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【结 构 式】

【药物名称】L-759633

【化学名称】3-(1,1-Dimethylheptyl)-1-methoxy-6,6,9-trimethyl-6a,7,10,10a-tetrahydrobenzo[c]-6H-1-benzopyran

【CA登记号】

【 分 子 式 】C26H40O2

【 分 子 量 】384.6075

【开发单位】Merck Frosst (Originator)

【药理作用】PHARMACOLOGICAL TOOLS, Cannabinoid CB2 Agonists

合成路线1

The title compound was obtained by methylation of phenol (I), which was prepared from pinene.

1 Tremblay, N.; Labelle, M.; Rochette, C.; Dufresne, C.; Gallant, M.; Gareau, Y.; Metters, K.M.; Sawyer, N.; Slipetz, D.M.; Weech, P.K.; Structure activity relatioships of tetrahydrocannabibol analogues on human cannabinoid receptors. Bioorg Med Chem Lett 1996, 6, 2, 189.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 31571 3-(1,1-dimethylheptyl)-6,6,9-trimethyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-1-ol C25H38O2 详情 详情

合成路线2

The cyclization of aldehyde (I) or verbenol (II) with resorcinol (III) by means of BF3 in dichloromethane gives the tetrahydrocannabiol analoge (IV) after column chromatography purification. Finally, this product is methylated by means of methyl iodide and K2CO3 in refluxing DMF.

1 Tremblay, N.; Labelle, M.; Rochette, C.; Dufresne, C.; Gallant, M.; Gareau, Y.; Metters, K.M.; Sawyer, N.; Slipetz, D.M.; Weech, P.K.; Structure activity relatioships of tetrahydrocannabibol analogues on human cannabinoid receptors. Bioorg Med Chem Lett 1996, 6, 2, 189.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 34542 (2E)-3,7-dimethyl-2,6-octadienal 5392-40-5 C10H16O 详情 详情
(II) 34543 4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol C10H16O 详情 详情
(III) 20233 5-(1,1-dimethylheptyl)-1,3-benzenediol C15H24O2 详情 详情
(IV) 31571 3-(1,1-dimethylheptyl)-6,6,9-trimethyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-1-ol C25H38O2 详情 详情
Extended Information