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【结 构 式】 
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【分子编号】36028 【品名】(E)-1-butyl-4-(tributylstannyl)-1-vinyl-3-butenyl trimethylsilyl ether; [[(E)-1-butyl-4-(tributylstannyl)-1-vinyl-3-butenyl]oxy](trimethyl)silane 【CA登记号】 |
【 分 子 式 】C25H52OSiSn 【 分 子 量 】515.48278 【元素组成】C 58.25% H 10.17% O 3.1% Si 5.45% Sn 23.03% |
合成路线1
该中间体在本合成路线中的序号：(XVII)The oxidation of 1-hepten-3-ol (XII) with pyridinium chlorochromate gives 1-hepten-3-one (XIII), which by a Grignard condensation with propargylmagnesium bromide (XIV) is converted into 4-hydroxy-4-vinyl-1-octyne (XV). The protection of (XV) with trimethylsilyl chloride and imidazole in DMF yields 4-trimethylsilyloxy-4-vinyl-1-octyne (XVI), which by reaction with tri-n-butyl-stannane and azobisisobutyronitrile at 125 C affords 1-(tri-n-butylstannyl)-4-vinyl-4-(trimethylsilyloxy)-1-octene (XVII). Finally, this compound by reaction with butyllithium and copper -1-pentyne-tributylphosphine (C) in HMPT yields the copper salt (VIII), already obtained.
| 【1】 Grudzinkas, C.V.; Bimbaum, J.E.; Chen. S.L.; Chan, P.S.; Floyd, M.B.; Weiss, M.J.; Cervoni, P.; Prostaglandins and congeners. 29. (16RS)-Rac-15-deoxy-16-hydroxy-16-vivyl-protaglandin E2, an orally and transdermally active hypotensive agent of prolonged duration. J Med Chem 1982, 25, 5, 492-494. |
| 【2】 Hillier, K.; Blancafort, P.; Serradell, M.N.; Castaner, J.; CL-115,347. Drugs Fut 1983, 8, 4, 307. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VIII) | 36021 | [(1E)-4-butyl-4-[(trimethylsilyl)oxy]-1,5-hexadienyl](1-pentynyl)copper | C18H32CuOSi | 详情 | 详情 | |
| (XII) | 36025 | 1-hepten-3-ol | 4938-52-7 | C7H14O | 详情 | 详情 |
| (XIII) | 36026 | 1-hepten-3-one | C7H12O | 详情 | 详情 | |
| (XIV) | 29064 | bromo(2-propynyl)magnesium | C3H3BrMg | 详情 | 详情 | |
| (XV) | 29325 | 3-butyl-1-hexen-5-yn-3-ol | C10H16O | 详情 | 详情 | |
| (XVI) | 36027 | 1-butyl-1-vinyl-3-butynyl trimethylsilyl ether; [(1-butyl-1-vinyl-3-butynyl)oxy](trimethyl)silane | C13H24OSi | 详情 | 详情 | |
| (XVII) | 36028 | (E)-1-butyl-4-(tributylstannyl)-1-vinyl-3-butenyl trimethylsilyl ether; [[(E)-1-butyl-4-(tributylstannyl)-1-vinyl-3-butenyl]oxy](trimethyl)silane | C25H52OSiSn | 详情 | 详情 | |
| (C) | 29069 | 1-pentynylcopper | C5H7Cu | 详情 | 详情 |