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【结 构 式】 
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【分子编号】50713 【品名】5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenecarbaldehyde 【CA登记号】 |
【 分 子 式 】C15H20O 【 分 子 量 】216.3232 【元素组成】C 83.29% H 9.32% O 7.4% |
合成路线1
该中间体在本合成路线中的序号：(I)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.
| 【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 |