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【结 构 式】

【分子编号】36026

【品名】1-hepten-3-one

【CA登记号】

【 分 子 式 】C7H12O

【 分 子 量 】112.17168

【元素组成】C 74.95% H 10.78% O 14.26%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(XIII)

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
Extended Information