4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol -Drug Synthesis Database

【结构式】

【分子编号】34543

【品名】4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol

【CA登记号】

【分子式】C₁₀H₁₆O

【分子量】152.23644

【元素组成】C 78.9% H 10.59% O 10.51%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(II)

参考文献中间体

合成目标

【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

合成路线2

该中间体在本合成路线中的序号：(II)

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.

参考文献中间体

合成目标

【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

Extended Information