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【结 构 式】

【分子编号】56191

【品名】1-[3,5-di(tert-butyl)phenyl]-1-ethanone

【CA登记号】

【 分 子 式 】C16H24O

【 分 子 量 】232.36596

【元素组成】C 82.7% H 10.41% O 6.89%

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)

Addition of methyllithium to 3,5-di-tert-butylbenzoic acid (I) at -78 C gave acetophenone (II). The Horner-Emmons condensation of acetophenone (II) with diethyl (cyanomethyl)phosphonate (III) resulted in a mixture of isomeric alpha,beta-unsaturated nitriles (IV). After isolation of the major E-isomer by preparative TLC, cyano group reduction employing DIBAL in CH2Cl2 at -78 C provided aldehyde (V). This was subjected to a new Horner-Emmons condensation with phosphonate (VI) to provide the octatrienoate ester (VII). The target carboxylic acid was then prepared by saponification of ester (VII) with methanolic KOH.

1 Zhang, L.; et al.; Discovery of novel retinoic acid receptor agonists having potent antiproliferative activity in cervical cancer cells. J Med Chem 1996, 39, 14, 2659.
2 Boehm, M.F.; Zhang, L.; Bennani, Y.L.; Nadzan, A.M. (Ligand Pharmaceuticals, Inc.); Novel trienoic retinoid cpds. and methods. JP 1998511948; US 5721103; US 6083977; WO 9620913 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IVa) 56192 (E)-3-[3,5-di(tert-butyl)phenyl]-2-butenenitrile C18H25N 详情 详情
(IVb) 56193 (Z)-3-[3,5-di(tert-butyl)phenyl]-2-butenenitrile C18H25N 详情 详情
(I) 56190 3,5-Di-tert-butylbenzoic acid 16225-26-6 C15H22O2 详情 详情
(II) 56191 1-[3,5-di(tert-butyl)phenyl]-1-ethanone C16H24O 详情 详情
(III) 10045 Diethyl cyanomethylphosphonate 2537-48-6 C6H12NO3P 详情 详情
(V) 56194 (E)-3-[3,5-di(tert-butyl)phenyl]-2-butenal C18H26O 详情 详情
(VI) 44704 ethyl (E)-4-(diethoxyphosphoryl)-3-methyl-2-butenoate 41891-54-7 C11H21O5P 详情 详情
(VII) 56195 ethyl (2E,4E,6E)-7-[3,5-di(tert-butyl)phenyl]-3-methyl-2,4,6-octatrienoate C25H36O2 详情 详情
Extended Information