72312-09-5

Basic information

• Product Name: (3aR,4R,8S,8aR,9S)-9-Hydroxy-6-methoxy-3a,8,8a-trimethyl-2,3,3a,4,8,8a-hexahydro-1H-4,8-methano-azulen-5-one
• CAS NO: 72312-09-5
• Molecular Weight: 250.338
• Mol File: 72312-09-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (3aR,4R,8S,8aR,9S)-9-Hydroxy-6-methoxy-3a,8,8a-trimethyl-2,3,3a,4,8,8a-hexahydro-1H-4,8-methano-azulen-5-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3aR,4R,8S,8aR,9S)-9-Hydroxy-6-methoxy-3a,8,8a-trimethyl-2,3,3a,4,8,8a-hexahydro-1H-4,8-methano-azulen-5-one(72312-09-5)
• EPA Substance Registry System: (3aR,4R,8S,8aR,9S)-9-Hydroxy-6-methoxy-3a,8,8a-trimethyl-2,3,3a,4,8,8a-hexahydro-1H-4,8-methano-azulen-5-one(72312-09-5)

Safety Data

• Hazardous Substances Data: 72312-09-5(Hazardous Substances Data)

Upstream product

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

Downstream Products

• 41410-53-1 (+/-)-gymnomitrol 

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 bicyclooctanes 13 and 14 by ionic 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.