N-(4-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)phenyl)-2,3,3-trichloroacrylamide | 1101891-14-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-(4-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)phenyl)-2,3,3-trichloroacrylamide
• CAS: 1101891-14-8
• 化学式: C₁₄H₆Cl₃F₆N₃O
• 分子量: 452.571
• InChiKey: WJJUULWJQQHJDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.73
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  46.92
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  3,5-bis(trifluoromethyl)-1-(4-nitrophenyl)pyrazole 在 palladium 10% on activated carbon 、 环己烯 、 三氯化磷 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 0.16h， 生成 N-(4-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)phenyl)-2,3,3-trichloroacrylamide
  参考文献：
  名称：

  Microwave-Assisted and Continuous Flow Multistep Synthesis of 4-(Pyrazol-1-yl)carboxanilides

  摘要：

  A series of 4-(pyrazol-1-yl)carboxanilides active as inhibitors of canonical transient receptor potential channels were synthesized in an efficient three-step protocol using controlled microwave heating. The general synthetic strategy involves condensation of 4-nitrophenylhydrazine with appropriate 1,3-dicarbonyl building blocks, followed by reduction of the nitro group to the amine, which is then amidated with carboxylic acids. Compared to the conventional protocol a dramatic reduction in overall processing time from similar to 2 days to a few minutes was achieved, accompanied by significantly improved product yields. In addition, the first two steps in the synthetic pathway were also performed under continuous flow conditions providing similar isolated product yields. As an alternative to the three-step protocol, a novel two-step route to the desired 4-(pyrazol-1-yl)carboxanilides was devised involving condensation of 4-bromophenylhydrazine with appropriate 1,3-dicarbonyl building blocks, followed by Pd-catalyzed Buchwald-Hartwig amidation with carboxylic acid amides.

  DOI：

  10.1021/jo2009824