488787-45-7

Upstream product

• 135432-21-2 (R)-4-[(1-acetoxy-1-methyl)ethyl]-2-cyclohexenone 
• 132042-13-8 Acetic acid 1-((R)-4-acetoxy-cyclohex-3-enyl)-1-methyl-ethyl ester 
• 67119-85-1 (+/-)-4-(1-hydroxy-1-methylethyl)cyclohex-2-enone 
• 488787-31-1 6-[(1-hydroxy-1-methyl)ethyl]-3-ethoxy-2-cyclohexen-1-one 
• 5323-87-5 3-Ethoxycyclohex-2-en-1-one 
• 127-91-3 (1R,5R)-(+)-β-pinene 
• 77982-63-9 nopinone 

Downstream Products

• 488787-46-8 (R)-4-[(1-methyl-1-triethylsilyloxy)ethyl]-2-cyclohexen-1-one 
• 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 
• 488787-48-0 (R)-3-[(2,6-dimethoxy-4-pentyl)phenyl]-2-iodo-4-[(1-methyl-1-triethylsilyloxy)ethyl]-1-cyclohexanone 
• 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 
• 488787-47-9 (R)-2-iodo-4-[(1-methyl-1-triethylsilyloxy)ethyl]-2-cyclohexen-1-one 
• 36403-68-6 D1,2-Tetrahydrocannabinol methyl ether 
• 1972-08-3 dronabinol 

Relevant academic research and scientific papers

Cannabidiol derivative as well as preparation method and medical application thereof

The invention relates to a cannabidiol derivative and application thereof in medicine, in particular to a pyrimidine derivative as shown in a general formula (I), or a stereoisomer, a solvate, a metabolite, a prodrug, a pharmaceutically acceptable salt or a co-crystal thereof, and definition of each substituent in the general formula (I) is the same as that in the specification.

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.