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【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
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