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【结 构 式】

【分子编号】10175

【品名】(E)-4-(2,5-Dimethoxyphenyl)-3-buten-2-one

【CA登记号】

【 分 子 式 】C12H14O3

【 分 子 量 】206.24136

【元素组成】C 69.89% H 6.84% O 23.27%

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)

The synthesis of [14C]-labeled piritrexim has been described: The condensation of 2,5-dimethoxybenzaldehyde (I) with acetone in aqueous NaOH gives 4-(2,5-dimethoxyphenyl)-3-(E)-buten-2-one (II), which is hydrogenated with H2 over Pd/C in methanol to give 4-(2,5-dimethoxyphenyl)-2-butanone (III). The condensation of (III) with malononitrile (IV) by means of acetic acid-sodium acetate in refluxing toluene yields 2-cyano-5-(2,5-dimethoxyphenyl)-3-methyl-2-pentenenitrile (V), which is condensed with acetic acid diethoxymethyl ester (VI) at 105 C to afford the corresponding diethoxymethyl derivative (VII). The cyclization of (VII) with 32% HBr in acetic acid affords 2-bromo-5-(2,5-dimethoxybenzyl)-4-methylpyridine-3-carbonitrile (VIII), which is finally cyclized again with [14C]-labeled guanidine (IX) by means of NaH in refluxing tert-butyl alcohol.

1 Wisowaty, J.C.; Darnofall, M.E.; Hill, J.A.; Synthesis of carbon-14 labelled piritrexim - A potential anticancer agent. J Label Compd Radiopharm 1993, 33, 12, 1119.
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) 10174 2,5-Dimethoxybenzaldehyde 93-02-7 C9H10O3 详情 详情
(II) 10175 (E)-4-(2,5-Dimethoxyphenyl)-3-buten-2-one C12H14O3 详情 详情
(III) 10176 4-(2,5-Dimethoxyphenyl)-2-butanone C12H16O3 详情 详情
(IV) 12061 Malononitrile 109-77-3 C3H2N2 详情 详情
(V) 10177 2-[3-(2,5-Dimethoxyphenyl)-1-methylpropylidene]malononitrile C15H16N2O2 详情 详情
(VI) 17661 Diethoxymethyl acetate 14036-06-7 C7H14O4 详情 详情
(VII) 10178 2-[2-(2,5-Dimethoxybenzyl)-3,3-diethoxy-1-methylpropylidene]malononitrile C20H26N2O4 详情 详情
(VIII) 10179 2-Bromo-5-(2,5-dimethoxybenzyl)-4-methylnicotinonitrile C16H15BrN2O2 详情 详情
(IX) 14790 Guanidine 113-00-8 CH5N3 详情 详情
(IX) 44601 guanidine CH5N3 详情 详情
Extended Information