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【结 构 式】 
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【分子编号】40132 【品名】3-(5H-dibenzo[a,d]cyclohepten-5-ylidene)propyl 4-methylbenzenesulfonate 【CA登记号】 |
【 分 子 式 】C25H22O3S 【 分 子 量 】402.51388 【元素组成】C 74.6% H 5.51% O 11.92% S 7.97% |
合成路线1
该中间体在本合成路线中的序号：(VIII)The Grignard reaction of dibenzo[a,d]cyclohepta-1,4,6-triene-5-one (I) with cyclopropyl magnesium bromide (D) in THF gives 5-hydroxy-5-cyclopropyldibenzo[a,d]cyclohepta-1,4,6-triene (V), which is then treated with HBr in acetic acid to yield 5-(3-bromopropylidene)dibenzo[a,d]cyclohepta-1,4,6-triene (VI). Finally, (VI) is treated with dimethylamine (B) in benzene at 95 C. The hydroxycompound (V), obtained as before, is treated with HClO4 in dioxane to yield 5-(3-hydroxypropylidene)dibenzo[a,d]cyclohepta-1,4,6-triene (VII), which is then treated with p-toluenesulfonyl chloride in pyridine to afford the tosyl derivate (VIII). Finally, (VIII) is treated with dimethylamine (B) in benzene at 100 C.
| 【1】 Roberts, P.J.; Castañer, J.; Cyclobenzaprine. Drugs Fut 1977, 2, 5, 299. |
| 【2】 Hoffsommer, R.D. Jr.; et al.; Nouveaux derives de dibenzocycloheptenes et leur preparation. BE 0631012 . |
| 【3】 Wendler, N.L.; Dibenzocycloheptenes. BE 0633316 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (D) | 12450 | Bromo(cyclopropyl)magnesium;cyclopropylmagnesium bromide;cyclopropylmagnesiumbromide | 23719-80-4 | C3H5BrMg | 详情 | 详情 |
| (B) | 19443 | N-methylmethanamine; N,N-dimethylamine | 124-40-3 | C2H7N | 详情 | 详情 |
| (I) | 29151 | 5H-dibenzo[a,d]cyclohepten-5-one; Dibenzosuberenone | 2222-33-5 | C15H10O | 详情 | 详情 |
| (V) | 40129 | 5-cyclopropyl-5H-dibenzo[a,d]cyclohepten-5-ol | C18H16O | 详情 | 详情 | |
| (VI) | 40130 | 5-(3-bromopropylidene)-5H-dibenzo[a,d]cycloheptene | C18H15Br | 详情 | 详情 | |
| (VII) | 40131 | 3-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-propanol | C18H16O | 详情 | 详情 | |
| (VIII) | 40132 | 3-(5H-dibenzo[a,d]cyclohepten-5-ylidene)propyl 4-methylbenzenesulfonate | C25H22O3S | 详情 | 详情 |