7-(tert-Butyl-diphenyl-silanyloxy)-hepta-4,5-dienoic acid methyl ester | 131905-95-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 7-(tert-Butyl-diphenyl-silanyloxy)-hepta-4,5-dienoic acid methyl ester
• CAS: 131905-95-8
• 化学式: C₂₄H₃₀O₃Si
• 分子量: 394.586
• InChiKey: KWTVDSFEERCINO-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.23
• 重原子数：
  28.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  7-(tert-Butyl-diphenyl-silanyloxy)-hepta-4,5-dienoic acid methyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以93%的产率得到(R)-(-)-methyl 7-hydroxy-4,5-heptadienoate
  参考文献：
  名称：

  Enantioselective formation of functionalized 1,3-disubstituted allenes: synthesis of .alpha.-allenic .omega.-carbomethoxy alcohols of high optical purity

  摘要：

  A general, high yield synthesis of multigram quantities of the title allenic alcohols is described. Intermediate 5, derived from D-mannitol, was elaborated to both enantiomers (10 and 11) of the antifungal constituent (11) of Sapium japonicum and the lower homologue (16) useful for the synthesis of allenyl prostaglandins. The natural material was thus shown to possess the R configuration. The product allenes were formed in > 94% ee as determined by C-13 NMR spectral analysis of the corresponding Mosher esters.

  DOI：

  10.1021/jo00003a033
• 作为产物：
  描述：

  、 (R)-2-bromo-1<(tert-butyldiphenylsilyl)oxy>-3-butyne 在 N,N-二甲基丙烯基脲 作用下， 以 甲苯 为溶剂， 反应 0.25h， 以85.3%的产率得到7-(tert-Butyl-diphenyl-silanyloxy)-hepta-4,5-dienoic acid methyl ester
  参考文献：
  名称：

  Enantioselective formation of functionalized 1,3-disubstituted allenes: synthesis of .alpha.-allenic .omega.-carbomethoxy alcohols of high optical purity

  摘要：

  A general, high yield synthesis of multigram quantities of the title allenic alcohols is described. Intermediate 5, derived from D-mannitol, was elaborated to both enantiomers (10 and 11) of the antifungal constituent (11) of Sapium japonicum and the lower homologue (16) useful for the synthesis of allenyl prostaglandins. The natural material was thus shown to possess the R configuration. The product allenes were formed in > 94% ee as determined by C-13 NMR spectral analysis of the corresponding Mosher esters.

  DOI：

  10.1021/jo00003a033