2-甲基-3-(4-硝基苯基)喹喔啉 | 6158-99-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 2-甲基-3-(4-硝基苯基)喹喔啉
• 英文名称: 2-methyl-3-(4-nitrophenyl)quinoxaline
• 英文别名: 2-methyl-3-(4-nitro-phenyl)-quinoxaline；2-Methyl-3-(4-nitro-phenyl)-chinoxalin；2-Methyl-3--chinoxalin；2-(p-Nitrophenyl)-3-methylchinoxalin
• CAS: 6158-99-2
• 化学式: C₁₅H₁₁N₃O₂
• 分子量: 265.271
• InChiKey: JPDRJECJACBTTE-UHFFFAOYSA-N

物化性质

• 熔点：
  137-138 °C
• 沸点：
  417.9±40.0 °C(Predicted)
• 密度：
  1.304±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  71.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(p-nitrophenyl)-2-nitro-1-propene 、 邻苯二胺 在 silica gel 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以71%的产率得到2-甲基-3-(4-硝基苯基)喹喔啉
  参考文献：
  名称：

  Chemoselective synthesis of quinoxalines and benzimidazoles by silica gel catalysis

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2014.08.022

文献信息

• DABCO-Catalyzed Oxidation of Deoxybenzoins to Benzils with Air and One-Pot Synthesis of Quinoxalines
  作者：Huanfeng Jiang、Chaorong Qi、Liangbin Huang、Zhengwang Chen、Huoji Chen

  DOI：10.1055/s-0030-1258375

  日期：2011.2

  Aerobic oxidation of deoxybenzoins could be efficiently catalyzed by 1,4-diazabicyclo[2.2.2]octane (DABCO) with air as the sole oxidant to give the corresponding benzils in excellent yields. The effects of reaction conditions, such as different bases, temperature, time and solvent, on the yield of the product were investigated. Moreover, the process has been successfully extended to a one-pot synthesis of quinoxalines from benzyl ketones and aromatic 1,2-diamines.

  脱氧苯酮的好氧氧化可以通过1,4-二氮杂双环[2.2.2]八烷（DABCO）高效催化，以空气作为唯一氧化剂，获得相应的苯基酮，产率极高。研究了反应条件（如不同的碱、温度、时间和溶剂）对产物产率的影响。此外，该过程已成功扩展至从苯基酮和芳香性1,2-二胺一锅合成喹唑啉。
• Sicher et al., Collection of Czechoslovak Chemical Communications, 1954, vol. 19, p. 317,327
  作者：Sicher et al.

  DOI：——

  日期：——
• Alberti et al., Gazzetta Chimica Italiana, 1953, vol. 83, p. 922,924
  作者：Alberti et al.

  DOI：——

  日期：——
• Cu(II)-catalyzed synthesis of quinoxalines from o-phenylenediamines and nitroolefins
  作者：Yongxin Chen、Kangning Li、Mingming Zhao、Yuanjiao Li、Baohua Chen

  DOI：10.1016/j.tetlet.2012.11.127

  日期：2013.3

  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.
• 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.