Exp174

=Objective= To synthesize 26 Ugi adducts using Ugi 4CR following Explan005. The target compounds were ranked [|31-54] (except 32,37 and 48, pyrene derivatives) 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 twentyone vials, labeled 174# (31-54 sans 32,37,48) 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 30s (or more). The vials were capped tight and left at room temperature. The vials which formed solid precipitates or crystals were decanted, the solid was washed with methanol (3x 500uL) and dried under vacuum to obtain corresponding Ugi products.

VB2Rank || Solvent || Aldehyde || Amine || Acid || Isocyanide || Ppt(Y/N) & Yield || -0.5mmol-50.8uL || 5-methylfurfurylamine -0.5mmol-55.7uL || 3,4-dihydroxyphenylacetic acid -0.5mmol-84.1mg || TOSMIC -0.5mmol-97.62mg || No Ppt || -0.5mmol-61uL || furfurylamine -0.5mmol-44.2uL || 3,4-dihydroxyphenylacetic acid -0.5mmol-84.1mg || TOSMIC -0.5mmol-97.62mg || No Ppt || -0.5mmol-103.12mg || methylamine (2M in methanol) -0.5mmol-250uL || 5-nitrosalicylic acid -0.5mmol-91.56mg || n-butylisocyanide -0.5mmol-52.3uL || **YES ** || -0.5mmol-53uL || furfurylamine -0.5mmol-44.2uL || benzoic acid -0.5mmol- 122.12mg || TOSMIC -0.5mmol-97.62mg || No Ppt || -0.5mmol-53uL || methylamine (2M in methanol) -0.5mmol-250uL || Boc-L-tryptophan -0.5mmol-152.17mg || n-butylisocyanide -0.5mmol-52.3uL || No Ppt || -0.5mmol-83.1mg || methylamine (2M in methanol) -0.5mmol-250uL || 3,4-dihydroxyphenylacetic acid -0.5mmol-84.1mg || TOSMIC -0.5mmol-97.62mg || No Ppt || -0.5mmol-59uL || n-propylamine -0.5mmol-41.1uL || 3,4-dihydroxyphenylacetic acid -0.5mmol-84.1mg || TOSMIC -0.5mmol-97.62mg || No Ppt || -0.5mmol-78.09mg || methylamine (2M in methanol) -0.5mmol-250uL || 2,4,6-trihydroxybenzoicacid.H2O -0.5mmol-94.1mg || TOSMIC -0.5mmol-97.62mg || No Ppt || -0.5mmol- 69.06mg || aniline -0.5mmol-45.5uL || 2-methylpropeneoicacid -0.5mmol-42.4uL || TOSMIC -0.5mmol-97.62mg || No Ppt || -0.5mmol-70.3mg || 5-methylfurfurylamine -0.5mmol-55.7uL || 3,4-dihydroxyphenylacetic acid -0.5mmol-84.1mg || TOSMIC -0.5mmol-97.62mg || No Ppt || -0.5mmol-103.12mg || 5-methylfurfurylamine -0.5mmol-55.7uL || 3,4-dihydroxyphenylacetic acid -0.5mmol-84.1mg || t-butylisocyanide -0.5mmol-56.5uL || **YES ** || -0.5mmol- 61uL || methylamine (2M in methanol) -0.5mmol-250uL || 