(Z)-2-[5-(4-Bromo-phenyl)-1H-pyrazol-3-yl]-3-(1H-pyrrol-2-yl)-acrylonitrile | 244216-80-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (Z)-2-[5-(4-Bromo-phenyl)-1H-pyrazol-3-yl]-3-(1H-pyrrol-2-yl)-acrylonitrile
• CAS: 244216-80-6
• 化学式: C₁₆H₁₁BrN₄
• 分子量: 339.194
• InChiKey: OLHCJOQAUVBAAP-XYOKQWHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.23
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68.26
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (Z)-2-[5-(4-Bromo-phenyl)-1H-pyrazol-3-yl]-3-(1H-pyrrol-2-yl)-acrylonitrile 在 sodium t-butanolate 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 (E)-2-[5-(4-Bromo-phenyl)-1H-pyrazol-3-yl]-3-(1H-pyrrol-2-yl)-acrylonitrile
  参考文献：
  名称：

  Synthesis of E - and Z -Pyrazolylacrylonitriles and their evaluation as novel antioxidants

  摘要：

  A facile synthesis of (Z)- and (E)-2-(5-arylpyrazol-3-yl)-3-(pyrrol-2-yl)acrylonitriles and (Z)-2-(1,3-diarylpyrazol-5-yl)-3-(pyrrol-2-yl)acrylonitriles, and isomerisation of (Z)-2-(5-arylpyrazolyl)acrylonitriles to (E)-2-(5-arylpyrazolyl)acrylonitriles under basic conditions have been reported. (Z)-2-(1,3-Diarylpyrazolyl)acrylonitrile did not undergo isomerisation under the similar conditions. New compounds were identified on the basis of their spectral data (H-1-, C-13-, H-1-H-1 COSY, NOESY, NOE, HMQC NMR, IR, UV and EI mass). The structures of one acrylonitrile and five of their precursor 6-arylpyran-2-ones and cyanomethylpyrazoles were confirmed by X-ray crystallographic studies. Effects of pyrazolylacrylonitriles and their precursors on rat liver-microsomal lipid peroxidation were evaluated in vitro with a view to establish structure-activity relationship and to identify a lead compound. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00056-5
• 作为产物：
  描述：

  2-吡咯甲醛 、 2-(5-(4-bromophenyl)-1H-pyrazol-3-yl)acetonitrile 在 sodium t-butanolate 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以91%的产率得到(Z)-2-[5-(4-Bromo-phenyl)-1H-pyrazol-3-yl]-3-(1H-pyrrol-2-yl)-acrylonitrile
  参考文献：
  名称：

  Synthesis of E - and Z -Pyrazolylacrylonitriles and their evaluation as novel antioxidants

  摘要：

  A facile synthesis of (Z)- and (E)-2-(5-arylpyrazol-3-yl)-3-(pyrrol-2-yl)acrylonitriles and (Z)-2-(1,3-diarylpyrazol-5-yl)-3-(pyrrol-2-yl)acrylonitriles, and isomerisation of (Z)-2-(5-arylpyrazolyl)acrylonitriles to (E)-2-(5-arylpyrazolyl)acrylonitriles under basic conditions have been reported. (Z)-2-(1,3-Diarylpyrazolyl)acrylonitrile did not undergo isomerisation under the similar conditions. New compounds were identified on the basis of their spectral data (H-1-, C-13-, H-1-H-1 COSY, NOESY, NOE, HMQC NMR, IR, UV and EI mass). The structures of one acrylonitrile and five of their precursor 6-arylpyran-2-ones and cyanomethylpyrazoles were confirmed by X-ray crystallographic studies. Effects of pyrazolylacrylonitriles and their precursors on rat liver-microsomal lipid peroxidation were evaluated in vitro with a view to establish structure-activity relationship and to identify a lead compound. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00056-5