3,4-bistrimethylsilylethynyl-1-phenylpyrazole | 1242028-55-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3,4-bistrimethylsilylethynyl-1-phenylpyrazole
• 英文别名: Trimethyl-[2-[1-phenyl-3-(2-trimethylsilylethynyl)pyrazol-4-yl]ethynyl]silane
• CAS: 1242028-55-2
• 化学式: C₁₉H₂₄N₂Si₂
• 分子量: 336.584
• InChiKey: MMASQUKYVJXXDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.33
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,4-bistrimethylsilylethynyl-1-phenylpyrazole 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以99%的产率得到3,4-diethynyl-1-phenylpyrazole
  参考文献：
  名称：

  Microwave-Assisted Selective Synthesis of 2H-Indazoles via Double Sonogashira Coupling of 3,4-Diiodopyrazoles and Bergman–Masamune Cycloaromatization

  摘要：

  The microwave-assisted double Sonogashira coupling of 3,4-diiodo-1-trityl and 1-phenylpyrazole with terminal acetylene took only three minutes. Dialkynylpyrazoles, the coupling products, were heated at 240 degrees C in the presence of 1,4-cyclohexadiene to obtain 2H-2-trityl and 2-phenylindazoles, respectively. This synthetic route to 2H-indazole, which was achieved via cyclization to form the 6-membered ring of dialkynylpyrazole, is a novel procedure.

  DOI：

  10.3987/com-10-11950
• 作为产物：
  描述：

  3,4-diiodo-1-phenylpyrazole 、 三甲基乙炔基硅 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.05h， 以90%的产率得到3,4-bistrimethylsilylethynyl-1-phenylpyrazole
  参考文献：
  名称：

  Microwave-Assisted Selective Synthesis of 2H-Indazoles via Double Sonogashira Coupling of 3,4-Diiodopyrazoles and Bergman–Masamune Cycloaromatization

  摘要：

  The microwave-assisted double Sonogashira coupling of 3,4-diiodo-1-trityl and 1-phenylpyrazole with terminal acetylene took only three minutes. Dialkynylpyrazoles, the coupling products, were heated at 240 degrees C in the presence of 1,4-cyclohexadiene to obtain 2H-2-trityl and 2-phenylindazoles, respectively. This synthetic route to 2H-indazole, which was achieved via cyclization to form the 6-membered ring of dialkynylpyrazole, is a novel procedure.

  DOI：

  10.3987/com-10-11950