2,4,6-trihydroxybenzoicacid.H2O -0.5mmol-94.1mg || TOSMIC -0.5mmol-97.62mg || No Ppt || -0.5mmol-69.06mg || 3-chloroaniline -0.5mmol-53uL || (±)-2-Phenylbutanoic acid -0.5mmol-82.1mg || TOSMIC -0.5mmol-97.62mg || No Ppt || -0.5mmol-61.06mg || methylamine (2M in methanol) -0.5mmol-250uL || Boc-L-tryptophan -0.5mmol-152.17mg || n-butylisocyanide -0.5mmol-52.3uL || No Ppt || -0.5mmol-83.1mg || 5-methylfurfurylamine -0.5mmol-55.7uL || D-(−)-Quinic acid -0.5mmol-96.1mg || t-butylisocyanide -0.5mmol-56.5uL || No Ppt || -0.5mmol-61uL || 5-methylfurfurylamine -0.5mmol-55.7uL || 3,4-dihydroxyphenylacetic acid -0.5mmol-84.1mg || TOSMIC -0.5mmol-97.62mg || No Ppt || -0.5mmol-53uL || 3-chloroaniline -0.5mmol-53uL || butyric acid -0.5mmol-45.7uL || TOSMIC -0.5mmol-97.62mg || No Ppt || -0.5mmol-53uL || 3-chloroaniline -0.5mmol-53uL || Mandelic acid -0.5mmol- 76.075mg || TOSMIC -0.5mmol-97.62mg || No Ppt || -0.5mmol-108.1mg || methylamine (2M in methanol) -0.5mmol-250uL || 5-nitrosalicylic acid -0.5mmol-91.56mg || n-butylisocyanide -0.5mmol-52.3uL || No Ppt || -0.5mmol-53uL || aniline -0.5mmol-45.5uL || (2,5-Dimethoxyphenyl)acetic acid -0.5mmol-98.1mg || TOSMIC -0.5mmol-97.62mg || No Ppt || -0.5mmol-61uL || furfurylamine -0.5mmol-44.2uL || 3,4-dihydroxyphenylacetic acid -0.5mmol-84.1mg || TOSMIC -0.5mmol-97.62mg || No Ppt ||
 * ExpID/
 * 174A/31 || Methanol || benzaldehyde
 * 174B/33 || Methanol || 3-methoxybenzaldehyde
 * 174C/34 || Methanol || Phenanthrene-9-carboxaldehyde
 * 174D/35 || Methanol || Salicylaldehyde
 * 174E/36 || Methanol || Salicylaldehyde
 * 174F/38 || Methanol || 3,4-dimethoxybenzaldehyde
 * 174G/39 || Methanol || 4-methylbenzaldehyde
 * 174H/40 || Methanol || 2-naphthaldehyde
 * 174I/41 || Methanol || 3,4-dihydroxybenzaldehyde
 * 174J/42 || Methanol || 4-chlorobenzaldehyde
 * 174K/43 || Methanol || Phenanthrene-9-carboxaldehyde
 * 174L/44 || Methanol || 4-methoxybenzaldehyde
 * 174M/45 || Methanol || 3,4-dihydroxybenzaldehyde
 * 174N/46 || Methanol || 3-hydroxybenzaldehyde
 * 174O/47 || Methanol || 3,5-dimethoxybenzaldehyde
 * 174P/49 || Methanol || 3-methoxybenzaldehyde
 * 174Q/50 || Methanol || Salicylaldehyde
 * 174R/51 || Methanol || Salicylaldehyde
 * 174S/52 || Methanol || 4,7-Dimethoxy-1-naphthaldehyde
 * 174T/53 || Methanol || Salicylaldehyde
 * 174U/54 || Methanol || 4-methoxybenzaldehyde

