92180-13-7

Basic information

• Product Name: (-)-menthyl (Z)-3-chloroacrylate
• Synonyms: (-)-menthyl (Z)-3-chloroacrylate
• CAS NO: 92180-13-7
• Molecular Weight: 244.762
• Mol File: 92180-13-7.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (-)-menthyl (Z)-3-chloroacrylate(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-menthyl (Z)-3-chloroacrylate(92180-13-7)
• EPA Substance Registry System: (-)-menthyl (Z)-3-chloroacrylate(92180-13-7)

Safety Data

• Hazardous Substances Data: 92180-13-7(Hazardous Substances Data)

Upstream product

• 1609-93-4 3-chloroacrylic acid 
• 2216-51-5 (-)-menthol 

Downstream Products

• 92180-27-3 menthyl trans-(2,2-diethoxycarbonyl-4-isopropenyl-1-trifluoroacetylpyrrolidin-3-yl)acetate 
• 77632-78-1 (-)-menthyl(Z)-4,4-diethoxycarbonyl-4--2-butenoate 
• 92180-18-2 (-)-menthyl(Z)-4,4-diethoxycarbonyl-4-trifluoroacetamido-2-butenoate 

Relevant articles and documents

High Asymmetric Induction in Lewis Acid-Promoted Intramolecular Ene-Type Reactions: A Diastereo- and Enantioselective Synthesis of (+)-α-Alolokainic Acid

The monocyclic amino diacid (+)-α-allokainic acid 1 has been prepared enantioselectively from the ester of cis-β-chloroacrylic acid and (-)-8-phenylmenthol by a series of four synthetic operations in over 15percent yield.The crucial step is the intramolecular 'ene-type' reaction of the (Z)-diene 4 which on treatment with a mild Lewis acid undergoes a highly accelerated, dia- and enantiostereoselective cyclization to give the pyrrolidines 6 and 7 in a ratio of 95:5 (Scheme 3).Subsequent ester hydrolysis regenerates the auxiliary chiral alcohol.Similar cyclization of the (E)-diene 5 furnished a 15:85 mixture of 6 and 7 showing an efficient reversal of the optical induction by variation of the enoate geometry.