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【结 构 式】 
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【分子编号】59242 【品名】2-[(E)-1-(3-chloro-4-cyclohexylphenyl)ethylidene]-1-hydrazinecarboxamide 【CA登记号】 |
【 分 子 式 】C15H20ClN3O 【 分 子 量 】293.79612 【元素组成】C 61.32% H 6.86% Cl 12.07% N 14.3% O 5.45% |
合成路线1
该中间体在本合成路线中的序号：(III)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.
| 【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 |