (0.5mmol-44.2uL) || 2,4,6-trihydroxybenzoic acid (0.5mmol-94mg) || t-butylisocyanide (0.5mmol-57.5uL) || Reactants Insoluble || (0.5mmol-61uL) || Aniline (0.5mmol-45.5uL) || 2,4,6-trihydroxybenzoic acid (0.5mmol-94mg) || TOSMIC (0.5mmol-97.6mg) || **Y ** || (0.5mmol- 78.1mg) || 2-Chloroaniline (0.5mmol-52.6uL) || 3,4-dihydroxyphenylaceticacid (0.5mmol-84.0mg) || t-butylisocyanide (0.5mmol-57.5uL) || Reactants Insoluble || (0.5mmol-69.06mgl) || Furfurylamine (0.5mmol-44.2uL) || 3,4-dihydroxyphenylaceticacid (0.5mmol-84.0mg) || TOSMIC (0.5mmol-97.6mg) || **N** || (0.5mmol-50.8uL) || Aniline (0.5mmol-45.5uL) || 1-Pyrenebutyric acid (0.5mmol-144.1mg) || n-butylisocyanide (0.5mmol-53uL) || Reactants Insoluble || (0.5mmol-61uL) || Benzylamine (0.5mmol-54.6uL) || alpha-hydroxyphenylacetic acid (0.5mmol-76mg) || n-butylisocyanide (0.5mmol-53uL) || **N** || (0.5mmol-53.3uL) || 3-Chloroaniline (0.5mmol-53uL) || 2,5-dimethoxyphenylacetic acid (0.5mmol-98.1) || TOSMIC (0.5mmol-97.6mg) || **N** || (0.5mmol-61.0mg) || Methylamine (0.5mmol-250uL) || 4-hydroxybenzoic acid (0.5mmol-69mg) || TOSMIC (0.5mmol-97.6mg) || **N** || (0.5mmol-69.7uL) || Methylamine (0.5mmol-250uL) || 1-Pyrenebutyric acid (0.5mmol-144.1mg) || t-butylisocyanide (0.5mmol-57.5uL) || Reactants Insoluble || (0.5mmol-69.06mgl) || 5-Methylfurfurylamine (0.5mmol-55.7uL) || diphenylaceitc acid (0.5mmol-106.1mg) || n-butylisocyanide (0.5mmol-53uL) || **N** || (0.5mmol-53.3uL) || 3-Chloroaniline (0.5mmol-53uL) || hexanoic acid (0.5mmol-62.6uL) || TOSMIC (0.5mmol-97.6mg) || Reactants Insoluble || (0.5mmol-69.06mgl) || Methylamine (0.5mmol-250uL) || 4-Nitrobenzoic acid (0.5mmol-83.5mg) || TOSMIC (0.5mmol-97.6mg) || Reactants Insoluble || (05.mmol-77.3mg) || Methylamine (0.5mmol-250uL) || Boc-Trp-OH (0.5mmol-152.1mg) || n-butylisocyanide (0.5mmol-53uL) || N/A || (0.5mmol-61uL) || 2-Chloroaniline (0.5mmol-52.6uL) || Decanoic acid (0.5mmol-96.5uL) || TOSMIC (0.5mmol-97.6mg) || **N** || (0.5mmol-53.3uL) || Aniline (0.5mmol-45.5uL) || hexanoic acid (0.5mmol-62.6uL) || TOSMIC (0.5mmol-97.6mg) || **N** || (0.5mmol-83.1mg) || Furfurylamine (0.5mmol-44.2uL) || 3,4-dihydroxyphenylaceticacid (0.5mmol-84.0mg) || TOSMIC (0.5mmol-97.6mg) || **N** || (05.mmol-77.3mg) || 3-Chloroaniline (0.5mmol-53uL) || alpha-hydroxyphenylacetic acid (0.5mmol-76mg) || TOSMIC (0.5mmol-97.6mg) || N/A || (0.5mmol-61uL) || Methylamine (0.5mmol-250uL) || 4-hydroxybenzoic acid (0.5mmol-69mg) || TOSMIC (0.5mmol-97.6mg) || **N** || (0.5mmol-53.3uL) || Furfurylamine (0.5mmol-44.2uL) || 3,4-dihydroxyphenylaceticacid (0.5mmol-84.0mg) || TOSMIC (0.5mmol-97.6mg) || **N** || (0.5mmol-61mg) || Methylamine (0.5mmol-250uL) || 2,3-dihydroxybenzoic acid. (0.5mmol-77.0mg) || TOSMIC (0.5mmol-97.6mg) || **N** || (0.5mmol-60.8uL) || 2-Chloroaniline (0.5mmol-52.6uL) || 4-hydroxybenzoic acid (0.5mmol-69mg) || TOSMIC (0.5mmol-97.6mg) || **N** || (0.5mmol-70.3mg) || Methylamine (0.5mmol-250uL) || Quinic Acid (0.5mmol-96.1mg) || TOSMIC (0.5mmol-97.6mg) || **N** || (0.5mmol-108.1mg) || Methylamine (0.5mmol-250uL) || 2,4,6-trihydroxybenzoic acid.H2O (0.5mmol-94mg) || TOSMIC (0.5mmol-97.6mg) || Reactants Insoluble || (0.5mmol-61.0mg) || 5-Methylfurfurylamine (0.5mmol-55.7uL) || 3,4-dihydroxyphenylaceticacid (0.5mmol-84.0mg) || TOSMIC (0.5mmol-97.6mg) || **N** || (0.5mmol-103.1mg) || Methylamine (0.5mmol-250uL) || alpha-hydroxyphenylacetic acid (0.5mmol-76mg) || n-butylisocyanide (0.5mmol-53uL) || **N** || (0.5mmol-74.6mg) || Methylamine (0.5mmol-250uL) || Quinic Acid (0.5mmol-96.1mg) || TOSMIC (0.5mmol-97.6mg) || **N** || (0.5mmol-69.06mgl) || t-butylamine (05mmol-52.5uL) || 4-chlorophenylacetic acid (0.5mmol-85.3mg) || TOSMIC (0.5mmol-97.6mg) || **N** || (0.5mmol- 78.1mg) || Methylamine (0.5mmol-250uL) || 4-hydroxybenzoic acid (0.5mmol-69mg) || TOSMIC (0.5mmol-97.6mg) || **N** || (0.5mmol-53.3uL) || Aniline (0.5mmol-45.5uL) || Phenylpropynoic acid (0.5mmol-73.0mg) || TOSMIC (0.5mmol-97.6mg) || **N** || (0.5mmol- 78.1mg) || Methylamine (0.5mmol-250uL) || Quinic Acid (0.5mmol-96.1mg) || TOSMIC (0.5mmol-97.6mg) || **<span style="COLOR: rgb(218,47,47)">Y **No Ugi product || (0.5mmol-61uL) || 1-hexylamine (0.5mmol-66ul) || 4-hydroxybenzoic acid (0.5mmol-69mg) || TOSMIC (0.5mmol-97.6mg) || **N** || (0.5mmol-53.3uL) || Aniline (0.5mmol-45.5uL) || 3,4-dihydroxyphenylaceticacid (0.5mmol-84.0mg) || TOSMIC (0.5mmol-97.6mg) || **N** || (0.5mmol-103.1mg) || Methylamine (0.5mmol-250uL) || 2,4,6-trihydroxybenzoic acid.H2O (0.5mmol-94mg) || t-butylisocyanide (0.5mmol-57.5uL) || Reactants Insoluble || (0.5mmol-60.8uL) || Methylamine (0.5mmol-250uL) || 2,3-dihydroxybenzoic acid (0.5mmol-77.0mg) || TOSMIC (0.5mmol-97.6mg) || **N** || (0.5mmol-83.1mg) || 3-Chloroaniline (0.5mmol-53uL) || 