<5-(3-bromophenyl)pyrazol-3-yl>acetonitrile | 202129-59-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: <5-(3-bromophenyl)pyrazol-3-yl>acetonitrile
• 英文别名: 3-cyanomethyl-5-(3-bromophenyl)pyrazole；2-[3-(3-bromophenyl)-1H-pyrazol-5-yl]acetonitrile
• CAS: 202129-59-7
• 化学式: C₁₁H₈BrN₃
• 分子量: 262.109
• InChiKey: RNJJKHRXHOULEM-UHFFFAOYSA-N

物化性质

• 沸点：
  463.0±35.0 °C(Predicted)
• 密度：
  1.554±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  52.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  <5-(3-bromophenyl)pyrazol-3-yl>acetonitrile 在 sodium t-butanolate 作用下， 以 乙醇 为溶剂， 反应 49.0h， 生成 (E)-2-<5-(3-bromophenyl)pyrazol-3-yl>-3-(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：

  3-cyano-4-thiomethyl-6-(3-bromophenyl)-2H-pyran-2-one 在 一水合肼 作用下， 以 甲醇 为溶剂， 以40%的产率得到<5-(3-bromophenyl)pyrazol-3-yl>acetonitrile
  参考文献：
  名称：

  Parmar, Virinder S.; Jain, Subhash C.; Jha, Amitabh, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1997, vol. 36, # 10, p. 872 - 879

  摘要：

  DOI：

文献信息

• (<i>E</i>)-2-[5-(3-Bromophenyl)pyrazol-3-yl]-3-(pyrrol-2-yl)acrylonitrile
  作者：A. Kumar、V. S. Parmar、W. Errington

  DOI：10.1107/s0108270198013067

  日期：1999.3.15

  The title compound, C16H11BrN4, has been isolated as its E isomer via the condensation of pyrrole-2-carboxaldehyde onto the active methylene of [5-(3-bromophenyl)pyrazol-3-yl]acetonitrile. It exhibits both intra- and intermolecular hydrogen bonding; the latter produces infinite one-dimensional chains of molecules.