(E,E)-[4-(4-methoxyphenyl)-1,3-butadienyl]dimethylbenzylsilane | 857350-07-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E,E)-[4-(4-methoxyphenyl)-1,3-butadienyl]dimethylbenzylsilane
• 英文别名: benzyl-[(1E,3E)-4-(4-methoxyphenyl)buta-1,3-dienyl]-dimethylsilane
• CAS: 857350-07-3
• 化学式: C₂₀H₂₄OSi
• 分子量: 308.495
• InChiKey: DVCTVRPZCIPHJW-IAGJPELUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.29
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E,E)-[4-(4-methoxyphenyl)-1,3-butadienyl]dimethylbenzylsilane 、 对碘苯甲酸乙酯 在 四丁基氟化铵 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以88%的产率得到ethyl (E,E)-4-[4-(4-methoxyphenyl)-1,3-butadienyl]benzoate
  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
• 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 61.0h， 生成 (E,E)-[4-(4-methoxyphenyl)-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.