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【结 构 式】 
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【分子编号】30654 【品名】3,8-chromanediol 【CA登记号】 |
【 分 子 式 】C9H10O3 【 分 子 量 】166.1766 【元素组成】C 65.05% H 6.07% O 28.88% |
合成路线1
该中间体在本合成路线中的序号：(I)The reaction of 3,4-dihydro-2H-1-benzopyran-3,8-diol (I) with ethyl chloroformate by means of triethylamine in THF gives 3,4-dihydro-8-lethoxy carbonyloxyl-2H-1-benzopyran-3-ol (II), which is treated with nitric acid and acetic anhydride in acetonitrile to yield 3,4-dihydro-8-(ethoxycarbonyloxy)-2H-1-benzopyran-3-ol-3-nitrate (III). The hydrolysis of (III) with NaOH in methanol affords 3,4-dihydro-8-hydroxy-2H-1-benzopyran-3-ol 3-nitrate (IV), which is condensed with epichlorohydrin (V) by means of NaOH in water giving 3,4-dihydro-8-(2,3-epoxypropoxy)-2H-1-benzopyran-3-ol 3-nitrate (VI). Finally, this compound is treated with isopropylamine in refluxing ethanol.
| 【1】 Shiratsuohi, M.; Shimizu, N.; Shigyo, H.; Kyotani, Y.; Kunieda, H.; Kawamura, K.; Sato, S.; Akashi, T.; Nagakura, M. (Kowa Co., Ltd.); Dihydrobenzopyran compounds and pharmaceutical composition comprising said compounds. EP 0042299; JP 57007481; JP 82106619 . |
| 【2】 Blancafort, P.; Thorpe, P.J.; Serradell, M.N.; Castaner, J.; K-351. Drugs Fut 1983, 8, 6, 497. |
| 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) | 30654 | 3,8-chromanediol | C9H10O3 | 详情 | 详情 | |
| (II) | 30655 | ethyl 3-hydroxy-3,4-dihydro-2H-chromen-8-yl carbonate | C12H14O5 | 详情 | 详情 | |
| (III) | 30656 | ethyl 3-(nitrooxy)-3,4-dihydro-2H-chromen-8-yl carbonate | C12H13NO7 | 详情 | 详情 | |
| (IV) | 30657 | 3-(nitrooxy)-8-chromanol | C9H9NO5 | 详情 | 详情 | |
| (V) | 10146 | Epichlorohydrin; 2-(Chloromethyl)oxirane | 106-89-8 | C3H5ClO | 详情 | 详情 |
| (VI) | 30658 | 3-(nitrooxy)-3,4-dihydro-2H-chromen-8-yl 2-oxiranylmethyl ether; 3-(nitrooxy)-8-(2-oxiranylmethoxy)chromane | C12H13NO6 | 详情 | 详情 | |
| (VII) | 23933 | 2-Propanamine; Isopropylamine | 75-31-0 | C3H9N | 详情 | 详情 |