683247-05-4

Basic information

• Product Name: Carbamic acid, (phenylmethyl)-, (1S,2R,5S)-5-methyl-2-(1-methylethyl)cyclohexyl ester
• CAS NO: 683247-05-4
• Molecular Formula: C18H27NO2
• Molecular Weight: 289.418
• Mol File: 683247-05-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Carbamic acid, (phenylmethyl)-, (1S,2R,5S)-5-methyl-2-(1-methylethyl)cyclohexyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, (phenylmethyl)-, (1S,2R,5S)-5-methyl-2-(1-methylethyl)cyclohexyl ester(683247-05-4)
• EPA Substance Registry System: Carbamic acid, (phenylmethyl)-, (1S,2R,5S)-5-methyl-2-(1-methylethyl)cyclohexyl ester(683247-05-4)

Safety Data

• Hazardous Substances Data: 683247-05-4(Hazardous Substances Data)

Upstream product

• 7635-54-3 (+)-(1S,2R,5S)-menthylchloroformate 
• 100-46-9 benzylamine 

Downstream Products

• 189438-85-5 2-methyl-1-phenylbut-3-en-1-amine 
• 864360-62-3 (+)-N-menthyloxycarbonyl-N-but-2(E)-enylbenzylamine 

Relevant articles and documents

Asymmetric aza-[2,3]-Wittig sigmatropic rearrangements: Chiral auxiliary control and formal asymmetric synthesis of (2S, 3R, 4R)-4-hydroxy-3- methylproline and (-)-kainic acid

A survey of 16 different chiral auxiliaries and a variety of strategies found that an (-)-8-phenylmenthol ester of a glycine derived migrating group can control the absolute stereochemistry of aza-[2,3]-Wittig sigmatropic rearrangements with diastereoselectivities of ca. 3 : 1 with respect to the auxiliary. In two specific examples, ca. 50% yields of enantiomerically pure products were obtained after chromatographic purification. These were synthetically manipulated with no erosion of stereochemistry into intermediates that completed formal asymmetric syntheses of (+)-HyMePro and (-)-kainic acid. The Royal Society of Chemisrry 2005.