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【结 构 式】 
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【分子编号】12584 【品名】2-(2-Hydroxyethyl)-6,11-dihydrodibenzo[b,e]oxepin-11-ol 【CA登记号】 |
【 分 子 式 】C16H16O3 【 分 子 量 】256.30124 【元素组成】C 74.98% H 6.29% O 18.73% |
合成路线1
该中间体在本合成路线中的序号：(X)Reduction of 11-oxo-6,11-dihydrodibenz[b,e]oxepin-2-acetic acid methyl ester (IV) with lithium aluminum hydride gives 11-hydroxy-2-(2-hydroxyethyl)-6,11-dihydrodibenz[b,e]oxepin (X), whose primary hydroxyl group is protected with triphenylchloromethane in pyridine to yield 11-hydroxy-2-(2-triphenylmethoxyethyl)-6,11-dihdrodibenz[b,e]oxepin (XI). Oxidation of (XI) with potassium permanganate affords 11-oxo-2-(2-triphenylmethoxyethyl)-6,11-dihydrodibenz[b,e]oxepin (XII), which is treated with 3-(dimethylamino)propylmagnesium chloride (XIII) to give 11-[3-(dimethylamino)propyl]-11-hydroxy-2-(2-triphenylmethoxyethyl)-6,11-dihydrodibenz[b,e]oxepin (XIV). Elimation of water with phosphorous oxychloride yields 11-[3-(dimethylamino)propylidene]-2-(2-triphenylmethoxyethyl)-6,11-dihydrodibenz[b,e]oxepin (XV), which is deprotected with p-toluenesulfonic acid to 11-[3-(dimethylamino)propylidene]- 2-(2-hydroxyethyl)-6,11-dihydrodibenz[b,e]oxepin (XVI). Finally, compound (XVI) is oxidized with Jones reagent.
| 【1】 Iwao, J.; Iso, T.; Oya, M. (Santen Pharmaceutical Co., Ltd.); Novel benzothiazine derivs.. EP 0237573; JP 1987123181; US 4786635; WO 8700838 . |
| 【2】 Oshiam, E.; Kumazawa, T.; Otaki, S.; Obase, H.; Ohmori, K.; Ishii, H.; Manabe, H.; Tamura, T.; Shuto, K. (Kyowa Hakko Kogyo Co., Ltd.); Dibenz[b,e]oxepin deriv. and antiallergic and antiinflammatory agent. EP 0235796; JP 1988010784; US 5116863 . |
| 【3】 Iwao, J.; Iso, T.; Kawashima, Y. (Santen Pharmaceutical Co., Ltd.); Sulfur-containing polycyclic cpds. JP 1988104969 . |
| 【4】 Prous, J.; Castaner, J.; Graul, A.; KW-4679. Drugs Fut 1993, 18, 9, 794. |
| 【5】 Yamauchi, H.; Kawashima, Y.; Yamamoto, K.; Ito, S.; Iwao, J.-I.; Fujita, M.; Ota, A.; Kato, N.; Synthesis and Ca2+ antagonistic activity of 2-[2-[(aminoalkyl)oxy]-5-methoxyphenyl]-3,4-dihydro-4-methyl-3-oxo-2H -1,4-benzothiazines. J Med Chem 1990, 33, 7, 1898-905. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (X) | 12584 | 2-(2-Hydroxyethyl)-6,11-dihydrodibenzo[b,e]oxepin-11-ol | C16H16O3 | 详情 | 详情 | |
| (XI) | 12585 | 2-[2-(Trityloxy)ethyl]-6,11-dihydrodibenzo[b,e]oxepin-11-ol | C35H30O3 | 详情 | 详情 | |
| (XII) | 12586 | 2-[2-(Trityloxy)ethyl]dibenzo[b,e]oxepin-11(6H)-one | C35H28O3 | 详情 | 详情 | |
| (XIII) | 12587 | Chloro[3-(dimethylamino)propyl]magnesium | C5H12ClMgN | 详情 | 详情 | |
| (XIV) | 12588 | 11-[3-(Dimethylamino)propyl]-2-[2-(trityloxy)ethyl]-6,11-dihydrodibenzo[b,e]oxepin-11-ol | C40H41NO3 | 详情 | 详情 | |
| (XV) | 12589 | N,N-Dimethyl-N-[3-[2-[2-(trityloxy)ethyl]dibenzo[b,e]oxepin-11(6H)-ylidene]propyl]amine; N,N-Dimethyl-3-[2-[2-(trityloxy)ethyl]dibenzo[b,e]oxepin-11(6H)-ylidene]-1-propanamine | C40H39NO2 | 详情 | 详情 | |
| (XVI) | 12590 | 2-[11-[(Z)-3-(Dimethylamino)propylidene]dibenzo[b,e]oxepin-2(6H)-yl]-1-ethanol | C21H25NO2 | 详情 | 详情 |