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【结 构 式】 
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【分子编号】59390 【品名】6-[bis(4-methoxyphenyl)methyl]-9-bromo-12-(3-hydroxypropyl)-6,7,12,13-tetrahydro-5H-indeno[2,1-a]pyrrolo[3,4-c]carbazol-5-one 【CA登记号】 |
【 分 子 式 】C39H33BrN2O4 【 分 子 量 】673.6061 【元素组成】C 69.54% H 4.94% Br 11.86% N 4.16% O 9.5% |
合成路线1
该中间体在本合成路线中的序号：(VI)Michael addition of ethyl acrylate (II) to the indenopyrrolocarbazole (I) provided (III). Lactam N-protection of (III) with dimethoxybenzhydrol yielded N-protected ethyl ester (IV), which was reduced with LiBH4 to give alcohol (V). Subsequent bromination of (V) with N-bromosuccinimide yielded (VI), which was first submitted to palladium-catalyzed carbonylation in methoxyethanol and then N-deprotected with trifluoroacetic acid and thioanisole to furnish (VII). Finally, reduction of ester (VII) with DIBAL furnished the diol intermediate (VIII).
| 【1】 Hudkins, R.L.; Gingrich, D.E. (Cephalon, Inc.); Selected fused pyrrolocarbazoles. WO 0217914 . |
| 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) | 59386 | 6,7,12,13-tetrahydro-5H-indeno[2,1-a]pyrrolo[3,4-c]carbazol-5-one | C21H14N2O | 详情 | 详情 | |
| (II) | 10164 | ethyl acrylate | 140-88-5 | C5H8O2 | 详情 | 详情 |
| (III) | 59387 | ethyl 3-(5-oxo-5,6,7,13-tetrahydro-12H-indeno[2,1-a]pyrrolo[3,4-c]carbazol-12-yl)propanoate | C26H22N2O3 | 详情 | 详情 | |
| (IV) | 59388 | ethyl 3-{6-[bis(4-methoxyphenyl)methyl]-5-oxo-5,6,7,13-tetrahydro-12H-indeno[2,1-a]pyrrolo[3,4-c]carbazol-12-yl}propanoate | C41H36N2O5 | 详情 | 详情 | |
| (V) | 59389 | 6-[bis(4-methoxyphenyl)methyl]-12-(3-hydroxypropyl)-6,7,12,13-tetrahydro-5H-indeno[2,1-a]pyrrolo[3,4-c]carbazol-5-one | C39H34N2O4 | 详情 | 详情 | |
| (VI) | 59390 | 6-[bis(4-methoxyphenyl)methyl]-9-bromo-12-(3-hydroxypropyl)-6,7,12,13-tetrahydro-5H-indeno[2,1-a]pyrrolo[3,4-c]carbazol-5-one | C39H33BrN2O4 | 详情 | 详情 | |
| (VII) | 59391 | 2-methoxyethyl 12-(3-hydroxypropyl)-5-oxo-6,7,12,13-tetrahydro-5H-indeno[2,1-a]pyrrolo[3,4-c]carbazole-9-carboxylate | C28H26N2O5 | 详情 | 详情 | |
| (VIII) | 59392 | 9-(hydroxymethyl)-12-(3-hydroxypropyl)-6,7,12,13-tetrahydro-5H-indeno[2,1-a]pyrrolo[3,4-c]carbazol-5-one | C25H22N2O3 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(VI)Michael addition of ethyl acrylate (II) to the indenopyrrolocarbazole (I) provided (III). Lactam N-protection of (III) with dimethoxybenzhydrol yielded N-protected ethyl ester (IV), which was reduced with LiBH4 to give alcohol (V). Subsequent bromination of (V) with N-bromosuccinimide yielded (VI), which was first submitted to palladium-catalyzed carbonylation in methoxyethanol and then N-deprotected with trifluoroacetic acid and thioanisole to furnish (VII). Finally, reduction of ester (VII) with DIBAL furnished the diol intermediate (VIII).
| 【1】 Hudkins, R.L.; Gingrich, D.E. (Cephalon, Inc.); Selected fused pyrrolocarbazoles. WO 0217914 . |
| 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) | 59386 | 6,7,12,13-tetrahydro-5H-indeno[2,1-a]pyrrolo[3,4-c]carbazol-5-one | C21H14N2O | 详情 | 详情 | |
| (II) | 10164 | ethyl acrylate | 140-88-5 | C5H8O2 | 详情 | 详情 |
| (III) | 59387 | ethyl 3-(5-oxo-5,6,7,13-tetrahydro-12H-indeno[2,1-a]pyrrolo[3,4-c]carbazol-12-yl)propanoate | C26H22N2O3 | 详情 | 详情 | |
| (IV) | 59388 | ethyl 3-{6-[bis(4-methoxyphenyl)methyl]-5-oxo-5,6,7,13-tetrahydro-12H-indeno[2,1-a]pyrrolo[3,4-c]carbazol-12-yl}propanoate | C41H36N2O5 | 详情 | 详情 | |
| (V) | 59389 | 6-[bis(4-methoxyphenyl)methyl]-12-(3-hydroxypropyl)-6,7,12,13-tetrahydro-5H-indeno[2,1-a]pyrrolo[3,4-c]carbazol-5-one | C39H34N2O4 | 详情 | 详情 | |
| (VI) | 59390 | 6-[bis(4-methoxyphenyl)methyl]-9-bromo-12-(3-hydroxypropyl)-6,7,12,13-tetrahydro-5H-indeno[2,1-a]pyrrolo[3,4-c]carbazol-5-one | C39H33BrN2O4 | 详情 | 详情 | |
| (VII) | 59391 | 2-methoxyethyl 12-(3-hydroxypropyl)-5-oxo-6,7,12,13-tetrahydro-5H-indeno[2,1-a]pyrrolo[3,4-c]carbazole-9-carboxylate | C28H26N2O5 | 详情 | 详情 | |
| (VIII) | 59392 | 9-(hydroxymethyl)-12-(3-hydroxypropyl)-6,7,12,13-tetrahydro-5H-indeno[2,1-a]pyrrolo[3,4-c]carbazol-5-one | C25H22N2O3 | 详情 | 详情 |