(E)-butyl 3-(3-(difluoromethyl)-5-(4-fluorophenyl)-1-(4-methoxyphenyl)-1H-pyrazol-4-yl)acrylate | 1448155-49-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (E)-butyl 3-(3-(difluoromethyl)-5-(4-fluorophenyl)-1-(4-methoxyphenyl)-1H-pyrazol-4-yl)acrylate
• 英文别名: butyl (E)-3-[3-(difluoromethyl)-5-(4-fluorophenyl)-1-(4-methoxyphenyl)pyrazol-4-yl]prop-2-enoate
• CAS: 1448155-49-4
• 化学式: C₂₄H₂₃F₃N₂O₃
• 分子量: 444.453
• InChiKey: KXESBYCXJYTXQH-BUHFOSPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  53.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  丙烯酸丁酯 、 3-(difluoromethyl)-5-(4-fluorophenyl)-1-(4-methoxyphenyl)-1H-pyrazole 在 palladium diacetate 、 silver carbonate 、 对苯醌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以52%的产率得到(E)-butyl 3-(3-(difluoromethyl)-5-(4-fluorophenyl)-1-(4-methoxyphenyl)-1H-pyrazol-4-yl)acrylate
  参考文献：
  名称：

  A new and direct route to 3-fluoromethyl substituted pyrazol-4-acrylates via Pd-catalyzed C–H activation

  摘要：

  Direct C4-H activation of 3-fluoromethyl pyrazoles followed by an oxidative coupling with acrylates, which is perhaps the most direct method for the synthesis of 3-fluoromethyl substituted pyrazol-4-aciylates of biological interest, remains challenging. Here, the first example of the straightforward olefination via Pd-catalyzed C4-H activation of both C3-CF3 and C3-CF2H substituted pyrazoles is reported. The reaction of various C3-CF3 substituted pyrazoles with acrylates proceeds smoothly in the presence of Pd(OAc)(2) and Ag2CO3, whereas olefination of C3-CF2H substituted pyrazoles requires the addition of benzoquinone. A further computational study reveals that reactivity of the pyrazolyl substrates employed are strongly impacted by the substituents of different nature on their C1 or C5 position, which is in good agreement with the experimental data. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.06.058

文献信息

• A new and direct route to 3-fluoromethyl substituted pyrazol-4-acrylates via Pd-catalyzed C–H activation
  作者：Xiaoguang Wang、Xiang Fang、Hongyuan Xiao、Dongming Gong、Xueyan Yang、Fanhong Wu

  DOI：10.1016/j.tet.2013.06.058

  日期：2013.8

  Direct C4-H activation of 3-fluoromethyl pyrazoles followed by an oxidative coupling with acrylates, which is perhaps the most direct method for the synthesis of 3-fluoromethyl substituted pyrazol-4-aciylates of biological interest, remains challenging. Here, the first example of the straightforward olefination via Pd-catalyzed C4-H activation of both C3-CF3 and C3-CF2H substituted pyrazoles is reported. The reaction of various C3-CF3 substituted pyrazoles with acrylates proceeds smoothly in the presence of Pd(OAc)(2) and Ag2CO3, whereas olefination of C3-CF2H substituted pyrazoles requires the addition of benzoquinone. A further computational study reveals that reactivity of the pyrazolyl substrates employed are strongly impacted by the substituents of different nature on their C1 or C5 position, which is in good agreement with the experimental data. (C) 2013 Elsevier Ltd. All rights reserved.