(E)-2-bromo-1-methyl-4-nitro-5-styryl-1H-imidazole | 1456787-32-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (E)-2-bromo-1-methyl-4-nitro-5-styryl-1H-imidazole
• 英文别名: 2-bromo-1-methyl-4-nitro-5-[(E)-2-phenylethenyl]imidazole
• CAS: 1456787-32-8
• 化学式: C₁₂H₁₀BrN₃O₂
• 分子量: 308.134
• InChiKey: OEIJZQKGNBXKOP-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  63.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  zinc(II) cyanide 、 (E)-2-bromo-1-methyl-4-nitro-5-styryl-1H-imidazole 在 1,1'-双(二苯基膦)二茂铁 、 tris-(dibenzylideneacetone)dipalladium(0) 、 锌 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 1.0h， 以82%的产率得到(E)-1-methyl-4-nitro-5-styryl-1H-imidazole-2-carbonitrile
  参考文献：
  名称：

  Synthesis of substituted 5-bromomethyl-4-nitroimidazoles and use for the preparation of the hypoxia-selective multikinase inhibitor SN29966

  摘要：

  5-Bromomethyl-4-nitroimidazoles have utility as bioreductive trigger precursors for the preparation of hypoxia-selective prodrugs. Here we describe an efficient two-step synthesis of 5-(bromomethyl)-1-methyl-4-nitro-1H-imidazole, a preferred precursor, employing an N-bromosuccinimide mediated radical bromination. Use of this precursor to prepare SN29966, a promising hypoxia-selective irreversible pan-ErbB inhibitor is reported along with the preparation of four other prodrug candidates. 5-Bromomethyl-4-nitroimidazole analogues bearing electron-donating and electron-withdrawing substituents at the N-1 and C-2 positions are also described. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.08.037
• 作为产物：
  描述：

  1,5-二甲基-4-硝基咪唑 在 哌啶 、 溴 作用下， 以 氯仿 为溶剂， 反应 16.0h， 生成 (E)-2-bromo-1-methyl-4-nitro-5-styryl-1H-imidazole
  参考文献：
  名称：

  Synthesis of substituted 5-bromomethyl-4-nitroimidazoles and use for the preparation of the hypoxia-selective multikinase inhibitor SN29966

  摘要：

  5-Bromomethyl-4-nitroimidazoles have utility as bioreductive trigger precursors for the preparation of hypoxia-selective prodrugs. Here we describe an efficient two-step synthesis of 5-(bromomethyl)-1-methyl-4-nitro-1H-imidazole, a preferred precursor, employing an N-bromosuccinimide mediated radical bromination. Use of this precursor to prepare SN29966, a promising hypoxia-selective irreversible pan-ErbB inhibitor is reported along with the preparation of four other prodrug candidates. 5-Bromomethyl-4-nitroimidazole analogues bearing electron-donating and electron-withdrawing substituents at the N-1 and C-2 positions are also described. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.08.037