1-hepten-3-one -Drug Synthesis Database

【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.

参考文献中间体

合成目标

【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