1-(2-trimethylsilylethynylcyclopent-1-enyl)-3-trimethylsilylbuta-1,2-dienyl acetate | 915378-33-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-(2-trimethylsilylethynylcyclopent-1-enyl)-3-trimethylsilylbuta-1,2-dienyl acetate
• CAS: 915378-33-5
• 化学式: C₁₉H₃₀O₂Si₂
• 分子量: 346.617
• InChiKey: WMXASSOTQHPLNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.22
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-trimethylsilylethynylcyclopent-1-enyl)-3-trimethylsilylbuta-1,2-dienyl acetate 在 1,4-环己二烯 、 甲基锂 作用下， 以 乙醚 、 苯 为溶剂， 反应 5.0h， 以34%的产率得到1-(2-trimethylsilylethynylcyclopent-1-enyl)-3-trimethylsilylbut-2-en-1-one
  参考文献：
  名称：

  Ring Size and Substituent Effects in Oxyanion-Promoted Cyclizations of Enyne-allenes:  Observation of a Myers−Saito Cycloaromatization at Cryogenic Temperature

  摘要：

  A series of acetoxy-substituted enyne-allenes, fused to cyclopentene and cyclohexene ring systems, were synthesized and treated with methyllithium to generate the corresponding enolates. It was found that whereas the cyclohexannulated examples underwent either C-2-C-7 (Myers-Saito) cycloaromatization or C-2-C-6 (Schmittel) cyclization depending on their terminal subsituents, the cyclopentannulated examples either failed to cyclize altogether or underwent C-2-C-7 cyclization. Both of these results lie in contrast to the behavior of their benzannulated analogues, which underwent exclusive C-2-C-6 cyclization independent of substituents. These findings are rationalized on the basis of both ring strain effects and the steric encumbrance of the terminal alkynyl and allenyl subsituents.

  DOI：

  10.1021/jo061088n
• 作为产物：
  描述：

  1-(2-trimethylsilylacetylenylcyclopent-1-enyl)-3-trimethylsilylpropyn-1-one 、 甲基锂 、 乙酸酐 在 copper(l) iodide 作用下， 以 乙醚 为溶剂， 反应 2.08h， 以44%的产率得到1-(2-trimethylsilylethynylcyclopent-1-enyl)-3-trimethylsilylbuta-1,2-dienyl acetate
  参考文献：
  名称：

  Ring Size and Substituent Effects in Oxyanion-Promoted Cyclizations of Enyne-allenes:  Observation of a Myers−Saito Cycloaromatization at Cryogenic Temperature

  摘要：

  A series of acetoxy-substituted enyne-allenes, fused to cyclopentene and cyclohexene ring systems, were synthesized and treated with methyllithium to generate the corresponding enolates. It was found that whereas the cyclohexannulated examples underwent either C-2-C-7 (Myers-Saito) cycloaromatization or C-2-C-6 (Schmittel) cyclization depending on their terminal subsituents, the cyclopentannulated examples either failed to cyclize altogether or underwent C-2-C-7 cyclization. Both of these results lie in contrast to the behavior of their benzannulated analogues, which underwent exclusive C-2-C-6 cyclization independent of substituents. These findings are rationalized on the basis of both ring strain effects and the steric encumbrance of the terminal alkynyl and allenyl subsituents.

  DOI：

  10.1021/jo061088n