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【结 构 式】 
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【分子编号】61076 【品名】6-(2-oxiranylmethoxy)tricyclo[6.2.2.0~2,7~]dodeca-2,4,6-trien-3-yl acetate 【CA登记号】 |
【 分 子 式 】C17H20O4 【 分 子 量 】288.3434 【元素组成】C 70.81% H 6.99% O 22.19% |
合成路线1
该中间体在本合成路线中的序号：(IX)The selective hydrolysis of 1,4-diacetoxy-5,6,7,8-tetrahydro-5,8-ethanonaphthalene (VII) with diethylamine in methanol gives 4-acetoxy-5,6,7,8-tetrahydro-5,8-ethano-1-naphthol (VIII), which is condensed with epichlorohydrin (III) by means of piperidine at 90 C to afford 1-acetoxy-4-(2,3-epoxypropoxy)-5,6,7,8-tetrahydro-5,8-ethanonaphthalene (VII). The reaction of (IX) with tert-butylamine (V) in refluxing toluene gives 1-acetoxy-4-[3-(tert-butylamino)-2-hydroxypropoxy]-5,6,7,8-tetrahydro-5,8-ethanonaphthalene (X), which is finally hydrolyzed with dry HCl in refluxing methanol
| 【1】 Lauria, F.; et al. (Carlo Erba, S.p.A.); BE 790188; CA 992983; CH 565741; DE 2251095; FR 2157897; GB 1351557; JP 7349750; NL 7214106; ZA 7207459 . |
| 【2】 Blancafort, P.; Serradell, M.N.; Castaner, J.; McGillion, F.B.; Nafetolol. Drugs Fut 1981, 6, 2, 92. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (III) | 10146 | Epichlorohydrin; 2-(Chloromethyl)oxirane | 106-89-8 | C3H5ClO | 详情 | 详情 |
| (V) | 17895 | 2-Amino-2-methylpropane; tert-butylamine; 2-methyl-2-propanamine | 75-64-9 | C4H11N | 详情 | 详情 |
| (VII) | 61074 | 6-(acetyloxy)tricyclo[6.2.2.0~2,7~]dodeca-2,4,6-trien-3-yl acetate | C16H18O4 | 详情 | 详情 | |
| (VIII) | 61075 | 6-hydroxytricyclo[6.2.2.0~2,7~]dodeca-2,4,6-trien-3-yl acetate | C14H16O3 | 详情 | 详情 | |
| (IX) | 61076 | 6-(2-oxiranylmethoxy)tricyclo[6.2.2.0~2,7~]dodeca-2,4,6-trien-3-yl acetate | C17H20O4 | 详情 | 详情 | |
| (X) | 61077 | 6-[3-(tert-butylamino)-2-hydroxypropoxy]tricyclo[6.2.2.0~2,7~]dodeca-2,4,6-trien-3-yl acetate | C21H31NO4 | 详情 | 详情 |