(R)-2-bromo-1<(tert-butyldiphenylsilyl)oxy>-3-butyne | 131905-88-9

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (R)-2-bromo-1<(tert-butyldiphenylsilyl)oxy>-3-butyne
• 英文别名: 2-Bromobut-3-ynoxy-tert-butyl-diphenylsilane
• CAS: 131905-88-9
• 化学式: C₂₀H₂₃BrOSi
• 分子量: 387.392
• InChiKey: JXWISLMOTYYBDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  叔丁基二苯基氯硅烷 在 吡啶 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 4.75h， 生成 (R)-2-bromo-1<(tert-butyldiphenylsilyl)oxy>-3-butyne
  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

文献信息

• Enantioselective formation of functionalized 1,3-disubstituted allenes: synthesis of .alpha.-allenic .omega.-carbomethoxy alcohols of high optical purity
  作者：Owen W. Gooding、Colin C. Beard、David Y. Jackson、Douglas L. Wren、Gary F. Cooper

  DOI：10.1021/jo00003a033

  日期：1991.2

  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.