**Results**
 =**D**iscussion= From the proton NMR few peaks which may correspond to a ugi product are seen, but the chiral proton which was expected to appear between 5.5-6.0 ppm is missing. Also the FAB-MS rejects the idea of a ugi product. However CNMR shows all the 26 carbons which could correspond to a ugi product. Therefore in view of the ambiguity of the spectral results, a crystal analysis of the sample maybe useful. A lot of solvent has evaporated by day12 and so the experiment would have to be repeated making sure the vessel is tightly closed. =Conclusion= A Ugi product could not be isolated from the reactions performed. = = =**Log**=
 * ExpID || Day 1 || Day 2 || Day-12 || Characterization ||
 * 174A || [[image:174Aday1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/174Aday1.JPG"]] || [[image:174Aday2.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/174Aday2.JPG"]] || No Ppt ||  ||
 * 174B || [[image:174Bday1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/174Bday1.JPG"]] || [[image:174Bday2.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/174Bday2.JPG"]] || No Ppt ||  ||
 * [|174C] || [[image:174Cday1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/174Cday1.JPG"]] || [[image:174Cday2.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/174Cday2.JPG"]] || [[image:174Cday12.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/174Cday12.JPG"]] || Amount: 33 mg; Yield -
 * 1) Melting Point :171-173C
 * 2) [|IR]
 * 3) [|HNMR]
 * 4) [|HNMR] [H-Exchange with methanol-d4]
 * 5)   [|Overlay] [with labile H Vs Exchanged]
 * 6) [|CNMR]
 * 7) [|FAB-MS] ||
 * 174D || [[image:174Dday1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/174Dday1.JPG"]] || [[image:174Dday2.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/174Dday2.JPG"]] || No Ppt ||  ||
 * 174E || [[image:174Eday1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/174Eday1.JPG"]] || [[image:174Eday2.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/174Eday2.JPG"]] || No Ppt ||  ||
 * 174F || [[image:174Fday1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/174Fday1.JPG"]] || [[image:174Fday2.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/174Fday2.JPG"]] || No Ppt ||  ||
 * 174G || [[image:174Gday1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/174Gday1.JPG"]] || [[image:174Gday2.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/174Gday2.JPG"]] || No Ppt ||  ||
 * 174H || [[image:174Hday1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/174Hday1.JPG"]] || [[image:174Hday2.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/174Hday2.JPG"]] || No Ppt ||  ||
 * 174I || [[image:174Iday1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/174Iday1.JPG"]] || [[image:174Iday2.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/174Iday2.JPG"]] || No Ppt ||  ||
 * 174J || [[image:174Jday1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/174Jday1.JPG"]] || [[image:174Jday2.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/174Jday2.JPG"]] || No Ppt ||  ||
 * [|174K] || [[image:174Kday1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/174Kday1.JPG"]] || [[image:174Kday2.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/174Kday2.JPG"]] || [[image:174Kday12.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/174Kday12.JPG"]] || Amount: 27 mg; Yield -
 * 1) Melting Point : 143-145C
 * IR
 * 1)   [|HNMR]
 * 2) [|HNMR][H-Exchange with methanol-d4]
 * 3) <span class="wiki_link_ext">[|Overlay]  [with labile H Vs Exchanged]
 * 4) [|CNMR]
 * 5) [|FAB-MS] (Nominal Mass)
 * 6) [|FAB-MS] (HRMS) ||
 * 174L || [[image:174Lday1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/174Lday1.JPG"]] || [[image:174Lday2.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/174Lday2.JPG"]] || No Ppt ||  ||
 * 174M || [[image:174Mday1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/174Mday1.JPG"]] || [[image:174Mday2.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/174Mday2.JPG"]] || No Ppt ||  ||
 * 174N || [[image:174Nday1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/174Nday1.JPG"]] || [[image:174Nday2.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/17NAday2.JPG"]] || No Ppt ||  ||
 * 174O || [[image:174Oday1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/174Oday1.JPG"]] || [[image:174Oday2.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/174Oday2.JPG"]] || No Ppt ||  ||
 * 174P || [[image:174Pday1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/174Pday1.JPG"]] || [[image:174Pday2.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/174Pday2.JPG"]] || No Ppt ||  ||
 * 174Q || [[image:174Qday1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/174Qday1.JPG"]] || [[image:174Qday2.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/174Qday2.JPG"]] || No Ppt ||  ||
 * 174R || [[image:174Rday1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/174Rday1.JPG"]] || [[image:174Rday2.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/174Rday2.JPG"]] || No Ppt ||  ||
 * 174S || [[image:174Sday1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/174Sday1.JPG"]] || [[image:174Sday2.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/174Sday2.JPG"]] || No Ppt ||  ||
 * | 174T || [[image:174Tday1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/174Tday1.JPG"]] || [[image:174Tday2.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/174Tday2.JPG"]] || No Ppt ||  ||
 * 174U || [[image:174Uday1.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/174Uday1.JPG"]] || [[image:174Uday2.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/174Uday2.JPG"]] || No Ppt ||  ||
 * [|174C]
 * [|174K]

