89064-06-2

Basic information

• Product Name: 2-Cyclohexen-1-one, 3-methyl-4-(1-methylethenyl)-, (S)-
• CAS NO: 89064-06-2
• Molecular Formula: C10H14O
• Molecular Weight: 150.221
• Mol File: 89064-06-2.mol

Chemical Properties

• CAS DataBase Reference: 2-Cyclohexen-1-one, 3-methyl-4-(1-methylethenyl)-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Cyclohexen-1-one, 3-methyl-4-(1-methylethenyl)-, (S)-(89064-06-2)
• EPA Substance Registry System: 2-Cyclohexen-1-one, 3-methyl-4-(1-methylethenyl)-, (S)-(89064-06-2)

Safety Data

• Hazardous Substances Data: 89064-06-2(Hazardous Substances Data)

Upstream product

• 75-16-1 methylmagnesium bromide 
• 89002-23-3 (R)-(+)-4-(2-propenyl)-2-cyclohexen-1-one 
• 18309-32-5 Verbenone 
• 557-34-6 zinc diacetate 
• 225221-32-9 (R)-(-)-1-acetoxy-4-isopropenyl-5-(methylene)cyclohexene 
• 64243-08-9 (+)-(1R,5R)-2⁽¹⁰⁾-Pinen-4-on 
• 225221-30-7 (R)-(-)-1-acetoxy-4-(1-acetoxy-1-methylethyl)-5-(methylene)cyclohexene 
• 930-68-7 cyclohexenone 
• 89064-04-0 (1S,2S,6R)-7-oxabicyclo[4.1.0]heptan-2-ol 
• 6426-26-2 (S)-cyclohex-2-en-1-ol 
• 89002-21-1 (1R,4R)-4-isopropenyl-2-cyclohexen-1-ol 
• 89064-05-1 (3S,4R)-3,4-epoxy-1-cyclohexene 

Downstream Products

• 116724-19-7 (S)-(-)-4-isopropyl-3-methyl-2-cyclohexen-1-one 
• 51371-13-2 (3S,4S)-3-Methyl-4-isopropyl-3-vinyl-1-cyclohexanone 
• 89064-07-3 (4S,5S)-2-(Bis-methylsulfanyl-methylene)-4-isopropenyl-5-methyl-5-vinyl-cyclohexanone 

Relevant articles and documents

BF3-induced cyclobutane-opening of verbenone and its deconjugate homolog. Efficient preparation of o-mentha-1,8-dien-3-one and o-menth-1-en- 3-one in optically active forms

Starting with (+)-verbenone, readily obtainable from (+)-nopinone, enantioselective preparation of (S)-(+)-4-isopropenyl-, (S)-(-)-4-isopropyl- and (R)-(+)-4-(1-acetoxy-1-methylethyl)-3-methyl-2-cyclohexen-1-ones was accomplished with little loss of stereochemical integrity via BF3-induced cyclobutane-opening of (+)4-(methylene)nopinone. As we have developed an efficient chemical transformation of (+)-nopinone into (-)-verbenone, the present syntheses of the above cyclohexenones are formal syntheses of their enantiomers from (+)-nopinone.

STEREOSELECTIVE TOTAL SYNTHESIS OF (4S)-trans-β-ELEMENONE FROM (S)-2-CYCLOHEXEN-1-OL

Stereoselective first total synthesis of (4S)-trans-β-elemenone was achieved from (S)-2-cyclohexen-1-ol, prepared easily by the asymmetric reduction of 2-cyclohexen-1-one with chiral hydride reagent.