1-(2-trimethylsilylacetylenylcyclopent-1-enyl)-3-trimethylsilylpropyn-1-one | 915378-32-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-trimethylsilylacetylenylcyclopent-1-enyl)-3-trimethylsilylpropyn-1-one
• 英文别名: 3-Trimethylsilyl-1-[2-(2-trimethylsilylethynyl)cyclopenten-1-yl]prop-2-yn-1-one
• CAS: 915378-32-4
• 化学式: C₁₆H₂₄OSi₂
• 分子量: 288.537
• InChiKey: NXSWXVRHSHCNGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(2-trimethylsilylacetylenylcyclopent-1-enyl)-3-trimethylsilylpropyn-1-one 在 copper(l) iodide 、 1,4-环己二烯 、 甲基锂 作用下， 以 乙醚 、 苯 为溶剂， 反应 5.08h， 生成 1-(2-ethynylcyclopent-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：

  三甲基乙炔基硅 、 2-trimethylsilylacetylenylcyclopent-1-ene-N-methoxy-N-methylcarboxamide 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.83h， 以80%的产率得到1-(2-trimethylsilylacetylenylcyclopent-1-enyl)-3-trimethylsilylpropyn-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