3-methoxy-2-phenyl-4-(p-trifluoromethylphenyl)thiophene | 1192181-95-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-methoxy-2-phenyl-4-(p-trifluoromethylphenyl)thiophene
• 英文别名: 3-Methoxy-2-phenyl-4-[4-(trifluoromethyl)phenyl]thiophene
• CAS: 1192181-95-5
• 化学式: C₁₈H₁₃F₃OS
• 分子量: 334.362
• InChiKey: XLVHHIKMISTBHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  37.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-碘甲苯 、 3-methoxy-2-phenyl-4-(p-trifluoromethylphenyl)thiophene 在 2,2'-联吡啶 、 silver carbonate 、 palladium dichloride 作用下， 以 间二甲苯 为溶剂， 反应 12.0h， 以70%的产率得到3-methoxy-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：

  3-methoxy-2-phenylthiophene 、 4-碘三氟甲苯 在 三(1,1,1,3,3,3-六氟-2-丙基)亚磷酸 、 silver carbonate 、 palladium dichloride 作用下， 以 间二甲苯 为溶剂， 反应 22.0h， 生成 3-methoxy-2-pheny-4-(p-trifluoromethylphenyl)thiophene 、 3-methoxy-2-phenyl-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