13567-45-8

Basic information

• Product Name: 1H-3a,7-Methanoazulen-5-ol,octahydro-3,6,8,- 8-tetramethyl-,(3R,3aR,5S,6S,7S,8aS)-
• CAS NO: 13567-45-8
• Molecular Weight: 222.371
• Mol File: 13567-45-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 1H-3a,7-Methanoazulen-5-ol,octahydro-3,6,8,- 8-tetramethyl-,(3R,3aR,5S,6S,7S,8aS)- (CAS DataBase Reference)
• NIST Chemistry Reference: 1H-3a,7-Methanoazulen-5-ol,octahydro-3,6,8,- 8-tetramethyl-,(3R,3aR,5S,6S,7S,8aS)- (13567-45-8)
• EPA Substance Registry System: 1H-3a,7-Methanoazulen-5-ol,octahydro-3,6,8,- 8-tetramethyl-,(3R,3aR,5S,6S,7S,8aS)- (13567-45-8)

Safety Data

• Hazardous Substances Data: 13567-45-8(Hazardous Substances Data)

Upstream product

• 87017-57-0 9-hydroxy-2,8-dimethyltricyclo<5.3.1.0^1,5>undecane-6-spiro-1'-cyclopropane 
• 87017-57-0 C₁₅H₂₄O 
• 13567-40-3 5-cedranone 
• 469-61-4 α-Cedrene 

Downstream Products

• 13567-40-3 5-cedranone 
• 13794-73-5 (3R,3aR,6S,7S,8aS)-3,6,8,8-tetramethylhexahydro-1H-3a,7-cedaran-5(4H)-one 
• 469-61-4 alpha-cedrene 
• 469-61-4 (+/-)-2-epi-methyl-α-cedrene 
• 469-61-4 (+/-)-cedrene 

Relevant articles and documents

Bicyclooctenones in Synthesis. A New Synthesis of (+/-)-Cedrene using Sequential Inter- and Intra-molecular Michael Reactions

A new synthetic approach to cedrene (1) based on sequential inter- and intra-molecular Michael reactions using the bicyclooctenone (21) as the key intermediate is described.Michael addition of the enolate derived from (21) to 2-nitrobut-2-ene, led to a mixture of diastereoisomers of the nitro ketone (22), which was then converted into the 1,4-dione (23).Treatment of (23) with potassium t-butoxide in t-butyl alcohol resulted in smooth intramolecular Michael reaction leading to a mixture of α- (24a; major) and β-isomers of the tricyclo1,5>undecanedione (24) in a combined yield of 73percent.The undecanedione (24) was then converted into (+/-)-cedrene (1) and the corresponding methyl epimer (31a) via the intermediates (25), (26), (27), and (28).