1-{4-[(Z)-2-(Dimethyl-pyridin-2-yl-silanyl)-1-(4-methoxy-phenyl)-vinyl]-phenyl}-ethanone | 795311-31-8

• 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: 1-{4-[(Z)-2-(Dimethyl-pyridin-2-yl-silanyl)-1-(4-methoxy-phenyl)-vinyl]-phenyl}-ethanone
• 英文别名: 1-[4-[(Z)-2-[dimethyl(pyridin-2-yl)silyl]-1-(4-methoxyphenyl)ethenyl]phenyl]ethanone
• CAS: 795311-31-8
• 化学式: C₂₄H₂₅NO₂Si
• 分子量: 387.554
• InChiKey: QXUQXXMAVHSUCE-QJOMJCCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.88
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-{4-[(Z)-2-(Dimethyl-pyridin-2-yl-silanyl)-1-(4-methoxy-phenyl)-vinyl]-phenyl}-ethanone 在 copper(l) iodide 、 cesium fluoride 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以50%的产率得到1-{4-[(1Z,3Z)-4-(4-Acetyl-phenyl)-1,4-bis-(4-methoxy-phenyl)-buta-1,3-dienyl]-phenyl}-ethanone
  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：

  2-(二甲基乙烯基硅)吡啶 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 三(2-呋喃基)膦 、 三叔丁基膦 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 生成 1-{4-[(Z)-2-(Dimethyl-pyridin-2-yl-silanyl)-1-(4-methoxy-phenyl)-vinyl]-phenyl}-ethanone
  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

文献信息

• 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).