20303-60-0

Basic information

• Product Name: [4S,(+)]-2-Isopropylidene-4β-isopropenyl-5α-vinyl-5-methylcyclohexanone
• Synonyms: (+)-β-Elemenone;[4S,(+)]-2-Isopropylidene-4β-isopropenyl-5α-vinyl-5-methylcyclohexanone;β-Elemenone;(4S)-Trans-beta-Elemenone
• CAS NO: 20303-60-0
• Molecular Formula: C₁₅H₂₂O
• Molecular Weight: 218.33458
• Mol File: 20303-60-0.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: [4S,(+)]-2-Isopropylidene-4β-isopropenyl-5α-vinyl-5-methylcyclohexanone(CAS DataBase Reference)
• NIST Chemistry Reference: [4S,(+)]-2-Isopropylidene-4β-isopropenyl-5α-vinyl-5-methylcyclohexanone(20303-60-0)
• EPA Substance Registry System: [4S,(+)]-2-Isopropylidene-4β-isopropenyl-5α-vinyl-5-methylcyclohexanone(20303-60-0)

Safety Data

• Hazardous Substances Data: 20303-60-0(Hazardous Substances Data)

Upstream product

• 128261-62-1 (1R,4S,5R)-(+)-4,6,6-trimethyl-4-vinylbicyclo<3.1.1>heptan-2-one 
• 6902-91-6 germacrone 
• 917-54-4 methyllithium 
• 32663-53-9 10-isopropylidene-3,7-dimethyl-cyclodeca-3t,7t-dienone 
• 128261-63-2 (1R,5S)-3-phenylsulfenyl-6,6-dimethylbicyclo<2.2.1>heptanone 
• 137041-00-0 (1R,4S,5R)-3-Benzenesulfinyl-4,6,6-trimethyl-bicyclo[3.1.1]heptan-2-one 
• 137041-01-1 (1R,3RS,4S,5R)-4,6,6-Trimethyl-3-(phenylsulfonyl)-4-vinylbicyclo<3.1.1>heptan-2-one 
• 128261-67-6 (1R,5S)-4,6,6-Trimethyl-3-(phenylsulfonyl)bicyclo<3.1.1>hept-3-en-2-one 
• 128261-65-4 (1R,3RS,4S,5R)-4,6,6-Trimethyl-3-(phenylthio)bicyclo<3.1.1>heptan-2-one 
• 128261-66-5 (1R,5S)-4,6,6-trimethyl-3-(phenylthio)bicyclo<3.1.1>hept-3-en-2-one 
• 128261-64-3 (1R,5R)-6,6-Dimethyl-3-(phenylthio)bicyclo<3.1.1>hept-3-en-2-one 
• 128261-61-0 (4S,5S)-1-acetoxy-4-isopropenyl-5-methyl-5-vinyl-1-cyclohexene 
• 18172-67-3 beta-pinene 
• 38651-65-9 (1R,5S)-(+)-nopinone 

Downstream Products

• 51371-13-2 (3S,4S)-3-Methyl-4-isopropyl-3-vinyl-1-cyclohexanone 
• 515-13-9 β-elemene 
• 64373-81-5 8α-hydroxyelemol 
• 41370-57-4 (+)-8α-acetoxyelemol 
• 30824-74-9 (+/-)-Dihydrogeijeren 
• 30824-78-3 (+/-)-1α-Ethyl-1β-methyl-2β-isopropenyl-cyclohexan 
• 5173-65-9 (+/-)-1,10-Dimethyl-Δ¹⁽⁹⁾-octalin 

Relevant articles and documents

Efficient synthesis of the anticancer β-elemene and other bioactive elemanes from sustainable germacrone

Highly efficient preparations of anticancer β-elemene and other bioactive elemanes were carried out using the natural product germacrone as a renewable starting material. The syntheses were achieved in only 3-5 steps with excellent overall yields (43-54%). An enantioselective approach to these molecules is also described

A Key Intermediate for the Chiral Synthesis of Elemanoids. Synthesis of (+)-β-Elemenone

(1R,5S)-3-Phenylsulfenyl-6,6-dimethylbicycloheptanone obtained from (+)-nopinone was transformed into (1R,4S,5S)-4-methyl-4-vinylbicycloheptan-2-one, whose cyclobutane ring was cleaved with BF3*EtO2-Zn(OAc)2 in acetic anhydride to provide (4S,5S)-1-acetoxy-4-isopropenyl-5-methyl-5-vinyl-1-cyclohexene (5), the key intermediate, in a highly regio- and stereoselective manner.Regioselective introduction of a three-carbon unit to 5 with acetone followed by dehydration yielded (+)-β-elemenone.