(E)-1-dimethylethoxysilyl-2-(4-methoxyphenyl)ethene | 1054612-39-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-1-dimethylethoxysilyl-2-(4-methoxyphenyl)ethene
• 英文别名: ethoxy-[(E)-2-(4-methoxyphenyl)ethenyl]-dimethylsilane
• CAS: 1054612-39-3
• 化学式: C₁₃H₂₀O₂Si
• 分子量: 236.386
• InChiKey: SPXBLHITEMXGRP-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.49
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1-dimethylethoxysilyl-2-(4-methoxyphenyl)ethene 、 苯基三氟甲烷磺酸酯 在 tris-(dibenzylideneacetone)dipalladium(0) 、 四丁基氟化铵 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以95%的产率得到1-甲氧基-4-((E)-苯乙烯基)-苯
  参考文献：
  名称：

  通过甲硅烷基二氟甲磺酸酯的甲硅烷基-赫克反应制备乙烯基甲硅烷基醚和二硅氧烷

  摘要：

  现在可以使用甲硅烷基-Heck 反应从芳基取代的烯烃和相关底物制备乙烯基甲硅烷基醚和二硅氧烷。该反应采用市售的催化剂体系和温和的条件。这项工作代表了一种非常实用的方法，可以以有效和直接的方式获得不同类别的乙烯基甲硅烷基醚底物，并具有完全的区域异构和几何选择性。

  DOI：

  10.1021/ja407748z
• 作为产物：
  描述：

  二甲基乙氧基硅烷 、 4-乙炔基苯甲醚 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， 以83%的产率得到(E)-1-dimethylethoxysilyl-2-(4-methoxyphenyl)ethene
  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

• Preparation of Vinyl Silyl Ethers and Disiloxanes via the Silyl-Heck Reaction of Silyl Ditriflates
  作者：Sara E. S. Martin、Donald A. Watson

  DOI：10.1021/ja407748z

  日期：2013.9.11

  Vinyl silyl ethers and disiloxanes can now be prepared from aryl-substituted alkenes and related substrates using a silyl-Heck reaction. The reaction employs a commercially available catalyst system and mild conditions. This work represents a highly practical means of accessing diverse classes of vinyl silyl ether substrates in an efficient and direct manner with complete regiomeric and geometric selectivity

  现在可以使用甲硅烷基-Heck 反应从芳基取代的烯烃和相关底物制备乙烯基甲硅烷基醚和二硅氧烷。该反应采用市售的催化剂体系和温和的条件。这项工作代表了一种非常实用的方法，可以以有效和直接的方式获得不同类别的乙烯基甲硅烷基醚底物，并具有完全的区域异构和几何选择性。
• 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.