(E)-1-ethoxydimethylsilyl-2-(4-methoxycarbonylphenyl)ethene | 1021190-28-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-1-ethoxydimethylsilyl-2-(4-methoxycarbonylphenyl)ethene
• 英文别名: methyl 4-[(E)-2-[ethoxy(dimethyl)silyl]ethenyl]benzoate
• CAS: 1021190-28-2
• 化学式: C₁₄H₂₀O₃Si
• 分子量: 264.397
• InChiKey: OSCDKMGGZLTVNF-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.27
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  二甲基乙氧基硅烷 、 4-乙炔基苯甲酸甲酯 在 platinum(II) chloride 2-dicyclohexyl-phosphino-2',4',6'-triisopropylbiphenyl 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (E)-1-ethoxydimethylsilyl-2-(4-methoxycarbonylphenyl)ethene 、 methyl 4-(1-(ethoxydimethylsilyl)vinyl)benzoate
  参考文献：
  名称：

  Xphos ligand and platinum catalysts: A versatile catalyst for the synthesis of functionalized β-(E)-vinylsilanes from terminal alkynes

  摘要：

  Hydrosilylation of functionalized terminal arylalkynes with a variety of silanes catalyzed by PtCl(2) or PtO(2) in the presence of the air-stable and bulky Xphos ligand was investigated. Regardless of the electronic nature ( electron withdrawing or donating group) and the position (o, m, p) of the substituents on the aromatic ring, a single beta-(E)-styrylsilanes was obtained in good to excellent yields. The regioselectivity of the H-Si bond addition was found to be governed by steric effects induced by the bulky Xphos ligand. A dramatic regioselectivity was also observed when functionalized terminal aliphatic alkynes were employed as a substrate and in these cases regioisomeric beta-(E)-vinylsilanes were generated with excellent selectivity. (c) 2008 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2008.05.028

文献信息

• Xphos ligand and platinum catalysts: A versatile catalyst for the synthesis of functionalized β-(E)-vinylsilanes from terminal alkynes
  作者：Abdallah Hamze、Olivier Provot、Jean-Daniel Brion、Mouâd Alami

  DOI：10.1016/j.jorganchem.2008.05.028

  日期：2008.8

  Hydrosilylation of functionalized terminal arylalkynes with a variety of silanes catalyzed by PtCl(2) or PtO(2) in the presence of the air-stable and bulky Xphos ligand was investigated. Regardless of the electronic nature ( electron withdrawing or donating group) and the position (o, m, p) of the substituents on the aromatic ring, a single beta-(E)-styrylsilanes was obtained in good to excellent yields. The regioselectivity of the H-Si bond addition was found to be governed by steric effects induced by the bulky Xphos ligand. A dramatic regioselectivity was also observed when functionalized terminal aliphatic alkynes were employed as a substrate and in these cases regioisomeric beta-(E)-vinylsilanes were generated with excellent selectivity. (c) 2008 Elsevier B. V. All rights reserved.
• Platinum chloride/Xphos-catalyzed regioselective hydrosilylation of functionalized terminal arylalkynes
  作者：Abdallah Hamze、Olivier Provot、Jean-Daniel Brion、Mouâd Alami

  DOI：10.1016/j.tetlet.2008.02.060

  日期：2008.4

  Totally regioselective hydrosilylation of functionalized terminal arylalkynes was achieved using PtCl(2) associated with the air-stable and bulky Xphos ligand with various silanes. Regardless of the electronic nature of the substituents on the aromatic ring, a single beta-(E)-vinylsilane was obtained in excellent yields. (C) 2008 Elsevier Ltd. All rights reserved.