3,4-dihydroxyphenylaceticacid (0.5mmol-84.0mg) || TOSMIC (0.5mmol-97.6mg) || **N** || (0.5mmol-103.1mg) || 5-Methylfurfurylamine (0.5mmol-55.7uL) || 2,4,6-trihydroxybenzoic acid.H2O (0.5mmol-94mg) || n-butylisocyanide (0.5mmol-53uL) || Reactants Insoluble || (0.5mmol- 78.1mg) || 3-Chloroaniline (0.5mmol-53uL) || 3,4-dihydroxyphenylaceticacid (0.5mmol-84.0mg) || t-butylisocyanide (0.5mmol-57.5uL) || Reactants Insoluble || (0.5mmol-70.3mg) || Methylamine (0.5mmol-250uL) || 2,3-dihydroxybenzoic acid (0.5mmol-77.0mg) || TOSMIC (0.5mmol-97.6mg) || **N** || (0.5mmol-83.1mg) || Furfurylamine (0.5mmol-44.2uL) || 2,4,6-trihydroxybenzoic acid.H2O (0.5mmol-94mg) || TOSMIC (0.5mmol-97.6mg) || Reactants Insoluble || (0.5mmol-250uL) || 3,4-dihydroxyphenylaceticacid (0.5mmol-84.0mg) || TOSMIC (0.5mmol-97.6mg) || **N** || (0.5mmol-69.06mgl) || Methylamine (0.5mmol-250uL) || diphenylaceitc acid (0.5mmol-106.1mg) || n-butylisocyanide (0.5mmol-53uL) || **N** || (0.5mmol-121.0mg-??) || Methylamine (0.5mmol-250uL) || 2,4,6-trihydroxybenzoic acid.H2O (0.5mmol-94mg) || TOSMIC (0.5mmol-97.6mg) || **N** || (0.5mmol-69.06mgl) || 3-Chloroaniline (0.5mmol-53uL) || 4-chlorophenylacetic acid (0.5mmol-85.3mg) || TOSMIC (0.5mmol-97.6mg) || **N** || (0.5mmol-83.1mg) || 2-Chloroaniline (0.5mmol-52.6uL) || 4-hydroxybenzoic acid (0.5mmol-69mg) || TOSMIC (0.5mmol-97.6mg) || **N** || (0.5mmol-103.1mg) || Furfurylamine (0.5mmol-44.2uL) || 3,4-dihydroxyphenylaceticacid (0.5mmol-84.0mg) || TOSMIC (0.5mmol-97.6mg) || **N** || (0.5mmol-53.3uL) || Benzylamine (0.5mmol-54.6uL) || 3-(4-Methoxyphenyl)propionic acid (0.5mmol-90.1mg || TOSMIC (0.5mmol-97.6mg) || **N** || =Results= Insoluble || Insoluble || Insoluble || Day 1 || Day 3 || Day 12 || Amount: 46mg Yield: M.P : 169-171C IR [|HNMR] [|CNMR] [|FAB-MS] || Insoluble || Insoluble || Insoluble || CNMR IR FAB-MS Crystal Structure || Insoluble || Insoluble || Insoluble || Insoluble || Insoluble || Insoluble || Day 1 || Day 3 || Day 12 || Amount: 16mg - Isoluble in DMSO-D6 Yield M.P: 203-205C IR [|FAB-MS] || Insoluble || Insoluble || Insoluble || Insoluble ||
 * Exp-Lib Rank || Aldehyde || Amine || Acid || Isocyanide || Ppt (Y/N) & Yield ||
 * 181-55 || Phenanthrene-9-carboxaldehyde
 * 181-56 || Phenanthrene-9-carboxaldehyde
 * 181-57 || Salicylaldehyde
 * 181-59 || o-tolualdehyde
 * 181-60 || Salicylaldehyde
 * <span style="COLOR: rgb(240,15,15)">//<span style="COLOR: rgb(17,14,14); BACKGROUND-COLOR: rgb(228,7,7)"><span style="BACKGROUND-COLOR: rgb(255,255,255)">181-61 // || <span style="COLOR: rgb(240,15,15)">//<span style="COLOR: rgb(17,14,14); BACKGROUND-COLOR: rgb(228,7,7)"><span style="BACKGROUND-COLOR: rgb(255,255,255)"><span style="BACKGROUND-COLOR: rgb(255,255,255)"><span style="COLOR: rgb(207,7,7)"><span style="COLOR: rgb(235,10,10)">2,4,6-trimethylbenzaldehyde  -(spoilt)
 * 181-62 || 3,5-dimethoxybenzaldehyde
 * 181-63 || Salicylaldehyde
 * 181-64 || 3,4-dihydroxybenzaldehyde
 * 181-65 || 3,5-dimethoxybenzaldehyde
 * 181-66 || 3-hydroxybenzaldehyde
 * 181-67 || 4-hydroxybenzaldehyde
 * 181-68 || o-vanillin
 * 181-69 || 2-naphthaldehyde
 * 181-70 || o-tolualdehyde
 * 181-71 || Benzaldehyde
 * 181-72 || 4-(trifluoromethyl)benzaldehyde
 * 181-73 || Benzaldehdye
 * 181-74 || 3,4-dihydroxybenzaldehyde
 * 181-75 || Phenanthrene-9-carboxaldehyde
 * 181-76 || 3,4-dihydroxybenzaldehyde
 * 181-77 || 3-methoxybenzaldehyde
 * 181-78 || Salicylaldehyde
 * 181-79 || Phenanthrene-9-carboxaldehyde
 * 181-80 || 3-methoxybenzaldehyde
 * 181-81 || 2-naphthaldehyde
 * 181-82 || 3,4-dihydroxybenzaldehyde
 * 181-83 || Benzaldehye
 * 181-84 || 3-methoxybenzaldehyde
 * 181-85 || Salicylaldehyde
 * 181-86 || 3-hydroxybenzaldehyde
 * 181-87 || 2,4-dimethylbenzaldehyde
 * 181-88 || 3,4-dihydroxybenzaldehyde
 * 181-89 || Salicylaldehyde
 * 181-90 || 3,4-dihydroxybenzaldehyde
 * 181-91 || <span style="COLOR: rgb(196,23,23)">2-chloro-6-methylbenzaldehyde <span style="COLOR: rgb(240,15,15)">//<span style="COLOR: rgb(17,14,14); BACKGROUND-COLOR: rgb(228,7,7)"><span style="BACKGROUND-COLOR: rgb(255,255,255)"><span style="BACKGROUND-COLOR: rgb(255,255,255)">-(unavailable)  //
 * 181-92 || 3-methoxybenzaldehyde
 * 181-93 || Salicylaldehyde
 * 181-94 || 3,5-dimethoxybenzaldehyde
 * 181-95 || <span style="COLOR: rgb(210,15,15)">2-chloro-6-methylbenzaldehyde <span style="COLOR: rgb(240,15,15)">//<span style="COLOR: rgb(17,14,14); BACKGROUND-COLOR: rgb(228,7,7)"><span style="BACKGROUND-COLOR: rgb(255,255,255)"><span style="BACKGROUND-COLOR: rgb(255,255,255)">-(unavailable)  //
 * 181-96 || 3-methoxybenzaldehyde
 * 181-97 || Salicylaldehyde
 * 181-98 || 4-hydroxybenzaldehyde
 * 181-99 || 4-methoxybenzaldehyde
 * 181-100 || 4-chlorobenzaldehyde
 * 181-101 || 4,7-dimethoxy-1-naphthaldehyde
 * 181-102 || 3-hydroxybenzaldehyde
