4-methoxystyryltrimethylsilane

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-methoxystyryltrimethylsilane
• 英文别名: 2-(4-Methoxyphenyl)ethenyl-trimethylsilane
• 化学式: C₁₂H₁₈OSi
• 分子量: 206.36
• InChiKey: XBCCXDQOKCBZPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  4-methoxystyryltrimethylsilane 在 bis(dibenzylideneacetone)-palladium⁽⁰⁾ potassium fluoride 、 四丁基氯化铵 、 三氯化硼 、 四丁基碘化铵 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 6.0h， 生成 白藜芦醇
  参考文献：
  名称：

  One-pot palladium-catalyzed highly chemo-, regio-, and stereoselective synthesis of trans-stilbene derivatives. A concise and convenient synthesis of resveratrol

  摘要：

  A convenient, efficient and highly chemo-, regio-, and stereoselective one-flask synthetic method is reported for the construction of unsymmetrical (or symmetrical) trans-stilbene derivatives based on two sequential Heck-type reactions using tetraalkylammonium salt-based catalyst systems and vinyltrimethylsilane as double bond equivalent. Resveratrol has thus been concisely synthesized. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02317-1
• 作为产物：
  描述：

  4-碘苯甲醚 、 乙烯基三甲基硅烷 在 bis(dibenzylideneacetone)-palladium⁽⁰⁾ potassium fluoride 、 四丁基氯化铵 作用下， 以 甲苯 为溶剂， 生成 4-methoxystyryltrimethylsilane
  参考文献：
  名称：

  One-pot palladium-catalyzed highly chemo-, regio-, and stereoselective synthesis of trans-stilbene derivatives. A concise and convenient synthesis of resveratrol

  摘要：

  A convenient, efficient and highly chemo-, regio-, and stereoselective one-flask synthetic method is reported for the construction of unsymmetrical (or symmetrical) trans-stilbene derivatives based on two sequential Heck-type reactions using tetraalkylammonium salt-based catalyst systems and vinyltrimethylsilane as double bond equivalent. Resveratrol has thus been concisely synthesized. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02317-1

文献信息

• Rapid and efficient entry to vinyl silanes from aldehydes employing a novel metalation–Peterson sequence
  作者：James McNulty、Priyabrata Das

  DOI：10.1039/b716897g

  日期：——

  Bis(trimethylsilyl)chloromethane undergoes a rapid and selective metalation with s-BuLi, yielding the nucleophilic bis(trimethylsilyl)methyl anion and providing a straightforward general entry to vinyl silanes from aromatic, aliphatic and vinyl aldehydes.

  双（三甲基甲硅烷基）氯甲烷与s-BuLi进行快速选择性的金属化反应，生成亲核性双（三甲基甲硅烷基）甲基阴离子，并提供了从芳族，脂肪族和乙烯基醛类直接进入乙烯基硅烷的一般方法。
• Highly Enantioselective Alkenylation of Glyoxylate with Vinylsilane Catalyzed by Chiral Dicationic Palladium(II) Complexes
  作者：Kohsuke Aikawa、Yu̅ta Hioki、Koichi Mikami

  DOI：10.1021/ja906164p

  日期：2009.10.7

  Chiral dicationic palladium complex-catalyzed vinylation and dienylation of glyoxylate with vinylsilanes and dienylsilanes to produce highly optical active allylic alcohols has been achieved. The advantages of this reaction are that the chiral palladium catalyst is readily employed and that vinylsilanes as nucleophiles are easily synthesized, storable, and air- and moisture-stable.

  已经实现了手性双阳离子钯配合物催化乙醛酸与乙烯基硅烷和二烯基硅烷的乙烯基化和二烯化，以生产高光学活性的烯丙醇。该反应的优点是手性钯催化剂易于使用，并且乙烯基硅烷作为亲核试剂易于合成、储存、空气和湿气稳定。
• Light-driven radical-polar crossover catalysis for cross-coupling with organosilanes
  作者：Tomotoki Matsuo、Kazunori Nagao、Hirohisa Ohmiya

  DOI：10.1016/j.tetlet.2022.154231

  日期：2022.12

  enabling the cross-coupling between aliphatic carboxylic acid-derived redox active esters and organosilanes. In this protocol, a carbocation equivalent generated from the redox active ester by radical-polar crossover process could react with an organosilane reagent. This protocol allows to forge C(sp3)–C(sp3), C(sp3)–C(sp2) and C(sp3)–C(sp) bonds under transition-metal free and mild reaction conditions

  在本次交流中，我们报告了一种可见光介导的有机光氧化还原催化，可实现脂肪族羧酸衍生的氧化还原活性酯和有机硅烷之间的交叉偶联。在该协议中，通过自由基-极性交叉过程从氧化还原活性酯产生的碳阳离子当量可以与有机硅烷试剂反应。该协议允许在无过渡金属和温和的反应条件下形成 C(sp 3 )–C(sp 3 )、C(sp 3 )–C(sp 2 ) 和 C(sp 3 )–C(sp) 键。自由基介导过程的特权特征被证明是使用有机硅烷和脂肪族氧化还原活性酯对苯乙烯衍生物进行自由基中继型双碳官能化。
• Supported palladium nanoparticles as heterogeneous ligand-free catalysts for the Hiyama C–C coupling of vinylsilanes and halobenzenes leading to styrenes
  作者：Abdessamad Grirrane、Hermenegildo Garcia、Avelino Corma

  DOI：10.1016/j.jcat.2013.02.019

  日期：2013.6

  The Hiyama C-C coupling reaction of a wide range of aryl iodides and vinylsilanes has been performed using ligand-free solid catalysts based on supported palladium nanoparticles. Among the supports tested (Mg, TiO2, CeO2 and active carbon), the most active catalysts were those in which palladium is supported on MgO and TiO2. Analogous Pt and Au materials were inefficient to promote this reaction. Leaching tests suggest that there is some contribution of dissolved Pd since Pd in solution has been detected and the scavenging test decreases the initial reaction rate. Although the solid Pd catalysts can be reused, it was, however, observed that they undergo a certain deactivation upon use that can be attributed to several factors including the presence of inorganic compounds on the catalyst, Pd leaching or agglomeration of Pd NPs. (c) 2013 Elsevier Inc. All rights reserved.
• Copper-Mediated Cross-Coupling of <i>H</i>-Phosphonates with Vinyliodonium Salts: A Novel Very Mild Synthesis of 2-Arylvinylphosphonates
  作者：Sabine Thielges、Philippe Bisseret、Jacques Eustache

  DOI：10.1021/ol047516y

  日期：2005.2.1

  We report a novel, very mild, highly stereoselective preparation of 2-arylvinylphosphonates at room temperature that involves the copper iodide-mediated cross-coupling of H-phosphonates with vinyliodonium tetrafluoroborates.