(E,E)-[4-(4-nitrophenyl)-1,3-butadienyl]dimethylbenzylsilane

• 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: (E,E)-[4-(4-nitrophenyl)-1,3-butadienyl]dimethylbenzylsilane
• 英文别名: benzyl-dimethyl-[(1E,3E)-4-(4-nitrophenyl)buta-1,3-dienyl]silane
• 化学式: C₁₉H₂₁NO₂Si
• 分子量: 323.467
• InChiKey: BTDDORZZNGFCGP-JKFVWBRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.19
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苄基二甲基氯硅烷 在 甲醇 、 Wilkinson's catalyst 、 t-Bu₃P*Pt(DVDS) 、 potassium trimethylsilonate 、 sodium methylate 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲苯 、 xylene 为溶剂， 反应 60.5h， 生成 (E,E)-[4-(4-nitrophenyl)-1,3-butadienyl]dimethylbenzylsilane
  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

• 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.