135503-45-6

Basic information

• Product Name: (1R,3S,5R)-6,6-dimethyl-3-(phenylseleno)bicyclo<3.1.1>heptan-2-one
• Synonyms: (1R,3S,5R)-6,6-dimethyl-3-(phenylseleno)bicyclo<3.1.1>heptan-2-one
• CAS NO: 135503-45-6
• Molecular Weight: 293.267
• Mol File: 135503-45-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (1R,3S,5R)-6,6-dimethyl-3-(phenylseleno)bicyclo<3.1.1>heptan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,3S,5R)-6,6-dimethyl-3-(phenylseleno)bicyclo<3.1.1>heptan-2-one(135503-45-6)
• EPA Substance Registry System: (1R,3S,5R)-6,6-dimethyl-3-(phenylseleno)bicyclo<3.1.1>heptan-2-one(135503-45-6)

Safety Data

• Hazardous Substances Data: 135503-45-6(Hazardous Substances Data)

Upstream product

• 38651-65-9 (1R,5S)-(+)-nopinone 
• 1666-13-3 diphenyl diselenide 
• 34837-55-3 Phenylselenyl bromide 

Downstream Products

• 149404-74-0 (4R,5R)-1-Acetoxy-4-isopropenyl-5-methyl-5-vinylcyclohex-1-ene 
• 149339-38-8 (1R,2R,5R)-2-Benzyl-6,6-dimethylbicyclo<3.1.1>hept-3-en-2-ol 
• 80-57-9 (-)-Verbenone 
• 35408-03-8 (+)-apoverbenone 

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