5033-95-4

Basic information

• Product Name: 2-Propenoic acid, 3-phenyl-, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester, (2E)-
• CAS NO: 5033-95-4
• Molecular Formula: C19H26O2
• Molecular Weight: 286.414
• Mol File: 5033-95-4.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 2-Propenoic acid, 3-phenyl-, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester, (2E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenoic acid, 3-phenyl-, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester, (2E)-(5033-95-4)
• EPA Substance Registry System: 2-Propenoic acid, 3-phenyl-, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester, (2E)-(5033-95-4)

Safety Data

• Hazardous Substances Data: 5033-95-4(Hazardous Substances Data)

Upstream product

• 89-78-1 menthol 
• 140-10-3 (E)-3-phenylacrylic acid 
• 102-92-1 Cinnamoyl chloride 
• 2216-51-5 (-)-menthol 
• 102-92-1 cinnamoyl chloride 
• 141-82-2 malonic acid 
• 100-52-7 benzaldehyde 

Downstream Products

• 73249-92-0 phenyl-3 cyclohexyl-3 (oxo-2') propanoate de menthyle 
• 111832-32-7 (2S,3R)-3-Phenyl-oxirane-2-carboxylic acid (1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 73249-94-2 menthyl 5-oxo-3,5-diphenylpentanoate 
• 109761-20-8 4,5-diphenyl-2-pyrrolidone 
• 126491-58-5 β,γ-diphenyl-γ-aminobutyric acid hydrochloride 
• 114466-82-9 (E)-(-)-menthyl 2-bromocinnamate 
• 50707-54-5 (Z)-(-)-menthyl 2-bromocinnamate 
• 50896-31-6 cis-(2R,3R)-2-((-)-menthyloxycarbonyl)-3-phenylaziridine 
• 114529-82-7 trans-(2S,3R)-2-((-)-menthyloxycarbonyl)-3-phenylaziridine 
• 114529-83-8 trans-(2R,3S)-2-((-)-menthyloxycarbonyl)-3-phenylaziridine 
• 50707-55-6 cis-(2S,3S)-2-((-)-menthyloxycarbonyl)-3-phenylaziridine 
• 114466-83-0 (2S,3S)-(-)-menthyl 2-amino-3-((4-methoxybenzyl)thio)-3-phenylpropionate 

Relevant articles and documents

Conjugate addition of aryl nucleophiles to α,β-unsaturated cinnamic acid derivatives containing Evans type chiral auxiliaries

Cinnamides containing oxazolidin-2-one type auxiliaries have been prepared. A novel pathway to chiral 4-aryl-6-methyl-3,4-dihydrocoumrines via the asymmetric conjugate addition of arylmagnesium bromides to these cinnamides is described.

Antileishmanial lead structures from nature: Analysis of structure-activity relationships of a compound library derived from caffeic acid bornyl ester

Bioassay-guided fractionation of a chloroform extract of Valeriana wallichii (V. wallichii) rhizomes lead to the isolation and identification of caffeic acid bornyl ester (1) as the active component against Leishmania major (L. major) promastigotes (IC50 = 48.8 μM). To investigate the structure-activity relationship (SAR), a library of compounds based on 1 was synthesized and tested in vitro against L. major and L. donovani promastigotes, and L. major amastigotes. Cytotoxicity was determined using a murine J774.1 cell line and bone marrow derived macrophages (BMDM). Some compounds showed antileishmanial activity in the concentration range of pentamidine and miltefosine which are the standard drugs in use. In the L. major amastigote assay compounds 15, 19 and 20 showed good activity with relatively low cytotoxicity against BMDM, resulting in acceptable selectivity indices. Molecules with adjacent phenolic hydroxyl groups exhibited elevated cytotoxicity against murine cell lines J774.1 and BMDM. The Michael system seems not to be essential for antileishmanial activity. Based on the results compound 27 can be regarded as new lead structure for further structure optimization.

Highly diastereoselective synthesis of vinylcyclopropane derivatives with (-)-8-phenylmenthol as chiral auxiliary

The silylated telluronium allylide 4, generated in situ from the corresponding telluronium salt in the presence of LiTMP, reacted with (-)-8-phenylmenthyl α,β-unsaturated esters to afford trans-2-silylvinyl-trans-3-substituted cyclopropyl esters with high diastereoselectivity in high yields. The absolute configuration was determined by chemical transformation. A mechanistic rationale is proposed.