(E)-[1-(4-methylphenyl)-2-(1,1,3,3,3-pentamethyldisiloxy)]ethene

• 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: (E)-[1-(4-methylphenyl)-2-(1,1,3,3,3-pentamethyldisiloxy)]ethene
• 英文别名: dimethyl-[(E)-2-(4-methylphenyl)ethenyl]-trimethylsilyloxysilane
• 化学式: C₁₄H₂₄OSi₂
• 分子量: 264.515
• InChiKey: DYFMIFSWYLCMGU-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  溴苯 、 (E)-[1-(4-methylphenyl)-2-(1,1,3,3,3-pentamethyldisiloxy)]ethene 在 [PdCl₂P(OCH₂CMe₂NH)OCH₂CMe₂NH₂] 、 四丁基氟化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以92%的产率得到1-甲基-4-((e)-苯乙烯)-苯
  参考文献：
  名称：

  An efficient synthesis of functional stilbenes in Hiyama coupling reaction catalysed by H-spirophosphorane palladium complex

  摘要：

  An efficient Hiyama cross-coupling reaction of functionalised styrylsilanes with iodo- and bromobenzene has been performed using complex [PdCl2P(OCH2CMe2NH) OCH2CMe2NH2] as precatalyst. The styrylsilanes underwent cross-coupling reactions with excellent selectivity and yield, up to 99%, of the corresponding E-stilbenes. When (E)-[1-(4-bromophenyl)-2-(1,1,3,3,3-pentamethyldisiloxy)]ethene was used as a source of the silane, a homocoupling reaction took place and polymeric compound containing 0.77% of palladium in the form of Pd(0) nanoparticles was obtained. This material used as a catalyst made it possible to obtain 40% and 38% of the Hiyama cross-coupling product in two subsequent runs. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2011.09.025
• 作为产物：
  描述：

  4-MeC6H4CH=CHSiMe2OSiMe3 在 五甲基二硅氧烷 、 RhI(PPh₃)3 作用下， 反应 1.0h， 生成 (E)-[1-(4-methylphenyl)-2-(1,1,3,3,3-pentamethyldisiloxy)]ethene
  参考文献：
  名称：

  Isomerization of (Z)-alkenylsilanes to (E)-isomers with hydrosilane and RhI(PPh₃)₃

  摘要：

  (E)-2-苯乙烯基硅烷的异构化反应在60°C下，使用20-100 mol％的硅氢化合物和0.1 mol％的RhI（PPh3）3催化剂，1小时内易于发生转化为（Z）异构体，其机理是通过烯基硅烷插入到氢化铑中，然后进行β-氢化物消除。关键词：硅氢化，异构化，RhI（PPh3）3，烯基硅烷，硅氢化合物。

  DOI：

  10.1139/v01-129

文献信息

• An efficient synthesis of functional stilbenes in Hiyama coupling reaction catalysed by H-spirophosphorane palladium complex
  作者：Anna Skarżyńska、Mariusz Majchrzak、Anna M. Trzeciak、Bogdan Marciniec

  DOI：10.1016/j.molcata.2011.09.025

  日期：2011.12

  An efficient Hiyama cross-coupling reaction of functionalised styrylsilanes with iodo- and bromobenzene has been performed using complex [PdCl2P(OCH2CMe2NH) OCH2CMe2NH2] as precatalyst. The styrylsilanes underwent cross-coupling reactions with excellent selectivity and yield, up to 99%, of the corresponding E-stilbenes. When (E)-[1-(4-bromophenyl)-2-(1,1,3,3,3-pentamethyldisiloxy)]ethene was used as a source of the silane, a homocoupling reaction took place and polymeric compound containing 0.77% of palladium in the form of Pd(0) nanoparticles was obtained. This material used as a catalyst made it possible to obtain 40% and 38% of the Hiyama cross-coupling product in two subsequent runs. (C) 2011 Elsevier B.V. All rights reserved.
• Isomerization of (<i>Z</i>)-alkenylsilanes to (<i>E</i>)-isomers with hydrosilane and RhI(PPh₃)₃
  作者：Atsunori Mori、Eisuke Takahisa、Yasushi Nishihara、Tamejiro Hiyama

  DOI：10.1139/v01-129

  日期：2001.11.1

  Isomerization of (E)-2-phenylethenylsilanes to the (Z)-isomers is found to easily take place at 60°C within 1 h using 20–100 mol% of a hydrosilane and 0.1 mol% of RhI(PPh₃)₃ and is understood in terms of insertion of alkenylsilanes to hydridorhodium followed by β-hydride elimination.Key words: hydrosilylation, isomerization, RhI(PPh₃)₃, alkenylsilane, hydrosilane.

  (E)-2-苯乙烯基硅烷的异构化反应在60°C下，使用20-100 mol％的硅氢化合物和0.1 mol％的RhI（PPh3）3催化剂，1小时内易于发生转化为（Z）异构体，其机理是通过烯基硅烷插入到氢化铑中，然后进行β-氢化物消除。关键词：硅氢化，异构化，RhI（PPh3）3，烯基硅烷，硅氢化合物。