2-methyl-3-(2-nitrophenyl)quinoxaline | 1426682-60-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-methyl-3-(2-nitrophenyl)quinoxaline
• CAS: 1426682-60-1
• 化学式: C₁₅H₁₁N₃O₂
• 分子量: 265.271
• InChiKey: YANANSVSVNQFPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  68.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  1-(2'-硝基苯基)-2-硝基丙-1-烯 、 邻苯二胺 在 copper(ll) bromide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以38%的产率得到2-methyl-3-(2-nitrophenyl)quinoxaline
  参考文献：
  名称：

  Cu(II)-catalyzed synthesis of quinoxalines from o-phenylenediamines and nitroolefins

  摘要：

  An easy and efficient copper-catalyzed reaction for the synthesis of quinoxalines from o-phenylenediamines and nitroolefins is developed. This reaction could proceed well without additional base and be applied to various available substrates with a one-step synthetic procedure in moderate to good yields. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.11.127

文献信息

• Chemoselective synthesis of quinoxalines and benzimidazoles by silica gel catalysis
  作者：Chunmei Li、Furen Zhang、Zhen Yang、Chenze Qi

  DOI：10.1016/j.tetlet.2014.08.022

  日期：2014.10

  Treatment of nitroolefins and o-phenylenediamine with silica gel catalyst produced quinoxalines mainly in THF, but gave benzimidazoles efficiently in water. Such a solvent-dependent chemoselective reaction has prominent features of affording two cyclized products selectively with the same substrate, short reaction time, operational simplicity, as well as available starting materials and nontoxic catalysts. In addition, the scope and limitations were explored and a plausible reaction mechanism is proposed. (C) 2014 Elsevier Ltd. All rights reserved.