82022-31-9

Basic information

• Product Name: (3aR,4S,8R,8aR)-6-Methoxy-3a,8,8a-trimethyl-2,3,3a,4,8,8a-hexahydro-1H-4,8-methano-azulene-5,9-dione
• CAS NO: 82022-31-9
• Molecular Weight: 248.322
• Mol File: 82022-31-9.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (3aR,4S,8R,8aR)-6-Methoxy-3a,8,8a-trimethyl-2,3,3a,4,8,8a-hexahydro-1H-4,8-methano-azulene-5,9-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (3aR,4S,8R,8aR)-6-Methoxy-3a,8,8a-trimethyl-2,3,3a,4,8,8a-hexahydro-1H-4,8-methano-azulene-5,9-dione(82022-31-9)
• EPA Substance Registry System: (3aR,4S,8R,8aR)-6-Methoxy-3a,8,8a-trimethyl-2,3,3a,4,8,8a-hexahydro-1H-4,8-methano-azulene-5,9-dione(82022-31-9)

Safety Data

• Hazardous Substances Data: 82022-31-9(Hazardous Substances Data)

Upstream product

• 765-47-9 1,2-dimethylcyclopentene 
• 72312-08-4 2-methyl-4,4,5-trimethoxycyclohexa-2,5-dienone 

Relevant articles and documents

A synthesis of gymnomitrol

Condensation of 1,2 - dimethylcyclopentene 10 with 2 - methyl - 4,4, 5 - trimethoxycyclohexa - 2,5 -dienone 7 in methylene chloride - nitromethane with added stannic chloride gave a mixture of the two diastereomeric bicycle[3.2.1]octanes 13 and 14 by ionic [4+2]cycloaddition. After selective reduction of the saturated carbonyl group with sodium borohydride, and hydrogenation of the double bond the two epimers 18 and 20 (ratio 3.3:1) were separable by chromatography. Protection of the hydroxy group in 18 with dihydropyran and, reduction of the α-methoxyketone 19 with calcium in liquid ammonia gave ketone 21. Gymnomitrol 1 was then prepared by Wittig olefination followed by deprotection of the hydroxy group.