(6,6-dimethyl-4-oxobicyclo[3.1.1]hept-2-en-2-yl)methyl pivalate -Drug Synthesis Database

【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.

参考文献中间体

合成目标

【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