92180-15-9

Basic information

• Product Name: (-)-menthyl (E)-3-chloroacrylate
• Synonyms: (-)-menthyl (E)-3-chloroacrylate
• CAS NO: 92180-15-9
• Molecular Weight: 244.762
• Mol File: 92180-15-9.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (-)-menthyl (E)-3-chloroacrylate(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-menthyl (E)-3-chloroacrylate(92180-15-9)
• EPA Substance Registry System: (-)-menthyl (E)-3-chloroacrylate(92180-15-9)

Safety Data

• Hazardous Substances Data: 92180-15-9(Hazardous Substances Data)

Upstream product

• 2345-61-1 (E)-3-chloroacrylic acid 
• 2216-51-5 (-)-menthol 

Downstream Products

• 92180-18-2 (-)-menthyl(E)-4,4-diethoxycarbonyl-4-trifluoroacetamido-2-butenoate 
• 92180-27-3 (3R,4R)-4-Isopropenyl-3-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxycarbonylmethyl)-1-(2,2,2-trifluoro-acetyl)-pyrrolidine-2,2-dicarboxylic acid diethyl ester 
• 92180-27-3 menthyl trans-(2,2-diethoxycarbonyl-4-isopropenyl-1-trifluoroacetylpyrrolidin-3-yl)acetate 
• 77632-78-1 (-)-menthyl(E)-4,4-diethoxycarbonyl-4--2-butenoate 

Relevant articles and documents

ENANTIOSELECTIVE SYNTHESIS OF (+)-α-ALLOKAINIC ACID BY ASYMMETRIC LEWIS ACID-MEDIATED INTRAMOLECULAR ENE REACTION

(+)-α-Allokainic acid ((+)-1) has been prepared for the ester of cis-β-chloroacrylic acid and (-)-8-phenylmenthol by a sequence of four synthetic operations.The crucial step 8d-14d (Scheme 4) is a 100percent diastereo- and 90percent enantioselective intramolecular ene reaction proceeding at -35 degC on treatment of 8d with Me2AlCl.Saponification of 14d regenerated the auxiliary chiral alcohol and yielded (+)-1 on subsequent decarboxylation.In the analogous cyclization 11d-15d the sense of asymmetric induction (78percent d.e.) was opposite as confirmed by the conversion of 15d to (-)-α-allokainic acid.