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【结 构 式】

【分子编号】44157

【品名】(6,6-dimethyl-4-oxobicyclo[3.1.1]hept-2-en-2-yl)methyl pivalate

【CA登记号】

【 分 子 式 】C15H22O3

【 分 子 量 】250.33788

【元素组成】C 71.97% H 8.86% O 19.17%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(IV)

Esterification of (1S,5R)-myrtenol (I) with pivalyl chloride (II) yields ester (III), which is then oxidized with Na2CrO4 in HOAc-Ac2O to give 4-oxo-myrtenyl pivalate (IV). Reduction of (IV) with lithium tri-t-butoxyaluminohydride in THF affords 4-hydroxymyrtenyl pivalate (V), which is then condensed with 5-(1,1-dimethylheptyl)resorcinol (VI) in the presence of p-TsOH in CH2Cl2 to furnish compound (VII). Treatment of (VII) with K2CO3 in MeOH provides methyl ether derivative (VIII), which is finally reduced with LiAlH4.

1 Mechoulam, R.; et al.; Synthesis of the individual, pharmacologically distinct, enantiomers of a tetrahydrocannabinol derivative. Tetrahedron Asymmetry 1990, 1, 5, 315.
2 Goldenberg, D.; Horowitz, M.; Hanus, L.; Breuer, A.; Ross, R.A.; Pertwee, R.G.; Mechoulam, R.; Shiloah, S.; Tchilibon, S.; Fride, E.; HU - 308: A specific agonist for CB2, a peripheral cannabinoid receptor. Proc Natl Acad Sci USA 1999, 96(25): 14228 1999, 96, 25, 14228.
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) 44155 (6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methanol 515-00-4 C10H16O 详情 详情
(II) 13597 2,2-Dimethylpropanoyl chloride; Pivaloyl chloride 3282-30-2 C5H9ClO 详情 详情
(III) 44156 (6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methyl pivalate C15H24O2 详情 详情
(IV) 44157 (6,6-dimethyl-4-oxobicyclo[3.1.1]hept-2-en-2-yl)methyl pivalate C15H22O3 详情 详情
(V) 44158 [(4R)-4-hydroxy-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]methyl pivalate C15H24O3 详情 详情
(VI) 20233 5-(1,1-dimethylheptyl)-1,3-benzenediol C15H24O2 详情 详情
(VII) 44159 [(4R)-4-[4-(1,1-dimethylheptyl)-2,6-dihydroxyphenyl]-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]methyl pivalate C30H46O4 详情 详情
(VIII) 44160 [(4R)-4-[4-(1,1-dimethylheptyl)-2,6-dimethoxyphenyl]-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]methyl pivalate C32H50O4 详情 详情
Extended Information