(2,3,4,5,6-Pentafluorophenyl) 5-[2-(4-methylphenyl)ethynyl]thiophene-2-sulfonate | 1414882-00-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: (2,3,4,5,6-Pentafluorophenyl) 5-[2-(4-methylphenyl)ethynyl]thiophene-2-sulfonate
• CAS: 1414882-00-0
• 化学式: C₁₉H₉F₅O₃S₂
• 分子量: 444.403
• InChiKey: NGQYEZRKWOQHKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  80
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2,3,4,5,6-Pentafluorophenyl) 5-[2-(4-methylphenyl)ethynyl]thiophene-2-sulfonate 、 methyl (2R)-2-amino-3-(1H-indol-2-yl)propanoate 在 吡啶 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 18.0h， 以78%的产率得到
  参考文献：
  名称：

  100 Gram Scale Synthesis of a Key Intermediate of Matrix Metalloproteinase Inhibitor in a Continuous-Flow System Based on a Copper-Free Sonogashira Reaction Using an Ionic Liquid as a Catalyst Support

  摘要：

  The key intermediate of matrix metalloproteinase (MMP) inhibitor was synthesized using a flow microreactor for a copper-free Sonogashira coupling reaction in an ionic liquid. The ionic liquid [emim]NTf2 was used as a solvent and a catalyst support. A 100 g scale synthesis was achieved in combination with a flow-extraction/catalyst-recycling system, in which the ionic liquid containing the palladium catalyst was continuously recycled.

  DOI：

  10.1055/s-0031-1290456
• 作为产物：
  描述：

  2,3,4,5,6-Pentafluorophenyl 5-bromo-2-thiophenesulfonate 、 4-甲苯基乙炔 在 C₂₆H₃₀Cl₂N₂PPd 、 potassium carbonate 、 二异丙胺 、 1-乙基-3-甲基咪唑啉双(三氟甲基磺酰基)亚胺 作用下， 以 水 为溶剂， 反应 5.5h， 以86%的产率得到(2,3,4,5,6-Pentafluorophenyl) 5-[2-(4-methylphenyl)ethynyl]thiophene-2-sulfonate
  参考文献：
  名称：

  100 Gram Scale Synthesis of a Key Intermediate of Matrix Metalloproteinase Inhibitor in a Continuous-Flow System Based on a Copper-Free Sonogashira Reaction Using an Ionic Liquid as a Catalyst Support

  摘要：

  The key intermediate of matrix metalloproteinase (MMP) inhibitor was synthesized using a flow microreactor for a copper-free Sonogashira coupling reaction in an ionic liquid. The ionic liquid [emim]NTf2 was used as a solvent and a catalyst support. A 100 g scale synthesis was achieved in combination with a flow-extraction/catalyst-recycling system, in which the ionic liquid containing the palladium catalyst was continuously recycled.

  DOI：

  10.1055/s-0031-1290456