 * 181-103 || Phenanthrene-9-carboxaldehyde
 * 181-104 || 4-(Dimethylamino)benzaldehyde
 * 181-105 || 3,4-dihydroxybenzaldehyde
 * 181-106 || 2-naphthaldehyde
 * 181-107 || Salicylaldehyde
 * 181-108 || 2-naphthaldehyde
 * 181-109 || 3-methoxybenzaldehyde
 * 181-110 || Salicylaldehyde
 * 181-111 || Phenanthrene-9-carboxaldehyde
 * 181-112 || 4-methoxybenzaldehyde
 * 181-113 || Veratraldehyde
 * 181-114 || Phenanthrene-9-carboxaldehyde
 * 181-115 || 2-naphthaldehyde
 * 181-116 || 4-chlorobenzaldehyde
 * 181-117 || Veratraldehyde
 * 181-118 || 5-bromo-2-thiophenecarboxaldehyde (0.5mmol-59.4uL) || Methylamine
 * 181-119 || 3,4-dihydroxybenzaldehyde
 * 181-120 || 3,5-Bis(trifluoromethyl)benzaldehyde
 * 181-121 || 3,4-dihydroxybenzaldehyde
 * 181-122 || Veratraldehyde
 * 181-123 || Phenanthrene-9-carboxaldehyde
 * 181-124 || Salicylaldehyde
 * Exp ID || Day1 || Day-3 || Final || Analytical data ||
 * 181-55 || [[image:181-55day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-55day1.JPG"]] || [[image:181-55day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-55day3.JPG"]] ||  ||   ||
 * 181-56 || [[image:181-56day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-56day1.JPG"]] || [[image:181-56day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-56day3.JPG"]] ||  || Reactants
 * 181-57 || [[image:181-57day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-57day1.JPG"]] || [[image:181-57day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-57day3.JPG"]] ||  ||   ||
 * 181-59 || [[image:181-59day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-59day1.JPG"]] || [[image:181-59day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-59day3.JPG"]] ||  ||   ||
 * 181-60 || [[image:181-60day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-60day1.JPG"]] || [[image:181-60day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-60day3.JPG"]] ||  ||   ||
 * 181-62 || [[image:181-62day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-62day1.JPG"]] || [[image:181-62day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-62day3.JPG"]] ||  ||   ||
 * 181-63 || [[image:181-63day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-63day1.JPG"]] || [[image:181-63day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-63day3.JPG"]] ||  ||   ||
 * 181-64 || [[image:181-64day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-64day1.JPG"]] || [[image:181-64day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-64day3.JPG"]] ||  ||   ||
 * 181-65 || [[image:181-65day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-65day1.JPG"]] || [[image:181-65day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-65day3.JPG"]] ||  ||   ||
 * 181-66 || [[image:181-66day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-66day1.JPG"]] || [[image:181-66day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-66day3.JPG"]] ||  ||   ||
 * 181-67 || [[image:181-67day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-67day1.JPG"]] || [[image:181-67day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-67day3.JPG"]] ||  ||   ||
 * 181-68 || [[image:181-68day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-68day1.JPG"]] || [[image:181-68day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-68day3.JPG"]] ||  ||   ||
 * 181-69 || [[image:181-69day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-69day1.JPG"]] || [[image:181-69day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-69day3.JPG"]] ||  || Reactants
 * 181-70 || [[image:181-70day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-70day1.JPG"]] || [[image:181-70day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-70day3.JPG"]] ||  || Reactants
 * [|181-71] || [[image:181-71day1.JPG width="50" height="50"]]
 * 181-72 || [[image:181-72day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-72day1.JPG"]] || [[image:181-72day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-72day3.JPG"]] ||  ||   ||
 * 181-73 || [[image:181-73day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-73day1.JPG"]] || [[image:181-73day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-73day3.JPG"]] ||  ||   ||
 * 181-74 || [[image:181-74day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-74day1.JPG"]] || [[image:181-74day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-74day3.JPG"]] ||  ||   ||
 * 181-75 || [[image:181-75day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-75day1.JPG"]] || [[image:181-75day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-75day3.JPG"]] ||  ||   ||
 * 181-76 || [[image:181-76day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-76day1.JPG"]] || [[image:181-76day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-76day3.JPG"]] ||  ||   ||
