1-(3-chloro-4-cyclohexylphenyl)-1-ethanone -Drug Synthesis Database

【结构式】

【分子编号】59241

【品名】1-(3-chloro-4-cyclohexylphenyl)-1-ethanone

【CA登记号】

【分子式】C₁₄H₁₇ClO

【分子量】236.74108

【元素组成】C 71.03% H 7.24% Cl 14.98% O 6.76%

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：(I)

Condensation of 3'-chloro-4'-cyclohexylacetophenone (I) with semicarbazide hydrochloride (II) produced the semicarbazone (III). Treatment of (III) with selenium dioxide in HOAc generated the intermediate selenodiazole (IV) which, on further heating, gave rise to the aryl acetylene (V). Cupric chloride-catalyzed Mannich condensation of acetylene (V) with N-ethyl cyclohexylamine (VI) and formaldehyde yielded the propargyl amine (VII). Partial hydrogenation of the triple bond of (VII) using the Lindlar catalyst provided the target (Z)-propenyl amine, which was finally converted to the hydrochloride salt.

参考文献中间体

合成目标

【1】 Breliere, J.-C.; Casellas, P.; Lavastre, S.; Paul, R. (Sanofi-Synthelabo); Benzene derivates, their preparation and pharmaceutical compsns. containing them. EP 0376850; FR 2641276; JP 1991002116; US 5354781 .

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)	59241	1-(3-chloro-4-cyclohexylphenyl)-1-ethanone		C₁₄H₁₇ClO	详情	详情
(II)	23944	1-Hydrazinecarboxamide	563-41-7	CH₅N₃O	详情	详情
(III)	59242	2-[(E)-1-(3-chloro-4-cyclohexylphenyl)ethylidene]-1-hydrazinecarboxamide		C₁₅H₂₀ClN₃O	详情	详情
(IV)	59243	4-(3-chloro-4-cyclohexylphenyl)-1,2,3-selenadiazole		C₁₄H₁₅ClN₂Se	详情	详情
(V)	59244	2-chloro-1-cyclohexyl-4-ethynylbenzene		C₁₄H₁₅Cl	详情	详情
(VI)	59245	N-Ethylcyclohexanamine; N-Ethylcyclohexylamine; Vulkacit HX	5459-93-8	C₈H₁₇N	详情	详情
(VII)	59246	N-[3-(3-chloro-4-cyclohexylphenyl)-2-propynyl]-N-cyclohexyl-N-ethylamine; N-[3-(3-chloro-4-cyclohexylphenyl)-2-propynyl]-N-ethylcyclohexanamine		C₂₃H₃₂ClN	详情	详情

Extended Information