(E,E)-1-(4-acetylphenyl)-4-(4-methylphenyl)buta-1,3-diene

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E,E)-1-(4-acetylphenyl)-4-(4-methylphenyl)buta-1,3-diene
• 英文别名: 1-[4-[(1E,3E)-4-(4-methylphenyl)buta-1,3-dienyl]phenyl]ethanone
• 化学式: C₁₉H₁₈O
• 分子量: 262.351
• InChiKey: LQZCLWBIEZPUEZ-GGWOSOGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (E,E)-[4-(4-methylphenyl)-1,3-butadienyl]dimethylbenzylsilane 、 4-碘代苯乙酮 在 四丁基氟化铵 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以90%的产率得到(E,E)-1-(4-acetylphenyl)-4-(4-methylphenyl)buta-1,3-diene
  参考文献：
  名称：

  Sequential Cross-Coupling of 1,4-Bissilylbutadienes:  Synthesis of Unsymmetrical 1,4-Disubstituted 1,3-Butadienes

  摘要：

  A mild and general and stereospecific cross-coupling reaction of unsymmetrical 1,4-bissilyl-1,3-butadienes has been accomplished. By the use of either a benzyldimethylsilyl or 2-thienyldimethylsilyl unit at one end of the dienylsilanol, a selective cross-coupling could be effected under mildly basic conditions (KOTMS) to afford 4-aryl-1,3-dienylsilanes in excellent yield for a wide range of aryl and alkenyl coupling partners. The second cross-coupling could be effected cleanly by the action of TBAF with electron-rich or electron-poor halides. The sequential process could be telescoped into a "one pot" procedure with overall excellent yields of the unsymmetrical 1,4-diaryl-1,3-butadienes.

  DOI：

  10.1021/ja0518373

文献信息

• Cyclic 1,1-bis(silyl)alkenes—new building blocks for the stereoselective synthesis of unsymmetrical (E)-stilbenes and (E,E)-1,4-diarylbuta-1,3-dienes
  作者：Piotr Pawluć、Grzegorz Hreczycho、Andrzej Suchecki、Maciej Kubicki、Bogdan Marciniec

  DOI：10.1016/j.tet.2009.01.113

  日期：2009.7

  A new efficient synthetic protocol for the highly stereoselective synthesis Of Unsymmetrical (or symmetrical) (E)-stilbenes and (E,E)-1,4-diarylbuta-1,3-dienes based on sequential palladium-catalyzed Heck arylation-Hiyama cross-coupling reactions using cyclic gem-bis(silyl)ethene as alkenyl building block is reported. (C) 2009 Elsevier Ltd. All rights reserved.
• Sequential Cross-Coupling of 1,4-Bissilylbutadienes:  Synthesis of Unsymmetrical 1,4-Disubstituted 1,3-Butadienes
  作者：Scott E. Denmark、Steven A. Tymonko

  DOI：10.1021/ja0518373

  日期：2005.6.1

  A mild and general and stereospecific cross-coupling reaction of unsymmetrical 1,4-bissilyl-1,3-butadienes has been accomplished. By the use of either a benzyldimethylsilyl or 2-thienyldimethylsilyl unit at one end of the dienylsilanol, a selective cross-coupling could be effected under mildly basic conditions (KOTMS) to afford 4-aryl-1,3-dienylsilanes in excellent yield for a wide range of aryl and alkenyl coupling partners. The second cross-coupling could be effected cleanly by the action of TBAF with electron-rich or electron-poor halides. The sequential process could be telescoped into a "one pot" procedure with overall excellent yields of the unsymmetrical 1,4-diaryl-1,3-butadienes.