134655-24-6

Basic information

• Product Name: (1S,4R,5R)-4,6,6-trimethyl-4-vinylbicyclo[3.1.1]heptan-2-one
• Synonyms: (1S,4R,5R)-4,6,6-trimethyl-4-vinylbicyclo[3.1.1]heptan-2-one
• CAS NO: 134655-24-6
• Molecular Weight: 178.274
• Mol File: 134655-24-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1S,4R,5R)-4,6,6-trimethyl-4-vinylbicyclo[3.1.1]heptan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,4R,5R)-4,6,6-trimethyl-4-vinylbicyclo[3.1.1]heptan-2-one(134655-24-6)
• EPA Substance Registry System: (1S,4R,5R)-4,6,6-trimethyl-4-vinylbicyclo[3.1.1]heptan-2-one(134655-24-6)

Safety Data

• Hazardous Substances Data: 134655-24-6(Hazardous Substances Data)

Upstream product

• 38651-65-9 (1R,5S)-(+)-nopinone 

Downstream Products

• 197232-93-2 2-[(1R,2R,6R)-3-acetyloxy-1,2-dimethyl-6-(1-methylvinyl)cyclohex-3-enyl]ethyl acetate 
• 197232-95-4 2-[(1R,2S,6R)-1,2-dimethyl-6-(1-methylvinyl)-3-oxocyclohexyl]ethyl acetate 
• 197232-94-3 (2S,3R,4R)-3-(2-hydroxyethyl)-2,3-dimethyl-4-(1-methylvinyl)cyclohexan-1-one 
• 149404-74-0 (4R,5R)-1-Acetoxy-4-isopropenyl-5-methyl-5-vinylcyclohex-1-ene 

Relevant articles and documents

Efficient Synthesis of (1S,5S)-4-Alkyl-6,6-dimethylbicyclohept-3-en-2-ones from (1R,5S)-(+)-Nopinone and Preparation of Some Chiral Building Blocks Suitable for the Asymmetric Synthesis

A general and convenient transformation of (1R,5S)-(+)-nopinone (1) into (1S,5S)-4-alkyl-6,6-dimethylbicyclohept-3-en-2-ones, i.e. (-)-verbenone (6a) as the simplest compound and its C(4)-alkyl homologs 6b-f, via (+)-apoverbenone (7) is developed and applied, starting with 6a,e, to the syntheses of (4R,5R)-1-acetoxy-4-isopropenyl-5-methyl-5-vinyl-1-cyclohexene (12a) and (4R,5S)- and (4R,5R)-1-acetoxy-5-(3-butenyl)-4-isopropenyl-5-methyl-1-cyclohexene (12b and 12c), in connection with a search for chiral building blocks suitable for the asymmetric synthesis.Preparation of 12a indicates the formal synthesis of the elemanoid sesquiterpenes (-)-β-elemenone and (-)-eleman-8β,12-olide