3,4-Dibutoxy-2-methyl-5-(2,3,4,5,6-pentafluorophenyl)thiophene | 881000-97-1

• 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: 3,4-Dibutoxy-2-methyl-5-(2,3,4,5,6-pentafluorophenyl)thiophene
• CAS: 881000-97-1
• 化学式: C₁₉H₂₁F₅O₂S
• 分子量: 408.433
• InChiKey: IWJCQFKOJNMYEW-UHFFFAOYSA-N

物化性质

• 沸点：
  367.8±37.0 °C(Predicted)
• 密度：
  1.243±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  46.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,4-dibutyloxy-2,5-bis(trimethylsilyl)thiophene 、 3,4-Dibutoxy-2-methyl-5-(2,3,4,5,6-pentafluorophenyl)thiophene 在 18-冠醚-6 、 cesium fluoride 作用下， 以 甲苯 为溶剂， 以74%的产率得到C₅₀H₆₀F₈O₆S₃
  参考文献：
  名称：

  Transition-Metal-Free Synthesis of Alternating Thiophene−Perfluoroarene Copolymers

  摘要：

  The fluoride-activated coupling between silyl-functionalized thiophene monomers and perfluoroarenes leads to moderately high-molecular-weight alternating copolymers in excellent yields and high chemical purity. The method bypasses transition-metal catalysis and the associated need for perfluoroarenes carrying additional functional "handles". Small-molecule model studies provide insight into the relative reactivities of functional groups in this synthetic pathway.

  DOI：

  10.1021/ja056074y
• 作为产物：
  描述：

  3,4-di-n-butoxythiophene 在 正丁基锂 、 18-冠醚-6 、 cesium fluoride 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 2.0h， 生成 3,4-Dibutoxy-2-methyl-5-(2,3,4,5,6-pentafluorophenyl)thiophene
  参考文献：
  名称：

  Transition-Metal-Free Synthesis of Alternating Thiophene−Perfluoroarene Copolymers

  摘要：

  The fluoride-activated coupling between silyl-functionalized thiophene monomers and perfluoroarenes leads to moderately high-molecular-weight alternating copolymers in excellent yields and high chemical purity. The method bypasses transition-metal catalysis and the associated need for perfluoroarenes carrying additional functional "handles". Small-molecule model studies provide insight into the relative reactivities of functional groups in this synthetic pathway.

  DOI：

  10.1021/ja056074y

文献信息

• Transition metal free coupling of highly fluorinated and non-fluorinated pi-electron systems
  申请人：Watson Mark D.

  公开号：US20080042127A1

  公开（公告）日：2008-02-21

  A method for making an organic conjugated monomer, oligomer, polymer or small molecule includes reacting a silyl substituted pi-system compound with a highly fluorinated pi-system compound.
• Transition-Metal-Free Synthesis of Alternating Thiophene−Perfluoroarene Copolymers
  作者：Yongfeng Wang、Mark D. Watson

  DOI：10.1021/ja056074y

  日期：2006.3.1

  The fluoride-activated coupling between silyl-functionalized thiophene monomers and perfluoroarenes leads to moderately high-molecular-weight alternating copolymers in excellent yields and high chemical purity. The method bypasses transition-metal catalysis and the associated need for perfluoroarenes carrying additional functional "handles". Small-molecule model studies provide insight into the relative reactivities of functional groups in this synthetic pathway.