ethyl 2-(phenylthio)-3,3-bis<(trimethylsilyl)ethynyl>-5-(trimethylsilyl)pent-4-ynoate | 148549-35-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: ethyl 2-(phenylthio)-3,3-bis<(trimethylsilyl)ethynyl>-5-(trimethylsilyl)pent-4-ynoate
• CAS: 148549-35-3
• 化学式: C₂₆H₃₈O₂SSi₃
• 分子量: 498.909
• InChiKey: OIZNIABNXIXQHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.34
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-(phenylthio)-3,3-bis<(trimethylsilyl)ethynyl>-5-(trimethylsilyl)pent-4-ynoate 在 二异丁基氢化铝 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 1.5h， 生成 2-(phenylsulfonyl)-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
• 作为产物：
  描述：

  2-bromo-5-(trimethylsilyl)-3-<(trimethylsilyl)ethynyl>pent-2-en-4-ynol 在 丙酸 、 lithium diisopropyl amide 作用下， 反应 50.5h， 生成 ethyl 2-(phenylthio)-3,3-bis<(trimethylsilyl)ethynyl>-5-(trimethylsilyl)pent-4-ynoate
  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
• 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.