 * 181-77 || [[image:181-77day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-77day1.JPG"]] || [[image:181-77day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-77day3.JPG"]] ||  || Reactants
 * 181-78 || [[image:181-78day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-78day1.JPG"]] || [[image:181-78day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-78day3.JPG"]] ||  || Reactants
 * 181-79 || [[image:181-79day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-79day1.JPG"]] || [[image:181-79day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-79day3.JPG"]] ||  || Reactants
 * 181-80 || [[image:181-80day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-80day1.JPG"]] || [[image:181-80day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-80day3.JPG"]] ||  || HNMR
 * 181-81 || [[image:181-81day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-81day1.JPG"]] || [[image:181-81day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-81day3.JPG"]] ||  || Reactants
 * 181-82 || [[image:181-82day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-82day1.JPG"]] || [[image:181-82day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-82day3.JPG"]] ||  ||   ||
 * 181-83 || [[image:181-83day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-83day1.JPG"]] || [[image:181-83day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-83day3.JPG"]] ||  || Reactants
 * 181-84 || [[image:181-84day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-84day1.JPG"]] || [[image:181-84day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-84day3.JPG"]] ||  ||   ||
 * 181-85 || [[image:181-85day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-85day1.JPG"]] || [[image:181-85day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-85day3.JPG"]] ||  ||   ||
 * 181-86 || [[image:181-86day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-86day1.JPG"]] || [[image:181-86day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-86day3.JPG"]] ||  ||   ||
 * 181-87 || [[image:181-87day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-87day1.JPG"]] || [[image:181-87day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-87day3.JPG"]] ||  || Reactants
 * 181-88 || [[image:181-88day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-88day1.JPG"]] || [[image:181-88day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-88day3.JPG"]] ||  ||   ||
 * 181-89 || [[image:181-89day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-89day1.JPG"]] || [[image:181-89day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-89day3.JPG"]] ||  ||   ||
 * 181-90 || [[image:181-90day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-90day1.JPG"]] || [[image:181-90day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-90day3.JPG"]] ||  || Reactants
 * 181-92 || [[image:181-92day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-92day1.JPG"]] || [[image:181-92day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-92day3.JPG"]] ||  ||   ||
 * 181-93 || [[image:181-93day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-93day1.JPG"]] || [[image:181-93day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-93day3.JPG"]] ||  ||   ||
 * 181-94 || [[image:181-94day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-94day1.JPG"]] || [[image:181-94day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-94day3.JPG"]] ||  ||   ||
 * 181-96 || [[image:181-96day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-96day1.JPG"]] || [[image:181-96day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-96day3.JPG"]] ||  ||   ||
 * 181-97 || [[image:181-97day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-97day1.JPG"]] || [[image:181-97day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-97day3.JPG"]] ||  ||   ||
 * 181-98 || [[image:181-98day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-98day1.JPG"]] || [[image:181-98day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-98day3.JPG"]] ||  ||   ||
 * 181-99 || [[image:181-99day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-99day1.JPG"]] || [[image:181-99day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-99day3.JPG"]] ||  ||   ||
 * 181-100 || [[image:181-100day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-100day1.JPG"]] || [[image:181-100day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-100day3.JPG"]] ||  || Reactants
 * 181-101 || [[image:181-101day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-101day1.JPG"]] || [[image:181-101day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-101day3.JPG"]] ||  || Reactants
 * 181-102 || [[image:181-102day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-102day1.JPG"]] || [[image:181-102day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-102day3.JPG"]] ||  ||   ||