2008-04-02
14:50 Pipetted out methanol (2mL) in 14 one dram vials. Also pipetted out methanol (1850uL) in 7 other vials (these will accommodate 2.0 M methyl amine (250uL) as the amine component). The vials with 2ml methanol are labelled 174-A, B, D, G, I, J, K, M, O, P, Q, R, T, and U. The remaining 7 are named 174- C, E, F, H, L, N and S, like listed in the table above. 15:30 Dissolved respective aldehydes in each vial by vortexing them for 30s each. Phenanthrene-9- carboxaldehyde in vials (174C and 174K) did not make a homogenous solution. Similarly vial 174S with 4,7-Dimethoxy-1-naphthaldehyde did not make a homogenous solution even after vortexing for 3min. 19:00 Added respective amines to the vials, vortexed each for 30s.

2008-04-03
13:00 Completed addition of respective acids to each vial, vortexed for 30s each. it was noted that upon acid addition. vials containing salicylaldehyde and 3-chloroaniline (174Q, 174R) as the aldehydes and amine components instantaneously precipitated out from the solution There was no dramatic change in the solubility of 174C, however after the addition of acid to 174K, the insoluble components started to dissolve. Vial 174S containing 4,7-Dimethoxy-1-naphthaldehyde and methylamine formed a yellow precipitate upon the addition of 5-nitrosilcylic acid. 20:00 Completed addition of respective isocyanide to each vial, vortexed for 15s each. Interestingly ppts in vials 174Q, 174R turned more fluid upon the isocyanide addition. 174S showed no change. 20:40 Obtained a picture of each vial (**Day 1 series**) 21:00 Left the vials tightly capped at room temperature.

2008-04-04
11:30 Samples which remained undissolved last evening have now tuned in to homogeneous solutions. None of the solutions have formed any ppt / crystals yet. 16:45 Obtained pictures of the vial. (**Day 2 series**)

2008-04-06
15:00 Vortexed the vials for 30s each, none of the solutions have formed any precipitates.

2008-04-09
15:00 Vortexed the vials for 30s each. 174C- has formed solid

2008-04-15
20:30 Solid has appeared in 174C and 174K, no solid in other vials.

2008-04-19
18:00 Vortexed samples vials 174C & 174K for 30s each, centrifuged them for 2m and decanted the supernatant. The residue in each vial was washed with methanol (3x1ml) and set under a high vacuum pump for drying. 22:00 Removed from high vac and obtained 174C (33mg) and 174K (27mg)

2008-05-01
10:00 Obtained HNMR and CNMR

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]-[|UHFFFAOYAC] ||
 * [|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] ||
 * [|174C] || [|InChI=1/C28H27N3O5/c1-3-4-15-29-27(33)26(30(2)28(34)24-17-19(31(3 ​5)36)13-14-25(24)32)23-16-18-9-5-6-10-20(18)21-11-7-8-12-22(21)23​ /h5-14,16-17,26,32H,3-4,15H2,1-2H3,(H,29,33)] || [|RPZJNWDWTWXITK]-[|UHFFFAOYAS] ||
 * [|174K] || [|InChI=1/C34H34N2O5/c1-21-13-15-24(41-21)20-36(31(39)18-22-14-16-2 ​9(37)30(38)17-22)32(33(40)35-34(2,3)4)28-19-23-9-5-6-10-25(23)26-​ 11-7-8-12-27(26)28/h5-17,19,32,37-38H,18,20H2,1-4H3,(H,35,40)] || [|GIXHXKYXADBHHL]-[|UHFFFAOYAS] ||