【结 构 式】 |
【分子编号】36085 【品名】7-(4-chlorophenyl)-2-(ethoxycarbonyl)heptanoic acid 【CA登记号】 |
【 分 子 式 】C16H21ClO4 【 分 子 量 】312.79304 【元素组成】C 61.44% H 6.77% Cl 11.33% O 20.46% |
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)Alkylation of diethyl malonate (II) with 5-(4-chlorophenyl)pentyl bromide (I) gives diethyl 5-(4-chlorophenyl)pentyl malonate (III). Intermediate (III) is hydrolyzed to the monoester (IV), followed by condensation with paraformaldehyde in pyridine/piperidine to yield ethyl 7-(4-chlorophenyl)-2-methyleneheptanoate (V), which is oxidized with m-chloroperbenzoic acid. Alternatively, intermediate (IV) can be prepared by condensation of 4-chlorocinnamaldehyde (VI) with diethyl ethylidenemalonate (VII) to yield intermediate (VIII) and subsequent hydrogenation.
【1】 Eistetter, K.; Wolf, H.P.O.; Synthesis and hypoglycaemic activity of phenylalkyloxirane carboxylic acid derivatives. J Med Chem 1982, 25, 22, 109-113. |
【2】 Eistetter, K.; Rapp, E. (Byk Gulden Lomberg Chemische Fabrik GmbH); Substd. oxiranecarboxylic acids, their use and medicaments containing them. US 4324796 . |
【3】 Kohl, B.; Eistetter, K.; Amschler, H.; Ludwig, G.; Wolf, H.P.O. (Byk Gulden Lomberg Chemische Fabrik GmbH); Phenylalkyloxirane carboxylic acids, preparation and therapeutical use. EP 0071175 . |
【4】 Wolf, H.P.O.; Eistetter, K.; POCA. Drugs Fut 1983, 8, 5, 428. |
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) | 36082 | 1-(5-bromopentyl)-4-chlorobenzene | C11H14BrCl | 详情 | 详情 | |
(II) | 16829 | Diethyl malonate | 105-53-3 | C7H12O4 | 详情 | 详情 |
(III) | 36083 | diethyl 2-[5-(4-chlorophenyl)pentyl]malonate | C18H25ClO4 | 详情 | 详情 | |
(IV) | 36085 | 7-(4-chlorophenyl)-2-(ethoxycarbonyl)heptanoic acid | C16H21ClO4 | 详情 | 详情 | |
(V) | 35086 | 1-benzyl 4-(tert-butyl) (2R,3S)-2-isobutyl-3-(3-[[(4-nitrophenoxy)carbonyl]oxy]propyl)butanedioate | C29H37NO9 | 详情 | 详情 | |
(VI) | 36087 | (E)-3-(4-chlorophenyl)-2-propenal | C9H7ClO | 详情 | 详情 | |
(VII) | 36088 | (E)-2-(ethoxycarbonyl)-2-butenoic acid | C7H10O4 | 详情 | 详情 | |
(VIII) | 36084 | (2E,4E,6E)-7-(4-chlorophenyl)-2-(ethoxycarbonyl)-2,4,6-heptatrienoic acid | C16H15ClO4 | 详情 | 详情 |
Extended Information