 * 181-103 || [[image:181-103day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-103day1.JPG"]] || [[image:181-103day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-103day3.JPG"]] ||  ||   ||
 * 181-104 || [[image:181-104day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-104day1.JPG"]] || [[image:181-104day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-104day3.JPG"]] ||  ||   ||
 * 181-105 || [[image:181-105day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-105day1.JPG"]] || [[image:181-105day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-105day3.JPG"]] ||  ||   ||
 * 181-106 || [[image:181-106day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-106day1.JPG"]] || [[image:181-106day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-106day3.JPG"]] ||  ||   ||
 * 181-107 || [[image:181-107day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-107day1.JPG"]] || [[image:181-107day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-107day3.JPG"]] ||  ||   ||
 * [|181-108] || [[image:181-108day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-108day1.JPG"]]
 * 181-109 || [[image:181-109day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-109day1.JPG"]] || [[image:181-109day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-109day3.JPG"]] ||  ||   ||
 * 181-110 || [[image:181-110day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-110day1.JPG"]] || [[image:181-110day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-110day3.JPG"]] ||  ||   ||
 * 181-111 || [[image:181-111day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-111day1.JPG"]] || [[image:181-111day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-111day3.JPG"]] ||  || Reactants
 * 181-112 || [[image:181-112day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-112day1.JPG"]] || [[image:181-112day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-112day3.JPG"]] ||  ||   ||
 * 181-113 || [[image:181-113day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-113day1.JPG"]] || [[image:181-113day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-113day3.JPG"]] ||  ||   ||
 * 181-114 || [[image:181-114day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-114day1.JPG"]] || [[image:181-114day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-114day3.JPG"]] ||  || Reactants
 * 181-115 || [[image:181-115day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-115day1.JPG"]] || [[image:181-115day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-115day3.JPG"]] ||  || Reactants
 * 181-116 || [[image:181-116day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-116day1.JPG"]] || [[image:181-116day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-116day3.JPG"]] ||  ||   ||
 * 181-117 || [[image:181-117day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-117day1.JPG"]] || [[image:181-117day3.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-117day3.JPG"]] ||  || Reactants
 * 181-118 || [[image:181-118day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-118day3.JPG"]] || [[image:181-118day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-118day3.JPG"]] ||  ||   ||
 * 181-119 || [[image:181-119day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-119day3.JPG"]] || [[image:181-119day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-119day3.JPG"]] ||  ||   ||
 * 181-120 || [[image:181-120day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-120day3.JPG"]] || [[image:181-120day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-120day3.JPG"]] ||  ||   ||
 * 181-121 || [[image:181-121day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-121day3.JPG"]] || [[image:181-121day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-121day3.JPG"]] ||  ||   ||
 * 181-122 || [[image:181-122day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-122day3.JPG"]] || [[image:181-122day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-122day3.JPG"]] ||  ||   ||
 * 181-123 || [[image:181-123day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-123day3.JPG"]] || [[image:181-123day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-123day3.JPG"]] ||  ||   ||
 * 181-124 || [[image:181-124day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-124day3.JPG"]] || [[image:181-124day1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/181-124day3.JPG"]] ||  ||   ||

=Discussion= 181-71 From the HNMR of the sample it is obvious that the solid obtained is not a clean ugi product, if at all. Similarly 181-108, the FAB MS shows no peaks corresponding to a ugi product. It is beyond the scope of this project to isolate or determine the nautre of these compounds.

