[(Z)-[2-(2-trimethylsilylethynyl)cyclohex-2-en-1-ylidene]methyl] trifluoromethanesulfonate | 156537-46-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: [(Z)-[2-(2-trimethylsilylethynyl)cyclohex-2-en-1-ylidene]methyl] trifluoromethanesulfonate
• CAS: 156537-46-1
• 化学式: C₁₃H₁₇F₃O₃SSi
• 分子量: 338.423
• InChiKey: MJDBKXOAUFVWMM-BENRWUELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.73
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(Z)-[2-(2-trimethylsilylethynyl)cyclohex-2-en-1-ylidene]methyl] trifluoromethanesulfonate 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide potassium fluoride 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 40.0h， 生成 2-[3-((E)-2-Ethynyl-2-cyclohexen-1-ylidene)-1-propynyl]benzaldehyde
  参考文献：
  名称：

  Eckhardt, Matthias; Brueckner, Reinhard, Liebigs Annalen, 1996, # 4, p. 473 - 488

  摘要：

  DOI：
• 作为产物：
  描述：

  (Z)-6-<(Trifluoromethylsulfonyloxy)methylene>-1-cyclohexen-1-yl trifluoromethanesulfonate 、 三甲基乙炔基硅 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 正丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 22.5h， 生成 [(Z)-[2-(2-trimethylsilylethynyl)cyclohex-2-en-1-ylidene]methyl] trifluoromethanesulfonate
  参考文献：
  名称：

  Study of the regioselectivity of palladium-catalyzed monocouplings between conjugated bis(enoltriflates) and trimethylsilylacetylene

  摘要：

  The Z-configurated bis(enoltriflates) 2 and 7 were treated at room temperature with TMS acetylene (1.25 equiv.) in the presence of CuI (0. 17 equiv.) and various palladium catalysts (0.07 equiv.), solvents, and amines to afford monocoupling products. Surprisingly, opposite regioselectivities were observed starting from the five-membered (-->8, n = 0) vs. the six-membered bis(enoltriflates) (-->9, n = 1).

  DOI：

  10.1016/s0040-4039(00)73023-1

文献信息

• The First 6-Membered/10-Membered Ring Analogues of the Dienediyne Core of Neocarzinostatin Chromophore
  作者：M Eckhardt

  DOI：10.1016/00404-0399(50)1025d-

  日期：1995.7.17
• Eckhardt, Matthias; Brueckner, Reinhard, Liebigs Annalen, 1996, # 4, p. 473 - 488
  作者：Eckhardt, Matthias、Brueckner, Reinhard

  DOI：——

  日期：——
• Study of the regioselectivity of palladium-catalyzed monocouplings between conjugated bis(enoltriflates) and trimethylsilylacetylene
  作者：Marc Moniatte、Matthias Eckhardt、Kay Brickmann、Reinhard Brückner、Jean Suffert

  DOI：10.1016/s0040-4039(00)73023-1

  日期：1994.3

  The Z-configurated bis(enoltriflates) 2 and 7 were treated at room temperature with TMS acetylene (1.25 equiv.) in the presence of CuI (0. 17 equiv.) and various palladium catalysts (0.07 equiv.), solvents, and amines to afford monocoupling products. Surprisingly, opposite regioselectivities were observed starting from the five-membered (-->8, n = 0) vs. the six-membered bis(enoltriflates) (-->9, n = 1).