3,3-Bis<(trimethylsilyl)ethynyl>-5-(trimethylsilyl)pent-4-ynal | 154317-67-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,3-Bis<(trimethylsilyl)ethynyl>-5-(trimethylsilyl)pent-4-ynal
• CAS: 154317-67-6
• 化学式: C₁₈H₃₀OSi₃
• 分子量: 346.692
• InChiKey: LAKJRTHJKGDOJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  3,3-Bis<(trimethylsilyl)ethynyl>-5-(trimethylsilyl)pent-4-ynal 在 正丁基锂 、 五氯化磷 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 0.53h， 生成 3-<(Trimethylsilyl)ethynyl>-5-(trimethylsilyl)penta-1,2-dien-4-yne
  参考文献：
  名称：

  Novel Products Derived from Unprecedented Transformations of 3,3,3-Trialkynylpropionaldehyde Derivatives

  摘要：

  DOI：

  10.1021/jo00084a049
• 作为产物：
  描述：

  2-bromo-5-(trimethylsilyl)-3-<(trimethylsilyl)ethynyl>pent-2-en-4-ynol 在 二异丁基氢化铝 、 丙酸 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 33.83h， 生成 3,3-Bis<(trimethylsilyl)ethynyl>-5-(trimethylsilyl)pent-4-ynal
  参考文献：
  名称：

  Preparation and Some Subsequent Transformations of Tetraethynylmethane

  摘要：

  Tetraethynylmethane (1) was synthesized in 10 steps and 33% overall yield from bis[(trimethysilyl)ethynyl] ketone. This route features (1) construction of the critical central quaternary center via the agency of a [3,3] sigmatropic shift and (2) installation of the fourth acetylene unit in a very sterically demanding environment. Alternative routes and model systems which were more informative than productive are also discussed. Finally, transition metal-mediated coupling of the rather unstable 1 (and derivatives) with unsaturated partners furnished a variety of relatively stable polylalkynylated species which could be manipulated without event.

  DOI：

  10.1021/ja00099a020

文献信息

• Preparation and Some Subsequent Transformations of Tetraethynylmethane
  作者：Ken S. Feldman、Carolyn K. Weinreb、Wiley J. Youngs、John D. Bradshaw

  DOI：10.1021/ja00099a020

  日期：1994.10

  Tetraethynylmethane (1) was synthesized in 10 steps and 33% overall yield from bis[(trimethysilyl)ethynyl] ketone. This route features (1) construction of the critical central quaternary center via the agency of a [3,3] sigmatropic shift and (2) installation of the fourth acetylene unit in a very sterically demanding environment. Alternative routes and model systems which were more informative than productive are also discussed. Finally, transition metal-mediated coupling of the rather unstable 1 (and derivatives) with unsaturated partners furnished a variety of relatively stable polylalkynylated species which could be manipulated without event.
• Novel Products Derived from Unprecedented Transformations of 3,3,3-Trialkynylpropionaldehyde Derivatives
  作者：Ken S. Feldman、Carolyn Kraebel Weinreb、Wiley J. Youngs、John D. Bradshaw

  DOI：10.1021/jo00084a049

  日期：1994.3