【结 构 式】 |
【分子编号】53908 【品名】3-Methoxy-2-cyclohexen-1-one 【CA登记号】16807-60-6 |
【 分 子 式 】C7H10O2 【 分 子 量 】126.1552 【元素组成】C 66.65% H 7.99% O 25.36% |
合成路线1
该中间体在本合成路线中的序号:(I)Treatment of 3-methoxy-2-cyclohexen-1-one (I) with n-butyllithium and diisopropylamine in THF, followed by addition of N,N-dimethylmethylene ammonium iodide (Eschenmoser's salt) (II) and precipitation with maleic acid, furnishes maleate (III). Methylation of (III) with iodomethane in DMF, followed by condensation with 2-methylimidazole (IV), affords compound (V), which is then converted into methylphenyl hydrazino derivative (VII) by first treatment with HCl in H2O followed by reaction with 1-methyl-1-phenylhydrazine (VI). Cyclization of (VII) is then performed by means of ZnCl2 in HOAc at 85 C to give carbazolone (VIII), and finally the target product is obtained by formation of the hydrochloride dihydrate salt.
【1】 Bell, J.A.; Ewan, G.B.; Oxford, A.W.; Humber, D.C.; Eldred, C.D.; Costes, I.H. (GlaxoSmithKline plc); Process for the preparation of 3-imidazolylmethyltetrahydrocarbazolones. EP 0219929 . |
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) | 53908 | 3-Methoxy-2-cyclohexen-1-one | 16807-60-6 | C7H10O2 | 详情 | 详情 |
(II) | 48555 | Eschenmoser's salt; N,N-Dimethylmethyleneimmonium chloride; N,N-Dimethylmethyleneimmonium iodide | C3H8IN | 详情 | 详情 | |
(III) | 55373 | C14H21NO6 | 详情 | 详情 | ||
(IV) | 15670 | 2-Methylimidazole; 2-Methyl-1H-imidazole | 693-98-1 | C4H6N2 | 详情 | 详情 |
(V) | 53910 | 3-methoxy-6-[(2-methyl-1H-imidazol-1-yl)methyl]-2-cyclohexen-1-one | C12H16N2O2 | 详情 | 详情 | |
(VI) | 53911 | 1-Methyl-1-phenylhydrazine; 1-Methylphenylhydrazine | 618-40-6 | C7H10N2 | 详情 | 详情 |
(VII) | 53912 | 6-[(2-methyl-1H-imidazol-1-yl)methyl]-3-(2-methyl-2-phenylhydrazino)-2-cyclohexen-1-one | n/a | C18H22N4O | 详情 | 详情 |
(VIII) | 53903 | 9-methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-1,2,3,9-tetrahydro-4H-carbazol-4-one | n/a | C18H19N3O | 详情 | 详情 |