【结 构 式】 |
【分子编号】57088 【品名】4-amino-4-phenylcyclohexanone 【CA登记号】 |
【 分 子 式 】C12H15NO 【 分 子 量 】189.25724 【元素组成】C 76.16% H 7.99% N 7.4% O 8.45% |
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:(XII)Michael addition of methyl acrylate (VIII) to methyl phenylacetate (VII) in the presence of NaH produces the intermediate triester (IX) which, under the reaction conditions, undergoes Dieckmann cyclization to the cyclohexanone diester (X). Hydrolysis and decarboxylation of keto diester (X) leads to keto acid (XI). This is then subjected to Curtius rearrangement in the presence of diphenylphosphoryl azide (DPPA) to yield, after acidic hydrolysis of the intermediate isocyanate, the amino cyclohexanone (XII). Acylation of amine (XII) by acid chloride (VI) then gives amide (XIII).
【1】 Elliott, J.M.; Castro Pineiro, J.L.; Swain, C.J.; Hollingworth, G.J.; Dinnell, K.; Shaw, D.E. (Merck Sharp & Dohme Ltd.); Cyclohexane derivs. and their use as therapeutic agents. WO 0187838 . |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(VI) | 57084 | 2-[3,5-bis(trifluoromethyl)phenyl]propanoyl chloride | C11H7ClF6O | 详情 | 详情 | |
(VII) | 32831 | methyl 2-phenylacetate | 101-41-7 | C9H10O2 | 详情 | 详情 |
(VIII) | 14156 | methyl acrylate | 96-33-3 | C4H6O2 | 详情 | 详情 |
(IX) | 57085 | trimethyl 3-phenyl-1,3,5-pentanetricarboxylate | C17H22O6 | 详情 | 详情 | |
(X) | 57086 | dimethyl 4-oxo-1-phenyl-1,3-cyclohexanedicarboxylate | C16H18O5 | 详情 | 详情 | |
(XI) | 57087 | 4-oxo-1-phenylcyclohexanecarboxylic acid | C13H14O3 | 详情 | 详情 | |
(XII) | 57088 | 4-amino-4-phenylcyclohexanone | C12H15NO | 详情 | 详情 | |
(XIII) | 57089 | 2-[3,5-bis(trifluoromethyl)phenyl]-N-(4-oxo-1-phenylcyclohexyl)propanamide | C23H21F6NO2 | 详情 | 详情 |
Extended Information