1-{4-[(E)-2-(Dimethyl-pyridin-2-yl-silanyl)-vinyl]-phenyl}-ethanone | 795311-24-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-{4-[(E)-2-(Dimethyl-pyridin-2-yl-silanyl)-vinyl]-phenyl}-ethanone
• CAS: 795311-24-9
• 化学式: C₁₇H₁₉NOSi
• 分子量: 281.429
• InChiKey: HVEGWLBIKNLZQC-ACCUITESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  29.96
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-{4-[(E)-2-(Dimethyl-pyridin-2-yl-silanyl)-vinyl]-phenyl}-ethanone 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 5.0h， 生成 1-{4-[(1E,3E)-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：

  4-碘代苯乙酮 、 2-(二甲基乙烯基硅)吡啶 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 三(2-呋喃基)膦 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以71%的产率得到1-{4-[(E)-2-(Dimethyl-pyridin-2-yl-silanyl)-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