【结 构 式】 |
【分子编号】34263 【品名】1-cyclohexyl-1-ethanone 【CA登记号】823-76-7 |
【 分 子 式 】C8H14O 【 分 子 量 】126.19856 【元素组成】C 76.14% H 11.18% O 12.68% |
合成路线1
该中间体在本合成路线中的序号:(V)Mannich reaction of acetylcyclohexane (V), paraformaldehyde and 1-norephedrine (I) in the presence of hydrochloric acid yields alifedrine hydrochloride. Mannich reaction of 1-acetylcyclohexene (VI) with paraformaldehyde and (I) followed by catalytic hydrogenation of the resulting beta-aminoketone (III) also gives alifedrine hydrochloride.
【1】 Engel, J.; et al.; Cycloaliphatic ketoamines. DE 2919495; FR 2426040; GB 2023575; JP 54151950; US 4542159 . |
【2】 Bahre, M.; Thiemer, K.; Engel, J.; Breuel, H.P.; Stroman, F.; Kleemann, A.; Alifedrine. Drugs Fut 1984, 9, 10, 727. |
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) | 34264 | 2-amino-1-phenyl-1-propanol | C9H13NO | 详情 | 详情 | |
(II) | 34261 | 1-(1-cyclohexen-1-yl)-3-[(2-hydroxy-1-methyl-2-phenylethyl)amino]-1-propanone | C18H25NO2 | 详情 | 详情 | |
(III) | 34262 | 4-methyl-3-[(4-methyl-5-phenyl-1,3-oxazolidin-3-yl)methyl]-5-phenyl-1,3-oxazolidine | C21H26N2O2 | 详情 | 详情 | |
(V) | 34263 | 1-cyclohexyl-1-ethanone | 823-76-7 | C8H14O | 详情 | 详情 |
(VI) | 34260 | 1-(1-cyclohexen-1-yl)-1-ethanone | 932-66-1 | C8H12O | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号:(V)For [14C]-labelling of alifedrine, the following reaction sequence has been used: In the first step Friedel-Crafts'-like acylation of ethylene (A) with cyclohexanoyl chloride (VII) in the presence of aluminum chloride yields beta-chloroethylcyclohexyl ketone (VIII), which reacts with (I) to give alifedrine hydrochloride. Alifedrine has also been synthesized by catalytic hydrogenation of (V) with 1-norephedrine (I) in the presence of hydrochloric acid and paraformaldehyde.
【1】 Engel, J.; et al.; Novel cycloaliphatic enamines. DE 3213371 . |
【2】 Engel, J.; et al.; Cycloaliphatic ketoamines. DE 2919495; FR 2426040; GB 2023575; JP 54151950; US 4542159 . |
【3】 Klingler, K.G.; Engel, J.; Bickel, E.; Syntheses of 14C-1-erythro-norephedrine and its N-substitution products 14C-oxyfedrine and 14C-D 13,625. Arzneim-Forsch Drug Res 1983, 33, 9, 1213. |
【4】 Bahre, M.; Thiemer, K.; Engel, J.; Breuel, H.P.; Stroman, F.; Kleemann, A.; Alifedrine. Drugs Fut 1984, 9, 10, 727. |
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) | 34264 | 2-amino-1-phenyl-1-propanol | C9H13NO | 详情 | 详情 | |
(V) | 34263 | 1-cyclohexyl-1-ethanone | 823-76-7 | C8H14O | 详情 | 详情 |
(VII) | 17220 | cyclohexanecarbonyl chloride; Cyclohexanecarboxylic acid chloride | 2719-27-9 | C7H11ClO | 详情 | 详情 |
(VIII) | 34265 | 3-chloro-1-cyclohexyl-1-propanone | C9H15ClO | 详情 | 详情 |