5-(trimethylsilyl)-3-<(trimethylsilyl)ethynyl>pent-2-en-4-ynyl acetate

• 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: 5-(trimethylsilyl)-3-<(trimethylsilyl)ethynyl>pent-2-en-4-ynyl acetate
• 英文别名: [5-trimethylsilyl-3-(2-trimethylsilylethynyl)pent-2-en-4-ynyl] acetate
• 化学式: C₁₅H₂₄O₂Si₂
• 分子量: 292.525
• InChiKey: ACJLGEBQSOOQQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.24
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  1,5-双(三甲硅烷基)五-1,4-二炔-3-酮 在 吡啶 、 sodium hydride 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.75h， 生成 5-(trimethylsilyl)-3-<(trimethylsilyl)ethynyl>pent-2-en-4-ynyl acetate
  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

• 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.