2-phenyl-5-(p-tolyl)-4-(p-trifluoromethylphenyl)thiophene-3-yl trifluoromethanesulfonate | 1192182-04-9

• 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: 2-phenyl-5-(p-tolyl)-4-(p-trifluoromethylphenyl)thiophene-3-yl trifluoromethanesulfonate
• CAS: 1192182-04-9
• 化学式: C₂₅H₁₆F₆O₃S₂
• 分子量: 542.523
• InChiKey: VXSIMFFNGCHBDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  36.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-phenyl-5-(p-tolyl)-4-(p-trifluoromethylphenyl)thiophene-3-yl trifluoromethanesulfonate 、 4-甲氧基苯硼酸 在 四(三苯基膦)钯 、 barium(II) hydroxide 作用下， 以 水 、 正丁醇 为溶剂， 反应 15.0h， 以74%的产率得到3-(p-methoxyphenyl)-2-phenyl-5-(p-tolyl)-4-(p-trifluoromethylphenyl)thiophene
  参考文献：
  名称：

  Programmed Synthesis of Tetraarylthiophenes through Sequential C−H Arylation

  摘要：

  A general protocol for the programmed synthesis of tetraarylthiophenes has been established. The utilization of three catalysts, RhCl(CO){P[OCH(CF3)(2)](3)}(2), PdCl2/P[OCH(CF3)(2)](3), and PdCl2/bipy, enables regioselective sequential arylations at the three C-H bonds of 3-methoxythiophene with iodoarenes. Interesting metal- and ligand-controlled regiodivergent: C-H arylations have been uncovered during this study. The installation of fourth aryl groups to the thus-generated 2,4,5-triaryl-3-methoxythiophenes has been accomplished through a sequence of demethylation, triflation, and Suzuki-Miyaura coupling.

  DOI：

  10.1021/ja906215b
• 作为产物：
  描述：

  三氟甲磺酸酐 、 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-phenyl-5-(p-tolyl)-4-(p-trifluoromethylphenyl)thiophene-3-yl trifluoromethanesulfonate
  参考文献：
  名称：

  Programmed Synthesis of Tetraarylthiophenes through Sequential C−H Arylation

  摘要：

  A general protocol for the programmed synthesis of tetraarylthiophenes has been established. The utilization of three catalysts, RhCl(CO){P[OCH(CF3)(2)](3)}(2), PdCl2/P[OCH(CF3)(2)](3), and PdCl2/bipy, enables regioselective sequential arylations at the three C-H bonds of 3-methoxythiophene with iodoarenes. Interesting metal- and ligand-controlled regiodivergent: C-H arylations have been uncovered during this study. The installation of fourth aryl groups to the thus-generated 2,4,5-triaryl-3-methoxythiophenes has been accomplished through a sequence of demethylation, triflation, and Suzuki-Miyaura coupling.

  DOI：

  10.1021/ja906215b