(E)-4-(2-trimethylsilanylvinyl)benzoic acid ethyl ester | 107099-30-9

• 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)-4-(2-trimethylsilanylvinyl)benzoic acid ethyl ester
• 英文别名: (E)-ethyl 4-(2-(trimethylsilyl)vinyl)benzoate；ethyl 4-[(E)-2-trimethylsilylethenyl]benzoate
• CAS: 107099-30-9
• 化学式: C₁₄H₂₀O₂Si
• 分子量: 248.397
• InChiKey: LKKAUFOCCPEBDU-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  ethyl 4-(trimethylsilylethynyl)benzoate 在 四(三苯基膦)钯 、 乙醇 、 potassium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.58h， 生成 (E)-4-(2-trimethylsilanylvinyl)benzoic acid ethyl ester
  参考文献：
  名称：

  Synthesis of 1,1-diarylethylenes from an α-stannyl β-silylstyrene

  摘要：

  The synthesis of a family of 1,1-diaryiethylenes from an alpha-stannyl beta-silylstyrene through a combination of a Stille coupling and a protodesilylation reaction is described. This approach avoids the problematic cine-substitution, which is a well documented side reaction during the palladium-assisted elaboration of a-substituted vinylstannanes to 1,1-disubstituted ethylenes. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.12.106

文献信息

• Preparation of Allyl and Vinyl Silanes by the Palladium-Catalyzed Silylation of Terminal Olefins: A Silyl-Heck Reaction
  作者：Jesse R. McAtee、Sara E. S. Martin、Derek T. Ahneman、Keywan A. Johnson、Donald A. Watson

  DOI：10.1002/anie.201200060

  日期：2012.4.10

  high‐yielding protocol for the palladium‐catalyzed silylation of terminal alkenes is reported. This method allows facile conversion of styrenes to E‐β‐silyl styrenes by using iodotrimethylsilane (TMSI) or chlorotrimethylsilane/lithium iodide (see scheme). Terminal allyl silanes with good E/Z ratios are also readily accessed from α‐olefins.

  安装硅很容易！报道了钯催化的末端烯烃硅烷化的高产率方案。该方法可以通过使用碘三甲基硅烷 (TMSI) 或氯三甲基硅烷/碘化锂轻松将苯乙烯转化为E -β-甲硅烷基苯乙烯（参见方案）。具有良好E / Z比的末端烯丙基硅烷也很容易从 α-烯烃中获得。
• Simplified Preparation of Trialkylvinylsilanes<i>via</i>the Silyl-Heck Reaction Utilizing a Second Generation Catalyst
  作者：Jesse R. McAtee、Sarah B. Krause、Donald A. Watson

  DOI：10.1002/adsc.201500436

  日期：2015.7.6

  bis(3,5‐di‐tert‐butylphenyl)(tert‐butyl)phosphine, for the preparation of allylsilanes using the silyl‐Heck reaction. We now show that this new ligand also provides superior reactivity in the preparation of vinylsilanes from styrene derivatives. For the first time, this new ligand provides exceptionally high yields of trialkylvinylsilanes using the widely available palladium pre‐catalyst, tris(dibenzy

  最近，我们报道了第二代配体，双（3,5-二叔丁基苯基）（叔丁基）膦，用于使用甲硅烷基-Heck反应制备烯丙基硅烷。现在我们表明，这种新的配体在由苯乙烯衍生物制备乙烯基硅烷中也提供了优异的反应性。该新型配体首次使用广泛可用的钯预催化剂三（二亚苄基丙酮）二钯（0）[Pd 2（dba）3 ]提供了极高的三烷基乙烯基硅烷收率。最后，我们证明了这种新的催化剂体系能够形成装饰更高级的全碳取代乙烯基硅烷，这些硅烷已显示出在氧化和交叉偶联反应中具有优异的反应活性。
• Stereospecific arylation of alkenylsilanes with arylpalladium acetates
  作者：Kazutoshi Ikenaga、Kiyoshi Kikukawa、Tsutomu Matsuda

  DOI：10.1021/jo00383a019

  日期：1987.4
• IKENAGA KAZUTOSHI; KIKUKAWA KIYOSHI; MATSUDA TSUTOMU, J. ORG. CHEM., 52,(1987) N 7, 1276-1280
  作者：IKENAGA KAZUTOSHI、 KIKUKAWA KIYOSHI、 MATSUDA TSUTOMU

  DOI：——

  日期：——
• Synthesis of 1,1-diarylethylenes from an α-stannyl β-silylstyrene
  作者：Makonen Belema、Van N. Nguyen、F. Christopher Zusi

  DOI：10.1016/j.tetlet.2003.12.106

  日期：2004.2

  The synthesis of a family of 1,1-diaryiethylenes from an alpha-stannyl beta-silylstyrene through a combination of a Stille coupling and a protodesilylation reaction is described. This approach avoids the problematic cine-substitution, which is a well documented side reaction during the palladium-assisted elaboration of a-substituted vinylstannanes to 1,1-disubstituted ethylenes. (C) 2004 Elsevier Ltd. All rights reserved.