1,1,4,4-tetramethyl-6-vinyl-1,2,3,4-tetrahydronaphthalene -Drug Synthesis Database

【结构式】

【分子编号】50714

【品名】1,1,4,4-tetramethyl-6-vinyl-1,2,3,4-tetrahydronaphthalene

【CA登记号】

【分子式】C₁₆H₂₂

【分子量】214.35068

【元素组成】C 89.65% H 10.35%

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：(II)

Wittig reaction of aldehyde (I) with methylene triphenylphosphorane produced olefin (II). Oxime (IV) was prepared from methyl 4-formylbenzoate (III) by treatment with hydroxylamine. The nitrile oxide generated from imine (IV) by chlorination, followed by elimination under basic conditions, underwent a [3+2] regioselective cycloaddition with alkene (II) to produce isoxazoline (V). Oxidation of the isoxazoline ring of (V) to the corresponding isoxazole derivative (VI) was accomplished by treatment with N-bromosuccinimide. Finally, ester hydrolysis with LiOH furnished the title carboxylic acid.

参考文献中间体

合成目标

【1】 Simoni, D.; et al.; Heterocycle-containing retinoids. Discovery of a novel isoxazole arotinoid possessing potent apoptotic activity in multidrug and drug-induced apoptosis-resistant cells. J Med Chem 2001, 44, 14, 2308.

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)	50713	5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenecarbaldehyde		C₁₅H₂₀O	详情	详情
(II)	50714	1,1,4,4-tetramethyl-6-vinyl-1,2,3,4-tetrahydronaphthalene		C₁₆H₂₂	详情	详情
(III)	10170	methyl 4-formylbenzoate	1571-08-0	C₉H₈O₃	详情	详情
(IV)	19219	methyl 4-[(hydroxyimino)methyl]benzoate		C₉H₉NO₃	详情	详情
(V)	50715	methyl 4-[5-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenyl)-4,5-dihydro-3-isoxazolyl]benzoate		C₂₅H₂₉NO₃	详情	详情
(VI)	50716	methyl 4-[5-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenyl)-3-isoxazolyl]benzoate		C₂₅H₂₇NO₃	详情	详情

Extended Information