488787-48-0

Basic information

• Product Name: Cyclohexanone, 3-(2,6-dimethoxy-4-pentylphenyl)-2-iodo-4-[1-methyl-1-[(triethylsilyl)oxy] ethyl]-, (3R,4R)-
• CAS NO: 488787-48-0
• Molecular Formula: C28H47IO4Si
• Molecular Weight: 602.669
• Mol File: 488787-48-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Cyclohexanone, 3-(2,6-dimethoxy-4-pentylphenyl)-2-iodo-4-[1-methyl-1-[(triethylsilyl)oxy] ethyl]-, (3R,4R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanone, 3-(2,6-dimethoxy-4-pentylphenyl)-2-iodo-4-[1-methyl-1-[(triethylsilyl)oxy] ethyl]-, (3R,4R)-(488787-48-0)
• EPA Substance Registry System: Cyclohexanone, 3-(2,6-dimethoxy-4-pentylphenyl)-2-iodo-4-[1-methyl-1-[(triethylsilyl)oxy] ethyl]-, (3R,4R)-(488787-48-0)

Safety Data

• Hazardous Substances Data: 488787-48-0(Hazardous Substances Data)

Upstream product

• 22976-40-5 1,3-dimethoxy-5-pentylbenzene 
• 488787-47-9 (R)-2-iodo-4-[(1-methyl-1-triethylsilyloxy)ethyl]-2-cyclohexen-1-one 
• 488787-46-8 (R)-4-[(1-methyl-1-triethylsilyloxy)ethyl]-2-cyclohexen-1-one 
• 488787-45-7 (R)-4-[(1-hydroxy-1-methyl)ethyl]-2-cyclohexen-1-one 
• 132042-13-8 Acetic acid 1-((R)-4-acetoxy-cyclohex-3-enyl)-1-methyl-ethyl ester 
• 135432-21-2 (R)-4-[(1-acetoxy-1-methyl)ethyl]-2-cyclohexenone 
• 127-91-3 (1R,5R)-(+)-β-pinene 
• 77982-63-9 nopinone 

Downstream Products

• 488787-50-4 (3R,4R)-3-[(2,6-dimethoxy-4-pentyl)phenyl]-1-methyl-4-[(1-methyl-1-triethylsilyloxy)ethyl]-1-cyclohexene 
• 488787-51-5 (3R,4R)-3-[(2-hydroxy-6-methoxy-4-pentyl)phenyl]-1-methyl-4-[(1-methyl-1-triethylsilyloxy)ethyl]-1-cyclohexene 
• 36403-68-6 D1,2-Tetrahydrocannabinol methyl ether 
• 1972-08-3 dronabinol 
• 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 

Relevant articles and documents

Synthesis of tetrahydrocannabinols based on an indirect 1,4-addition strategy

The synthetic procedure presented for the preparation of the title compounds requires 1,4-addition of bulky cuprates to cyclohexenones and subsequent reaction with electrophiles. However, the enolates generated by BF3·OEt2-assistance suffer from lack of nucleophilicity. To circumvent this problem, we developed an indirect method consisting of the following three steps: (1) iodination of the cyclohexenones at the α position; (2) BF3·OEt2-assisted 1,4-addition of cuprates (Ar2Cu(CN)-Li2, Ar = aryl) followed by quenching the enolates with water; (3) reaction of the α-iodo-β-arylcylohexanones thus formed with EtMgBr to generate magnesium enolates. The enolates thus generated in this way showed a high reactivity toward ClP(O)(OEt)2 to furnish enol phosphates. The aforementioned procedure was also applied to a synthesis of optically active Δ9-tetrahydrocannabinol. In addition, a naphthalene analogue of the latter compound was also synthesized in a similar way.