4-fluoro-1-methyl-3-phenyl-1H-pyrazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-fluoro-1-methyl-3-phenyl-1H-pyrazole
• 英文别名: 4-Fluoro-1-methyl-3-phenylpyrazole；4-fluoro-1-methyl-3-phenylpyrazole
• 化学式: C₁₀H₉FN₂
• 分子量: 176.193
• InChiKey: XFBJWFGFLVAABH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  氟三溴甲烷 、 benzaldehyde N,N-dimethylhydrazone 在 tris(triphenylphosphine)ruthenium(II) chloride 、 potassium carbonate 作用下， 以 二乙二醇二甲醚 为溶剂， 反应 15.0h， 以73%的产率得到4-fluoro-1-methyl-3-phenyl-1H-pyrazole
  参考文献：
  名称：

  Ruthenium-Catalyzed Tandem C–H Fluoromethylation/Cyclization of N-Alkylhydrazones with CBr₃F: Access to 4-Fluoropyrazoles

  摘要：

  4-Fluoropyrazoles are accessible in a single step from readily available aldehyde-derived N-alkylhydrazones through double C-H fluoroalkylation with tribromofluoromethane (CBr3F). RuCl2(PPh3)(3) has been proven to be the most efficient catalyst for this transformation when compared to a range of other Cu-, Pd-, or Fe-based catalyst systems.

  DOI：

  10.1021/acs.joc.7b00085

文献信息

• Reactions of 1-Substituted-polyfluoro-1-propenyl<i>p</i>-Toluenesulfonates with Bifunctional Nitrogen Nucleophiles. A New Expedient Access to Monofluorinated Nitrogen Heterocycles
  作者：Kazumasa Funabiki、Tetsuya Ohtsuki、Takashi Ishihara、Hiroki Yamanaka

  DOI：10.1246/cl.1995.239

  日期：1995.3

  1-Substituted-2,3,3-trifluoro-1-propenyl p-toluenesulfonates, readily available by the alkylation or arylation of 2,3,3-trifluoro-1-tosyloxy-1-propenyllithium or -zinc reagent, reacted smoothly with amidine or hydrazine derivatives at 70 °C for 1 h to give the corresponding 5-fluoropyrimidine or 4-fluoropyrazole compounds, respectively, in moderate to excellent yields.

  1-取代-2,3,3-三氟-1-丙烯基对甲苯磺酸盐，可通过2,3,3-三氟-1-甲苯磺氧基-1-丙烯基锂或锌试剂的烷基化或芳基化容易获得，与脒或肼衍生物在70℃下反应1小时，分别得到相应的5-氟嘧啶或4-氟吡唑化合物，产率中等至优异。
• Ruthenium-Catalyzed Tandem C–H Fluoromethylation/Cyclization of <i>N</i>-Alkylhydrazones with CBr₃F: Access to 4-Fluoropyrazoles
  作者：Alexis Prieto、Didier Bouyssi、Nuno Monteiro

  DOI：10.1021/acs.joc.7b00085

  日期：2017.3.17

  4-Fluoropyrazoles are accessible in a single step from readily available aldehyde-derived N-alkylhydrazones through double C-H fluoroalkylation with tribromofluoromethane (CBr3F). RuCl2(PPh3)(3) has been proven to be the most efficient catalyst for this transformation when compared to a range of other Cu-, Pd-, or Fe-based catalyst systems.