132042-13-8

Basic information

• Product Name: Acetic acid 1-((R)-4-acetoxy-cyclohex-3-enyl)-1-methyl-ethyl ester
• Synonyms: Acetic acid 1-((R)-4-acetoxy-cyclohex-3-enyl)-1-methyl-ethyl ester
• CAS NO: 132042-13-8
• Molecular Weight: 240.299
• Mol File: 132042-13-8.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Acetic acid 1-((R)-4-acetoxy-cyclohex-3-enyl)-1-methyl-ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Acetic acid 1-((R)-4-acetoxy-cyclohex-3-enyl)-1-methyl-ethyl ester(132042-13-8)
• EPA Substance Registry System: Acetic acid 1-((R)-4-acetoxy-cyclohex-3-enyl)-1-methyl-ethyl ester(132042-13-8)

Safety Data

• Hazardous Substances Data: 132042-13-8(Hazardous Substances Data)

Upstream product

• 38651-65-9 (1R,5S)-(+)-nopinone 
• 557-34-6 zinc diacetate 
• 127-91-3 (1R,5R)-(+)-β-pinene 
• 77982-63-9 nopinone 
• 108-24-7 acetic anhydride 
• 18172-67-3 beta-pinene 

Downstream Products

• 1972-08-3 dronabinol 
• 36403-68-6 D1,2-Tetrahydrocannabinol methyl ether 
• 488787-45-7 (R)-4-[(1-hydroxy-1-methyl)ethyl]-2-cyclohexen-1-one 
• 488787-46-8 (R)-4-[(1-methyl-1-triethylsilyloxy)ethyl]-2-cyclohexen-1-one 
• 488787-47-9 (R)-2-iodo-4-[(1-methyl-1-triethylsilyloxy)ethyl]-2-cyclohexen-1-one 
• 488787-51-5 (3R,4R)-3-[(2-hydroxy-6-methoxy-4-pentyl)phenyl]-1-methyl-4-[(1-methyl-1-triethylsilyloxy)ethyl]-1-cyclohexene 
• 488787-50-4 (3R,4R)-3-[(2,6-dimethoxy-4-pentyl)phenyl]-1-methyl-4-[(1-methyl-1-triethylsilyloxy)ethyl]-1-cyclohexene 
• 488787-48-0 (R)-3-[(2,6-dimethoxy-4-pentyl)phenyl]-2-iodo-4-[(1-methyl-1-triethylsilyloxy)ethyl]-1-cyclohexanone 
• 488787-49-1 Phosphoric acid (3R,4R)-3-(2,6-dimethoxy-4-pentyl-phenyl)-4-(1-methyl-1-triethylsilanyloxy-ethyl)-cyclohex-1-enyl ester diethyl ester 
• 67119-86-2 (4R)-1-(1,3-dithianyl)-4-(2-(2-hydroxypropanyl))-2-cyclohexen-1-ol 
• 135432-21-2 (R)-4-[(1-acetoxy-1-methyl)ethyl]-2-cyclohexenone 
• 132042-18-3 (R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-3-furan-3-ylmethyl-4-isopropyl-2-phenylselanyl-cyclohexanol 
• 132042-17-2 (R)-3-Furan-3-ylmethyl-1-hydroxymethyl-4-isopropyl-2-phenylselanyl-cyclohexanol 
• 132060-16-3 ((R)-3-Furan-3-ylmethyl-4-isopropyl-cyclohex-1-enyl)-methanol 

Relevant articles and documents

Synthesis of cyclobakuchiols A, B, and C by using conformation-controlled stereoselective reactions

Cyclohexanone with the pMeOC6H4 and CH 2/C(Me) substituents at the C3 and C4-positions was prepared from (+)-β-pinene and converted to the allylic picolinate by a Masamune-Wittig reaction followed by reduction and esterification. Allylic substitution of this picolinate with Me2CuMgBr×MgBr2 in the presence of ZnI2 proceeded with γ regio- and stereoselectively to afford the quaternary carbon center on the cyclohexane ring with the CH2/CH and Me groups in axial and equatorial positions, respectively. This product was converted to cyclobakuchiol A by demethylation and to cyclobakuchiol C by epoxidation of the CH2/C(Me) group. For the synthesis of cyclobakuchiol B, the enantiomer of the above cyclohexanone derived from (-)-β-pinene was converted to the cyclohexane-carboxylate, and the derived enolate was subjected to the reaction with CH2/CHSOPh followed by sulfoxide elimination to afford the intermediate with the quaternary carbon center with MeOC(/O) and CH2/CH groups in axial and equatorial positions. The MeOC(/O) group was transformed to the Me group to complete the synthesis of cyclobakuchiol B. Control is key! Synthesis of cyclobakuchiols A and C was stereoselectively accomplished by conformation-controlled substitution of allylic picolinate with Me2CuMgBr×MgBr2/ZnI 2. On the other hand, cyclobakuchiol B was synthesized by stereoselective addition of the cyclohexanecarboxylate enolate to CH 2/CHSOPh (see scheme). Copyright

Efficient and convenient syntheses of (R)-(-)-cryptone and (S)-(-)-isopropenyl-2-cyclohexen-1-one

Starting with (+)-nopinone (3); (R)-(-)-cryptone (1) and (S)(-)-4-isopropenyl-2-cyclohexen-1-one (2) were synthesized in five steps and 42% overall yield, and four steps and 49% overall yield, respectively.

Synthesis of Racemic and Optically Active Δ9-Tetrahydrocannabinol (THC) Metabolites

The preparation of racemic and optically active Δ9-THC metabolites is described from synthon 13.Racemic synthon 13 is prepared in four steps (46percent) from Danishefsky's diene.Optically active synthon 13 is prepared from perillaldehyde via the enone 22 in six steps (23percent yield).Alternatively, nopinone can be converted to 13 in three steps (50percent yield) via a cyclobutane ring cleavage.The acid-catalyzed condensation of 13 with olivetol (6a) and subsequent conversion to 11-hydroxy and 9-carboxyl Δ9-THC metabolites 2a and 4a is described, as well as the preparation of 1',1'-dimethylheptyl THC analogues 2b, 3b, and 4 b from 5-(1',1'-dimethylheptyl)resorcinol (6c).