ethyl 5-(3-chlorophenyl)-4-iodo-1-methyl-1H-pyrazole-3-carboxylate | 1370022-90-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 5-(3-chlorophenyl)-4-iodo-1-methyl-1H-pyrazole-3-carboxylate
• 英文别名: Ethyl 5-(3-chlorophenyl)-4-iodo-1-methylpyrazole-3-carboxylate
• CAS: 1370022-90-4
• 化学式: C₁₃H₁₂ClIN₂O₂
• 分子量: 390.608
• InChiKey: GPVZCVYUSOTHPZ-UHFFFAOYSA-N

物化性质

• 沸点：
  456.9±45.0 °C(Predicted)
• 密度：
  1.70±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.52
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  44.12
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl 5-(3-chlorophenyl)-4-iodo-1-methyl-1H-pyrazole-3-carboxylate 、 2-甲基-3-丁炔-2-醇 在 copper(l) iodide 、 palladium 10% on activated carbon 、 三乙胺 、 三苯基膦 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以83%的产率得到ethyl 5-(3-chlorophenyl)-4-(3-hydroxy-3-methylbut-1-ynyl)-1-methyl-1H-pyrazole-3-carboxylate
  参考文献：
  名称：

  Design and synthesis of 4-alkynyl pyrazoles as inhibitors of PDE4: A practical access via Pd/C–Cu catalysis

  摘要：

  The design and synthesis of 4-alkynyl pyrazole derivatives has led to the identification of new class of PDE4 inhibitors. All these compounds were accessed for the first time via a facile Pd/C-CuI-PPh3 mediated C-C bond forming reaction between an appropriate pyrazole iodide and various terminal alkynes. In vitro PDE4B inhibitory properties and molecular modeling studies of some of the compounds synthesized indicated that 4-alkynyl pyrazole could be a promising template for the discovery of novel PDE4 inhibitors. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.02.008
• 作为产物：
  描述：

  3-氯苯乙酮 在 ammonium cerium (IV) nitrate 、 碘 、 sodium 、 溶剂黄146 、 potassium hydroxide 、 肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 33.33h， 生成 ethyl 5-(3-chlorophenyl)-4-iodo-1-methyl-1H-pyrazole-3-carboxylate
  参考文献：
  名称：

  Design and synthesis of 4-alkynyl pyrazoles as inhibitors of PDE4: A practical access via Pd/C–Cu catalysis

  摘要：

  The design and synthesis of 4-alkynyl pyrazole derivatives has led to the identification of new class of PDE4 inhibitors. All these compounds were accessed for the first time via a facile Pd/C-CuI-PPh3 mediated C-C bond forming reaction between an appropriate pyrazole iodide and various terminal alkynes. In vitro PDE4B inhibitory properties and molecular modeling studies of some of the compounds synthesized indicated that 4-alkynyl pyrazole could be a promising template for the discovery of novel PDE4 inhibitors. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.02.008