=Conclusions= No Ugi products isolated from this experiment. =Log= 13:00 Made up a solution of each aldehyde in methanol in vials labelled with Exp-Rank number. 2ml of methanol was used in vials which did not use methyl amine (in methanol solution). Vials which used methyl amine as the amine component used only 1850uL of methanol. Each vial was vortexed for 30s. Phenanthrene-9-Carboxaldehyde (181-55,56,75,79,103,111,114,123) and 4,7-dimethoxy-1-naphthaldehyde (181-101) did not go in solution. Weights of dry,empty vials with labels and no cap- 181-055- 4.7012g 181-056- 4.6561g 181-057- 4.6500g 181-059- 4.6503g 181-060- 4.6620g 181-061- 4.6585g 181-062- 4.6755g 181-063- 4.7131g 181-064- 4.7336g 181-065- 4.6360g 181-066- 4.6888g 181-067- 4.6888g 181-068- 4.6744g 181-069- 4.6813g 181-070- 4.6575g 181-071- 4.6683g 181-072- 4.6789g 181-073- 4.6613g 181-074- 4.6420g 181-075- 4.6650g 181-076- 4.6905g 181-077- 4.6530g 181-078- 4.6733g 181-079- 4.6621g 181-080- 4.6685g 181-081- 4.6540g 181-082- 4.6532g 181-083- 4.6900g 181-084- 4.6943g 181-085- 4.6545g 181-086- 4.6466g 181-087- 4.6879g 181-088- 4.6700g 181-089- 4.6788g 181-090- 4.6638g 181-092- 4.6990g 181-093- 4.6676g 181-094- 4.6493g 181-096- 4.6820g 181-097- 4.6760g 181-098- 4.6610g 181-099- 4.6677g 181-100- 4.6600g 181-101- 4.6686g 181-102- 4.6785g 181-103- 4.6673g 181-104- 4.6729g 181-105- 4.6545g 181-106- 4.6545g 181-107- 4.6795g 181-108- 4.6786g 181-109- 4.6900g 181-110- 4.6700g 181-111- 4.6675g 181-112- 4.6415g 181-113- 4.6558g 181-114- 4.6785g 181-115- 4.6902g 181-116- 4.6684g 181-117- 4.6600g 181-118- 4.6712g 181-119- 4.6530g 181-120- 4.6618g 181-121- 4.6700g 181-122- 4.6655g 181-123- 4.6560g 181-124- 4.6948g 15:30 Added respective amines to each vial. Vortexed for 30s. 23:00 Completed addition of respective acids to each vial. The vials were vortexed for 30s each after the acid addition. 22:30 Completed addition of respective isocyanides to each vial. The vials were vortexed for 30s each after the isocyanide addition; obtained picture of the vials -(**Day-1 series**) 16:50 Obtained pictures of the vials-(**Day-3 series**) 11:45 Vortexed vial containing solutions 181-055 -181-124 for 15s each. Solution number 181-100 previously reported as 'reactants insoluble' has now turned clear. 10:00 Observed solid in vials 181-71 and 181-108; obtained pictures. 14:00 Vortexed 181-71 and 181-108 for 30s each, centrifuged them for 1min and decanted the supernatant. The residue was washed with methanol (3x 1000uL) each time vortexing the solution for 30s and centrifuging for 1min before decanting the supernatant. 15:45 The residues from 181-71 and 181-108 were set on high vac. 18:45 Removed them from high vac and obtained the now renamed 181-71A (46 mg) and 181-108A (16 mg)
 * 2008-04-09**
 * 2008-04-10**
 * 2008-04-14**
 * 2008-04-16**
 * 2008-04-23**
 * 2008-04-25**
 * 2008-04-30**

Tags

 * Chemical || Inchi || Inchikey ||
 * [|benzaldehyde] || [|InChI=1/C7H6O/c8-6-7-4-2-1-3-5-7/h1-6H] || [|HUMNYLRZRPPJDN]-[|UHFFFAOYAE] ||
