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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Trans-Cinnamaldehyde is a natural product isolated from cinnamon essential oil, role as a hypoglycemic agent, a phenylalanine ammonia-lyase inhibitor, a vasodilator agent, an antifungal agent, a flavouring agent, a plant metabolite and a sensitiser.
Synonyms: Cinnamaldehyde
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| CAS No. : | 14371-10-9 |
| Formula : | C9H8O |
| M.W : | 132.16 |
| SMILES Code : | O=C/C=C/C1=CC=CC=C1 |
| Synonyms : |
Cinnamaldehyde
|
| MDL No. : | MFCD00007000 |
| InChI Key : | KJPRLNWUNMBNBZ-QPJJXVBHSA-N |
| Pubchem ID : | 637511 |
| GHS Pictogram: |
|
| Signal Word: | Warning |
| Hazard Statements: | H315-H317-H319-H335 |
| Precautionary Statements: | P261-P280-P305+P351+P338 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

[ 14371-10-9 ]
[ 931-53-3 ]
[ 1709-59-7 ]
[ 79-11-8 ]
[ 14371-10-9 ]
[ 71510-95-7 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; potassium acetate; In 2,2,2-trifluoroethanol; at 20℃; for 14h; | General procedure: In a round bottom flask, unsaturated aldehyde 2 (0.25 mmol, 1 equiv), amidomalonate 1 (0.3 mmol, 1.2 equiv), catalyst (0.05 mmol, 20% mol), and KOAc (0.3 mmol, 1.2 equiv) were added sequentially in 1 mL of 2,2,2-trifluoroethanol. The reaction was stirred at room temperature overnight. Then the crude was purified by column chromatography to furnish piperidine adducts 3. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| In ethanol; at 60℃; for 0.5h; | General procedure: A mixture of corresponding hydrazinylpyridazine 1 or 5 (1 mmol) and aldehyde 2 (1.1 mmol) in ethanol (5 mL) was heated at 60 oC for 0.5 h. The formation of hydrazone was checked by TLC and the reaction mixture was cooled to rt. Oxone (1.5 mmol) was added to the mixture at rt followed by tetramethyl ammonium bromide (0.2 mmol) and the resulting mixture was heated at 60 oC for another 5 h. The mixture was cooled to rt and extracted with dichloromethane (2 × 25 mL), dried over anhydrous sodium sulphate and concentrated to obtain a residue which was purified by column chromatography using hexane/ethyl acetate as eluent to furnish the desired triazolopyridazines 4 and 7. |
[ 14371-10-9 ]
[ 6971-45-5 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 54% | In methanol; at 20℃; for 0.25h; | Cinnamaldehyde (5.0 mmol, 1.0 equiv) was added dropwise to a solution of o-methoxyphenylhydrazine hydrochloride (5.0 mmol, 1.0 equiv) in MeOH (2 mL), and the mixture was stirred for 15 min at ambient temperature. After the solvent was removed in vacuo, the residue was diluted with CHCl3 (10 mL). The organic layer was separated, washed with sat. NaHCO3 aq. (10 mL) and brine (10 mL), dried over Na2SO4 and the solvent was removed in vacuo. The residue was purified by recrystallization in MeOH to give the pure hydrazone 1d. |
[ 14371-10-9 ]
[ 6281-32-9 ]



[ 14371-10-9 ]

[ 13380-67-1 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 80% | In toluene; at 25℃; for 6h; | General procedure: To a suspension of the corresponding polisubstituted prolineexo-1 (100 mg, 0.32 mmol) in toluene was added dropwisethe corresponding aldehyde or ketone (1 equiv.). After5 minutes was added the dipolarophile (1.1 equiv.) and thereaction mixture was checked by TLC (hexane:ethyl acetate,8:2). The resultant solution was dried under vacuum and thecrude residue was purified by column chromatography (hexane:ethyl acetate, 8:2). Time and temperatures of the differentreaction are collected in the table. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 76% | General procedure: To a stirred solution of (S)-N-((3-methylpyridin-2-yl)carbamothioyl) pyrrolidine-2-carboxamide (0.10 mmol), α,β-unsaturated aldehyde (1.0 mmol) and 4 Å MS (0.1 g) in CH2Cl2 (20 mL) were added and stirred at room temperature for 10 min. Next, O-nitrobenzoic acid (0.10 mmol) and the salicylaldehyde derivative (1.20 mmol) were added slowly over 10 min. The mixture was stirred for indicated time at room temperature. The corresponding 2-aryl-2H-chromenes-3-carbaldehyde was separated and purified by silica gel chromatography. The ee value of the product was determined by specific rotation and chiral HPLC analysis. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 65% | With pyrrolidine; silver hexafluoroantimonate; para-tert-butylphenol; potassium carbonate; In chloroform; at 80℃; for 12h;Inert atmosphere; | In a 25 ml round bottom flask, add cinnamaldehyde 1a (0.25 mmol, 33 mg), <strong>[14447-15-5]propyl cyanoacetate</strong> 2c (2 mmol, 254 mg), potassium carbonate (0.5 mmol, 69 mg), silver hexafluoroantimonate (0.05 mmol, 17 mg), tetrahydropyrrole (0.05 mmol, 4 mg), p-tert-butylphenol (0.025 mmol, 4 mg), dissolved in 3 ml of chloroform, 80 C under nitrogen protection Stir for 12 hours. After the reaction was completed, the mixed solution was cooled to room temperature, extracted three times with saturated brine and dichloromethane (10 ml / time), and the organic phases were combined and dried over anhydrous sodium sulfate. Finally, it is separated by silica gel column chromatography (eluent is petroleum ether and ethyl acetate, the volume ratio is 30: 1-20: 1) to obtain the target product polysubstituted benzene 3ac (yield 65%). |