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Chemical Structure| 14371-10-9 Chemical Structure| 14371-10-9
Chemical Structure| 14371-10-9

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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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Product Details of trans-Cinnamaldehyde

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

Safety of trans-Cinnamaldehyde

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H317-H319-H335
Precautionary Statements:P261-P280-P305+P351+P338

Application In Synthesis of trans-Cinnamaldehyde

* 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.

  • Downstream synthetic route of [ 14371-10-9 ]

[ 14371-10-9 ] Synthesis Path-Downstream   1~31

  • 1
  • [ 14371-10-9 ]
  • [ 69583-00-2 ]
  • [ 101284-85-9 ]
  • 2
  • [ 14371-10-9 ]
  • [ 108-24-7 ]
  • [ 122-72-5 ]
  • 3
  • [ 2346-00-1 ]
  • [ 14371-10-9 ]
  • [ 55089-95-7 ]
  • 4
  • [ 14371-10-9 ]
  • [ 1794-45-2 ]
  • 5
  • [ 14371-10-9 ]
  • [ 931-53-3 ]
  • [ 1709-59-7 ]
  • [ 79-11-8 ]
  • (E)-2-[(2-Chloro-acetyl)-(4-dimethylsulfamoyl-phenyl)-amino]-4-phenyl-but-3-enoic acid cyclohexylamide [ No CAS ]
  • 7
  • [ 14371-10-9 ]
  • [ 6972-82-3 ]
  • [ 343362-39-0 ]
  • 8
  • [ 14371-10-9 ]
  • [ 107-91-5 ]
  • [ 19006-81-6 ]
  • 9
  • [ 1824-81-3 ]
  • [ 14371-10-9 ]
  • [ 40299-87-4 ]
  • (E)-3-(6-Methyl-pyridin-2-ylamino)-1-morpholin-4-yl-5-phenyl-pent-4-en-1-one [ No CAS ]
  • 10
  • [ 14371-10-9 ]
  • [ 40299-87-4 ]
  • [ 2836-03-5 ]
  • (E)-3-(2-Dimethylamino-phenylamino)-1-morpholin-4-yl-5-phenyl-pent-4-en-1-one [ No CAS ]
  • 11
  • [ 14371-10-9 ]
  • [ 40299-87-4 ]
  • [ 90-04-0 ]
  • (E)-3-(2-Methoxy-phenylamino)-1-morpholin-4-yl-5-phenyl-pent-4-en-1-one [ No CAS ]
  • 12
  • [ 14371-10-9 ]
  • [ 40299-87-4 ]
  • [ 120-71-8 ]
  • (E)-3-(2-Methoxy-5-methyl-phenylamino)-1-morpholin-4-yl-5-phenyl-pent-4-en-1-one [ No CAS ]
  • 13
  • [ 4187-87-5 ]
  • [ 292638-84-7 ]
  • [ 14371-10-9 ]
  • [ 90-63-1 ]
  • 14
  • [ 14371-10-9 ]
  • [ 80-65-9 ]
  • [ 860006-45-7 ]
  • 15
  • [ 14371-10-9 ]
  • [ 175883-62-2 ]
  • C17H18O2 [ No CAS ]
  • C17H18O2 [ No CAS ]
  • 16
  • [ 14371-10-9 ]
  • [ 57497-39-9 ]
  • [ 90331-02-5 ]
  • 17
  • [ 14371-10-9 ]
  • [ 124755-24-4 ]
  • C17H17F6O5P [ No CAS ]
  • C17H17F6O5P [ No CAS ]
  • 18
  • [ 14371-10-9 ]
  • [ 71510-95-7 ]
  • (3R,4S,6S)-ethyl 6-hydroxy-1-methyl-2-oxo-4-phenylpiperidine-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation 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.
  • 19
  • [ 14371-10-9 ]
  • [ 56291-51-1 ]
  • [ 1419403-33-0 ]
  • 20
  • [ 14371-10-9 ]
  • [ 38956-79-5 ]
  • 6-methyl-3-[(E)-2-phenylethenyl][1,2,4]triazolo[4,3-b]pyridazine [ No CAS ]
  • 21
  • [ 14371-10-9 ]
  • [ 38956-79-5 ]
  • C14H14N4 [ No CAS ]
YieldReaction ConditionsOperation 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.
  • 22
  • [ 14371-10-9 ]
  • [ 570-02-5 ]
  • (Z)-3-(2,4,6-trimethoxyphenyl)-3-phenylacrylaldehyde [ No CAS ]
  • (E)-3-(2,4,6-trimethoxyphenyl)-3-phenylacrylaldehyde [ No CAS ]
  • 23
  • [ 14371-10-9 ]
  • [ 21906-39-8 ]
  • 2-methyl-4-phenyl-3-(3-(trifluoromethyl)phenyl)pyridine [ No CAS ]
  • 24
  • [ 14371-10-9 ]
  • [ 6971-45-5 ]
  • (E)-1-(2-methoxyphenyl)-2-((E)-3-phenylallylidene)hydrazone [ No CAS ]
YieldReaction ConditionsOperation 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.
  • 25
  • [ 14371-10-9 ]
  • [ 6971-45-5 ]
  • 1-(2-methoxyphenyl)-5-phenylpyrazole [ No CAS ]
  • 26
  • [ 14371-10-9 ]
  • [ 6281-32-9 ]
  • C19H17NO2 [ No CAS ]
  • C19H17NO2 [ No CAS ]
  • C19H17NO2 [ No CAS ]
  • C19H17NO2 [ No CAS ]
  • 27
  • [ 14371-10-9 ]
  • [ 6281-32-9 ]
  • C19H17NO2 [ No CAS ]
  • C19H17NO2 [ No CAS ]
  • 28
  • [ 14371-10-9 ]
  • [ 14847-51-9 ]
  • 6-methyl-2-phenylbenzofuran-3-carbaldehyde [ No CAS ]
  • 29
  • [ 14371-10-9 ]
  • (2S,3S,4R,5S)-4-nitro-3,5-diphenylpyrrolidine-2-carboxylic acid [ No CAS ]
  • [ 13380-67-1 ]
  • (3aR,4R,6S,7R,8S,8aS,8bS)-2-(4-bromophenyl)-7-nitro-6,8-diphenyl-4-[(E)-styryl]hexahydropyrrolo[3,4-a]pyrrolizine-1,3(2H,8bH)-dione [ No CAS ]
YieldReaction ConditionsOperation 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.
  • 30
  • [ 14371-10-9 ]
  • [ 2631-77-8 ]
  • C16H10I2O2 [ No CAS ]
YieldReaction ConditionsOperation 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.
  • 31
  • [ 14371-10-9 ]
  • [ 14447-15-5 ]
  • C17H16N2O2 [ No CAS ]
YieldReaction ConditionsOperation 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%).
 

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