(2E,4E,6E)-7-(4-chlorophenyl)-2-(ethoxycarbonyl)-2,4,6-heptatrienoic acid -Drug Synthesis Database

【结构式】

【分子编号】36084

【品名】(2E,4E,6E)-7-(4-chlorophenyl)-2-(ethoxycarbonyl)-2,4,6-heptatrienoic acid

【CA登记号】

【分子式】C₁₆H₁₅ClO₄

【分子量】306.7454

【元素组成】C 62.65% H 4.93% Cl 11.56% O 20.86%

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：(VIII)

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.

参考文献中间体

合成目标

【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