 * [|3-methoxybenzaldehyde] || [|InChI=1/C8H8O2/c1-10-8-4-2-3-7(5-8)6-9/h2-6H,1H3/i1-12,2-12,3-12,4-12,5-12,6-12,7-12,8-12,9-16,10-16] || [|WMPDAIZRQDCGFH]-[|UHFFFAOYAC] ||
 * [|Phenanthrene-9-carboxaldehyde] || [|InChI=1/C15H10O/c16-10-12-9-11-5-1-2-6-13(11)15-8-4-3-7-14(12)15/h1-10H] || [|QECIGCMPORCORE]-[|UHFFFAOYAE] ||
 * [|Salicylaldehyde] || [|InChI=1/C7H6O2/c8-5-6-3-1-2-4-7(6)9/h1-5,9H] || [|SMQUZDBALVYZAC]-[|UHFFFAOYAD] ||
 * [|3,4-dimethoxybenzaldehyde] || [|InChI=1/C9H10O3/c1-11-8-4-3-7(6-10)5-9(8)12-2/h3-6H,1-2H3] || [|WJUFSDZVCOTFON]-[|UHFFFAOYAT] ||
 * [|4-methylbenzaldehyde] || [|InChI=1/C8H8O/c1-7-2-4-8(6-9)5-3-7/h2-6H,1H3/i1-12,2-12,3-12,4-12,5-12,6-12,7-12,8-12,9-16] ||  ||
 * [|2-naphthaldehyde] || [|InChI=1/C11H8O/c12-8-9-5-6-10-3-1-2-4-11(10)7-9/h1-8H] || [|PJKVFARRVXDXAD]-[|UHFFFAOYAM] ||
 * [|2,3-dihydroxybenzaldehyde] || [|InChI=1/C7H6O3/c8-4-5-2-1-3-6(9)7(5)10/h1-4,9-10H] || [|IXWOUPGDGMCKGT]-[|UHFFFAOYAD] ||
 * [|4-chlorobenzaldehyde] || [|InChI=1/C7H5ClO/c8-7-3-1-6(5-9)2-4-7/h1-5H] || [|AVPYQKSLYISFPO]-[|UHFFFAOYAQ] ||
 * [|4-methoxybenzaldehyde] || [|InChI=1/C8H8O2/c1-10-8-4-2-7(6-9)3-5-8/h2-6H,1H3] || [|ZRSNZINYAWTAHE]-[|UHFFFAOYAA] ||
 * [|3,4-dihydroxybenzaldehyde] || [|nChI=1/C7H6O3/c8-4-5-1-2-6(9)7(10)3-5/h1-4,9-10H] || [|IBGBGRVKPALMCQ]-[|UHFFFAOYAN] ||
 * [|3-hydoxybenzaldehyde] || [|InChI=1/C7H6O2/c8-5-6-2-1-3-7(9)4-6/h1-5,9H] || [|IAVREABSGIHHMO]-[|UHFFFAOYAC] ||
 * [|3,5-dimethoxybenzaldehyde] || [|InChI=1/C9H10O3/c1-11-8-3-7(6-10)4-9(5-8)12-2/h3-6H,1-2H3] || [|VFZRZRDOXPRTSC]-[|UHFFFAOYAG] ||
 * [|4,7-Dimethoxy-1-naphthaldehyde] || [|InChI=1/C13H12O3/c1-15-10-4-5-11-12(7-10)9(8-14)3-6-13(11)16-2/h3-8H,1-2H3] || [|FFAODEUKHYBIKI]-[|UHFFFAOYAI] ||
 * [|5-methylfurfurylamine] || [|InChI=1/C6H9NO/c1-5-2-3-6(4-7)8-5/h2-3H,4,7H2,1H3] || [|YSEAGSCGERFGBL]-[|UHFFFAOYAH] ||
 * [|furfurylamine] || [|InChI=1/C5H7NO/c6-4-5-2-1-3-fu7-5/h1-3H,4,6H2c] || [|DDRPCXLAQZKBJP]-[|UHFFFAOYAX] ||
 * [|methylamine] || [|InChI=1/CH5N/c1-2/h2H2,1H3] || [|BAVYZALUXZFZLV]-[|UHFFFAOYAN] ||
 * [|n-propylamine] || [|InChI=1/C3H9N/c1-2-3-4/h2-4H2,1H3] || [|WGYKZJWCGVVSQN]-[|UHFFFAOYAG] ||
 * [|aniline] || [|InChI=1/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2] || [|PAYRUJLWNCNPSJ]-[|UHFFFAOYAP] ||
 * [|3-chloroaniline] || [|InChI=1/C6H6ClN/c7-5-2-1-3-6(8)4-5/h1-4H,8H2/i1-12,2-12,3-12,4-12,5-12,6-12,7-35,8-14] ||  ||
 * [|3,4-dihydroxyphenylacetiacid] || [|InChI=1/C8H8O4/c9-6-2-1-5(3-7(6)10)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)] || [|CFFZDZCDUFSOFZ]-[|UHFFFAOYAU] ||
 * [|5-nitrosalicylic acid] || [|InChI=1/C7H5NO5/c9-6-2-1-4(8(12)13)3-5(6)7(10)11/h1-3,9H,(H,10,11)] || [|PPDRLQLKHRZIJC]-[|UHFFFAOYAT] ||
 * [|benzoic acid] || [|InChI=1/C7H6O2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9)] || [|WPYMKLBDIGXBTP]-[|UHFFFAOYAD] ||
 * [|Boc-L-tryptophan] || [|InChI=1/C1 ​6H20N2O4/c​1-16(2,3)2​2-15(21)18​-13(14(19)​20)8-10-9-​17-12-7-5-​ 4-6-11(10)​12/h4-7,9,​13,17H,8H2​,1-3H3,(H,​18,21)(H,1​9,20)] || [|NFVNYBJCJGKVQK]-[|UHFFFAOYAR] ||
