(E)-β-(2-pyridyldimethylsilyl)-4-methoxystyrene | 795311-52-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-β-(2-pyridyldimethylsilyl)-4-methoxystyrene
• 英文别名: [(E)-2-(4-methoxyphenyl)ethenyl]-dimethyl-pyridin-2-ylsilane
• CAS: 795311-52-3
• 化学式: C₁₆H₁₉NOSi
• 分子量: 269.418
• InChiKey: BSCWHCJMMFPXAN-ACCUITESSA-N

物化性质

• 沸点：
  387.7±27.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.26
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-β-(2-pyridyldimethylsilyl)-4-methoxystyrene 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex copper(l) iodide 、 三叔丁基膦 、 三乙胺 、 cesium fluoride 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 3.0h， 生成 4-[(1Z,3Z)-4-(4-cyanophenyl)-1,4-bis(4-methoxyphenyl)buta-1,3-dienyl]benzonitrile
  参考文献：
  名称：

  Stereoselective Synthesis of Multisubstituted Butadienes through Directed Mizoroki−Heck Reaction and Homocoupling Reaction of Vinyl(2-pyridyl)silane

  摘要：

  We have developed the homocoupling reaction of alkenyl(2-pyridyl)silanes mediated by Cul and CsF, in which the strong directing effect of the 2-pyridyl group was observed. The homocoupling reaction was successfully integrated with the Mizoroki-Heck reaction of vinyl(2-pyridyl)silane with aryl halides, enabling a rapid and stereoselective synthesis of multisubstituted butadienes. From a relatively small compound library, it was possible to detect a number of fluorescent butadienes with a wide range of fluorescence color variations (blue to reddish-orange).

  DOI：

  10.1021/ol048620i
• 作为产物：
  描述：

  4-碘苯甲醚 、 2-(二甲基乙烯基硅)吡啶 在 tris(dibenzylideneacetone)dipalladium (0) 三(2-呋喃基)膦 、 三乙胺 作用下， 以97%的产率得到(E)-β-(2-pyridyldimethylsilyl)-4-methoxystyrene
  参考文献：
  名称：

  基于三芳基乙烯的扩展π系统：可编程合成和光物理性质

  摘要：

  在有效的Pd催化的乙烯基硅烷三芳基化反应的基础上，已经非常快速地制备了四种类型的结构明确的基于三芳基乙烯的扩展π系统。从通过本方法构建的化合物库中，可以找到许多有趣的荧光材料，以及有趣的荧光特性，例如聚集诱导的增强发射。还开发了一种用于快速合成和性质评估的有用方法。

  DOI：

  10.1021/jo0477401

文献信息

• Iron-Catalyzed, Directed Oxidative Arylation of Olefins with Organozinc and Grignard Reagents
  作者：Laurean Ilies、Jun Okabe、Naohiko Yoshikai、Eiichi Nakamura

  DOI：10.1021/ol1009448

  日期：2010.6.18

  Chelation-controlled arylation of olefins with organozinc or Grignard reagents proceeds in the presence of an iron catalyst, under mild conditions and typically without the need of external ligands, to afford substituted olefins in high yield and with complete regio- and stereocontrol.

  烯烃与有机锌或格氏试剂的螯合控制的芳基化反应在铁催化剂的存在下，在温和的条件下且通常不需要外部配体的情况下进行，从而以高收率和完全的区域和立体控制提供了取代的烯烃。
• Stereoselective Synthesis of Multisubstituted Butadienes through Directed Mizoroki−Heck Reaction and Homocoupling Reaction of Vinyl(2-pyridyl)silane
  作者：Kenichiro Itami、Yousuke Ushiogi、Toshiki Nokami、Youichi Ohashi、Jun-ichi Yoshida

  DOI：10.1021/ol048620i

  日期：2004.10.1

  We have developed the homocoupling reaction of alkenyl(2-pyridyl)silanes mediated by Cul and CsF, in which the strong directing effect of the 2-pyridyl group was observed. The homocoupling reaction was successfully integrated with the Mizoroki-Heck reaction of vinyl(2-pyridyl)silane with aryl halides, enabling a rapid and stereoselective synthesis of multisubstituted butadienes. From a relatively small compound library, it was possible to detect a number of fluorescent butadienes with a wide range of fluorescence color variations (blue to reddish-orange).
• Triarylethene-Based Extended π-Systems:  Programmable Synthesis and Photophysical Properties
  作者：Kenichiro Itami、Youichi Ohashi、Jun-ichi Yoshida

  DOI：10.1021/jo0477401

  日期：2005.4.1

  structurally well-defined triarylethene-based extended π-systems have been prepared very rapidly. From a compound library constructed by the present method, it was possible to find a number of interesting fluorescent materials, as well as interesting fluorescent properties such as aggregation-induced enhanced emission. A useful method for the rapid synthesis and property evaluation has also been developed

  在有效的Pd催化的乙烯基硅烷三芳基化反应的基础上，已经非常快速地制备了四种类型的结构明确的基于三芳基乙烯的扩展π系统。从通过本方法构建的化合物库中，可以找到许多有趣的荧光材料，以及有趣的荧光特性，例如聚集诱导的增强发射。还开发了一种用于快速合成和性质评估的有用方法。