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【结 构 式】 
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【分子编号】34545 【品名】9-chloro-3-(1,1-dimethylheptyl)-1-methoxy-6,6,9-trimethyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromene; 9-chloro-3-(1,1-dimethylheptyl)-6,6,9-trimethyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromen-1-yl methyl ether 【CA登记号】 |
【 分 子 式 】C26H41ClO2 【 分 子 量 】421.06304 【元素组成】C 74.17% H 9.81% Cl 8.42% O 7.6% |
合成路线1
该中间体在本合成路线中的序号：(VI)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. The methylation of (IV) by means of methyl iodide and K2CO3 in refluxing DMF yields the methyl ether (V), which is treated with anhydrous ZnCl2 and HCl in chloroform affording the HCl adduct (VI). Finally, this compound is dehydrochlorinated to the target compound by means of potassium tricyclopentylcarbinolate (K-tcpc) in refluxing toluene.
| 【1】 Teshima, K.; et al.; J Org Chem 1971, 36, 5, 721. |
| 【2】 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 | |
| (V) | 34544 | 3-(1,1-dimethylheptyl)-6,6,9-trimethyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-1-yl methyl ether; 3-(1,1-dimethylheptyl)-1-methoxy-6,6,9-trimethyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromene | C26H40O2 | 详情 | 详情 | |
| (VI) | 34545 | 9-chloro-3-(1,1-dimethylheptyl)-1-methoxy-6,6,9-trimethyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromene; 9-chloro-3-(1,1-dimethylheptyl)-6,6,9-trimethyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromen-1-yl methyl ether | C26H41ClO2 | 详情 | 详情 |