 * [|2,4,6-trihydroxybenzoicacid] || [|InChI=1/C7H6O5/c8-3-1-4(9)6(7(11)12)5(10)2-3/h1-2,8-10H,(H,11,12)] || [|IBHWREHFNDMRPR]-[|UHFFFAOYAP] ||
 * [|2-methylpropeneoicacid] || [|InChI=1/C4H6O2/c1-3(2)4(5)6/h1H2,2H3,(H,5,6)] || [|CERQOIWHTDAKMF]-[|UHFFFAOYAE] ||
 * [|(±)-2-Phenylbutanoic acid] || [|InChI=1/C10H12O2/c1-2-9(10(11)12)8-6-4-3-5-7-8/h3-7,9H,2H2,1H3,(H,11,12)] || [|OFJWFSNDPCAWDK]-[|UHFFFAOYAE] ||
 * [|D-(−)-Quinic acid] || [|InChI=1/C7H12O6/c8-3-1-7(13,6(11)12)2-4(9)5(3)10/h3-5,8-10,13H,1-2H2,(H,11,12)/t3-,4-,5?,7?/m1/s1] || [|AAWZDTNXLSGCEK]-[|LNVDRNJUBH] ||
 * [|n-butanoic acid] || [|InChI=1/C4H8O2/c1-2-3-4(5)6/h2-3H2,1H3,(H,5,6)] || [|FERIUCNNQQJTOY]-[|UHFFFAOYAP] ||
 * [|Mandelic acid] || [|InChI=1/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)/t7-/m0/s1] || [|IWYDHOAUDWTVEP]-[|ZETCQYMHBP] ||
 * [|2-Hydroxy-5-nitrobenzoicacid] || [|InChI=1/C7H5NO5/c9-6-2-1-4(8(12)13)3-5(6)7(10)11/h1-3,9H,(H,10,11)] || [|PPDRLQLKHRZIJC]-[|UHFFFAOYAT] ||
 * [|(2,5-Dimethoxyphenyl)acetic acid] || [|InChI=1/C10H12O4/c1-13-8-3-4-9(14-2)7(5-8)6-10(11)12/h3-5H,6H2,1-2H3,(H,11,12)] || [|BBZDYQUXRFATHZ]-[|UHFFFAOYAX] ||
 * [|TOSMIC] || [|InChI=1/C9H9NO2S/c1-8-3-5-9(6-4-8)13(11,12)7-10-2/h3-6H,7H2,1H3] || [|CFOAUYCPAUGDFF]-[|UHFFFAOYA] ||
 * [|n-butylisocyanide] || [|InChI=1/C5H9N/c1-3-4-5-6-2/h3-5H2,1H3] || [|FSBLVBBRXSCOKU]-[|UHFFFAOYAR] ||
 * [|t-butylisocyanide] || [|InChI=1/C5H9N/c1-5(2,3)6-4/h1-3H3] || [|FAGLEPBREOXSAC]-[|UHFFFAOYAL] ||
 * [|4-hydroxybenzoic acid] || [|InChI=1/C7H6O3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H,(H,9,10)] || [|FJKROLUGYXJWQN]-[|UHFFFAOYAQ] ||
 * [|2,5-dimethoxyphenylacetic acid] || [|InChI=1/C10H12O4/c1-13-8-3-4-9(14-2)7(5-8)6-10(11)12/h3-5H,6H2,1-2H3,(H,11,12)] || [|BBZDYQUXRFATHZ]-[|UHFFFAOYAX] ||
 * [|diphenylacetic acid] || [|InChI=1/C14H12O2/c15-14(16)13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10,13H,(H,15,16)] || [|PYHXGXCGESYPCW]-[|UHFFFAOYAC] ||
 * [|3-methylbut-2-enoic acid] || [|InChI=1/C5H8O2/c1-4(2)3-5(6)7/h3H,1-2H3,(H,6,7)] || [|YYPNJNDODFVZLE]-[|UHFFFAOYAX] ||
 * [|2,6-dihydroxybenzoic aicd] || [|InChI=1/C7H6O4/c8-4-2-1-3-5(9)6(4)7(10)11/h1-3,8-9H,(H,10,11)] || [|AKEUNCKRJATALU]-[|UHFFFAOYAG] ||
 * [|Phenylpropynoic acid] || [|InChI=1/C9H6O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5H,(H,10,11)] || [|XNERWVPQCYSMLC]-[|UHFFFAOYAX] ||
 * [|1-hexylamine] || [|InChI=1/C6H15N/c1-2-3-4-5-6-7/h2-7H2,1H3] || [|BMVXCPBXGZKUPN]-[|UHFFFAOYAQ] ||
 * [|Benzylamine] || [|InChI=1/C7H9N/c8-6-7-4-2-1-3-5-7/h1-5H,6,8H2] || [|WGQKYBSKWIADBV]-[|UHFFFAOYAL] ||
 * [|3-hydroxybenzaldehyde] || [|InChI=1/C7H6O2/c8-5-6-2-1-3-7(9)4-6/h1-5,9H] || [|IAVREABSGIHHMO]-[|UHFFFAOYAC] ||
 * [|2,4,6-trimethylbenzaldehyde] || [|InChI=1/C10H12O/c1-7-4-8(2)10(6-11)9(3)5-7/h4-6H,1-3H3/i1-12,2-12,3-12,4-12,5-12,6-12,7-12,8-12,9-12,1-12,11-16] ||  ||
 * [|2-methylbenzaldehyde] || [|InChI=1/C8H8O/c1-7-4-2-3-5-8(7)6-9/h2-6H,1H3/i1-12,2-12,3-12,4-12,5-12,6-12,7-12,8-12,9-16] ||  ||
 * [|2-Hydroxybenzaldehyde] || [|InChI=1/C7H6O2/c8-5-6-3-1-2-4-7(6)9/h1-5,9H] || [|SMQUZDBALVYZAC]-[|UHFFFAOYAD] ||