3,3-bis<(trimethylsilyl)ethynyl>-5-(trimethylsilyl)pent-1,4-diyne | 148549-34-2

• 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: 3,3-bis<(trimethylsilyl)ethynyl>-5-(trimethylsilyl)pent-1,4-diyne
• 英文别名: [3-Ethynyl-5-trimethylsilyl-3-(2-trimethylsilylethynyl)penta-1,4-diynyl]-trimethylsilane
• CAS: 148549-34-2
• 化学式: C₁₈H₂₈Si₃
• 分子量: 328.677
• InChiKey: TZIRDTXIXNLZDZ-UHFFFAOYSA-N

物化性质

• 沸点：
  294.5±35.0 °C(Predicted)
• 密度：
  0.896±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.25
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3,3-bis<(trimethylsilyl)ethynyl>-5-(trimethylsilyl)pent-1,4-diyne 在 四甲基乙二胺 、 copper(l) chloride 作用下， 以 丙酮 为溶剂， 反应 16.0h， 以78%的产率得到1,10-Bis-trimethylsilanyl-3,3,8,8-tetrakis-trimethylsilanylethynyl-deca-1,4,6,9-tetrayne
  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
• 作为产物：
  描述：

  2-(phenylsulfonyl)-3,3-bis<(trimethylsilyl)ethynyl>-5-(trimethylsilyl)pent-4-ynal <(2,4,6-triisopropylphenyl)sulfonyl>hydrazone 在 lithium hydroxide 作用下， 以 乙醚 为溶剂， 反应 24.0h， 以74%的产率得到3,3-bis<(trimethylsilyl)ethynyl>-5-(trimethylsilyl)pent-1,4-diyne
  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

• Tetraethynylmethane
  作者：Ken S. Feldman、Carolyn M. Kraebel、Masood Parvez

  DOI：10.1021/ja00062a089

  日期：1993.5
• Feldman Ken S., Weinreb Carolyn K., Youngs Wiley J., Bradshaw John D., J. Amer. Chem. Soc, 116 (1994) N 20, S 9019-9026
  作者：Feldman Ken S., Weinreb Carolyn K., Youngs Wiley J., Bradshaw John D.

  DOI：——

  日期：——
• 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.