(E)-4-(2-triethylsilanylvinyl)acetophenone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-4-(2-triethylsilanylvinyl)acetophenone
• 英文别名: (E)-1-(4-(2-(triethylsilyl)vinyl)phenyl)ethanone；1-[4-[(E)-2-triethylsilylethenyl]phenyl]ethanone
• 化学式: C₁₆H₂₄OSi
• 分子量: 260.451
• InChiKey: BHEQSGOAGCNSDG-OUKQBFOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.95
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  三乙基硅烷 、 1-(4-乙烯基-苯基)-乙酮 在 降冰片烯 、 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以52%的产率得到(E)-4-(2-triethylsilanylvinyl)acetophenone
  参考文献：
  名称：

  以NBE为氢受体的[Rh（COD）Cl] 2 / PPh 3-催化苯乙烯衍生物的脱氢硅烷化

  摘要：

  通过[Rh（COD）Cl] 2 / PPh 3催化苯乙烯衍生物与R 3 SiH（R =烷基，烷氧基，芳基）的直接合成芳基烯基硅烷，其中降冰片烯（NBE）和PPh 3起着在脱氢甲硅烷基化产物的形成中达到极好的选择性的关键作用。而且，这种高产率的转化表现出广泛的底物范围和良好的官能团耐受性。

  DOI：

  10.1021/acs.organomet.0c00242

文献信息

• Selective synthesis of (E)-triethyl(2-arylethenyl)silane derivatives by reaction of aryl bromides with triethyl vinylsilane catalysed by a palladium–tetraphosphine complex
  作者：Ahmed Battace、Touriya Zair、Henri Doucet、Maurice Santelli

  DOI：10.1016/j.jorganchem.2005.05.014

  日期：2005.8

  Cis, cis, cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane/0.5[PdCI(C3H5)](2) system catalyses the Heck reaction of vinylsilane derivatives with a range of aryl bromides with high ratio substrate/catalyst in good yields. The formation of mixtures of styrene, (E)-triethyl(2-arylethenyl)sitane and triethyl(1-arylethenyl)silane derivatives was observed in some cases. Very high selectivities (up to 100%) in favour of the formation of (E)-triethyl(2-arylethenyl)silane derivatives were obtained in the presence of sodium acetate as base. With other bases such as potassium carbonate, the formation of large amounts of styrene derivatives was observed. The reaction tolerates several functions such as fluoro, trifluoromethyl, methoxy, dimethylamino, acetyl, formyl, benzoyl, carboxylate, nitro or nitrile. Moreover, turnover numbers up to 10,000 can be obtained for this reaction. (c) 2005 Elsevier B.V. All rights reserved.
• [Rh(COD)Cl]₂/PPh₃-Catalyzed Dehydrogenative Silylation of Styrene Derivatives with NBE as a Hydrogen Acceptor
  作者：Wenkui Lu、Chengyang Li、Xiaoyu Wu、Xiaomin Xie、Zhaoguo Zhang

  DOI：10.1021/acs.organomet.0c00242

  日期：2020.11.9

  Direct synthesis of arylalkenylsilanes by [Rh(COD)Cl]2/PPh3-catalyzed dehydrogenative silylation of styrene derivatives with R3SiH (R = alkyl, alkoxy, aryl) was realized, in which norbornene (NBE) and PPh3 play a key role in achieving excellent selectivity in the formation of dehydrogenative silylation products. Moreover, this high-yielding transformation exhibits a broad substrate scope and good functional

  通过[Rh（COD）Cl] 2 / PPh 3催化苯乙烯衍生物与R 3 SiH（R =烷基，烷氧基，芳基）的直接合成芳基烯基硅烷，其中降冰片烯（NBE）和PPh 3起着在脱氢甲硅烷基化产物的形成中达到极好的选择性的关键作用。而且，这种高产率的转化表现出广泛的底物范围和良好的官能团耐受性。