1-(n-butyl)-3-benzoylquinoxalin-2(1H)-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(n-butyl)-3-benzoylquinoxalin-2(1H)-one
• 英文别名: 1-n-butyl-3-benzoylquinoxalin-2-one；3-Benzoyl-1-butyl-1H-quinoxalin-2-one；3-benzoyl-1-butylquinoxalin-2-one
• 化学式: C₁₉H₁₈N₂O₂
• 分子量: 306.364
• InChiKey: CMXVODXHPCNOJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  49.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(n-butyl)-3-benzoylquinoxalin-2(1H)-one 在 对甲苯磺酸 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 13.0h， 生成 C₂₃H₁₈N₆
  参考文献：
  名称：

  An efficient metal-free synthesis of 2-(pyrazin-2-yl)benzimidazoles from quinoxalinones and diaminomaleonitrile via a novel rearrangement

  摘要：

  A simple and highly efficient metal-free method for the synthesis of 2-(pyrazin-2-yl)benzimidazoles has been developed on the basis of the novel ring contraction of 3-aroyl- and 3-alkanoyiquinoxalin-2-ones with diaminomaleonitrile. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.013
• 作为产物：
  描述：

  2-羟基喹喔啉 在 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺-d7 、 二甲基亚砜 为溶剂， 生成 1-(n-butyl)-3-benzoylquinoxalin-2(1H)-one
  参考文献：
  名称：

  Metal- and Photocatalyst-Free Approach to Visible-Light-Induced Acylation of Quinoxalinones.

  摘要：

  A transition-metal- and photocatalyst-free photochemical reaction was successfully developed for the direct acylation of quinoxalin-2(1H)-ones, which was enabled by the formation of electron donor-acceptor (EDA) complexes. The use of DBU...

  DOI：

  10.1039/d4ob00630e

文献信息

• A simple and efficient method for the synthesis of highly substituted imidazoles using 3-aroylquinoxalin-2(1H)-ones
  作者：Vakhid A. Mamedov、Nataliya A. Zhukova、Tat′yana N. Beschastnova、Aidar T. Gubaidullin、Dimitry V. Rakov、Il’dar Kh. Rizvanov

  DOI：10.1016/j.tetlet.2011.06.014

  日期：2011.8

  analogues of α-diketones for the efficient, one-pot, three component synthesis of 2,4,5-trisubstituted imidazoles and imidazo[1,5-a]quinoxalin-4(5H)-ones in boiling methanol. The key advantages of this process are high yields, ready availability and low cost of 3-aroylquinoxalin-2(1H)-ones and easy work-up and separation of the products by non-chromatographic methods. Furthermore, the presence of an

  发现3-Aroylquinoxalin-2（1 H）-ones是α-二酮的杂类似物，可高效，一锅，三组分合成2,4,5-三取代的咪唑和咪唑[1,5- a ]喹喔啉-4（5 H）-在沸腾的甲醇中的混合物。该方法的主要优点是高产率，3-芳基喹喔啉-2（1 H）-1的易得性和低成本以及通过非色谱法易于处理和分离产物的能力。此外，在获得的咪唑的4位上存在邻-亚氨基苯胺片段使得以几乎定量的产率生产2-（咪唑-4-基）苯并咪唑成为可能。
• Ring contraction in reactions of 3-benzoylquinoxalin-2-ones with 1,2-phenylenediamines. Quinoxaline-benzoimidazole rearrangement
  作者：V. A. Mamedov、A. A. Kalinin、A. T. Gubaidullin、A. V. Chernova、I. A. Litvinov、Ya. A. Levin、R. R. Shagidullin

  DOI：10.1023/b:rucb.0000024846.27508.76

  日期：2004.1

  The reactions of 3-benzoylquinoxalin-2-one and its N(1)-alkyl derivatives with 1,2-phenylenediamines were accompanied by ring contraction as a result of the quinoxaline-benzoimidazole rearrangement giving rise to 2-benzoimidazolyl-substituted quinoxalines. The possible pathways of these reaction are discussed.

  3-苯甲酰基喹喔啉-2-one 及其 N(1)-烷基衍生物与 1,2-苯二胺的反应伴随着环收缩，这是由于喹喔啉-苯并咪唑重排产生 2-苯并咪唑基取代喹喔啉的结果。讨论了这些反应的可能途径。
• An efficient metal-free synthesis of 2-(pyrazin-2-yl)benzimidazoles from quinoxalinones and diaminomaleonitrile via a novel rearrangement
  作者：Vakhid A. Mamedov、Nataliya A. Zhukova、Tat′yana N. Beschastnova、El’vira I. Zakirova、Saniya F. Kadyrova、Ekaterina V. Mironova、Anna G. Nikonova、Shamil K. Latypov、Igor A. Litvinov

  DOI：10.1016/j.tetlet.2011.11.013

  日期：2012.1

  A simple and highly efficient metal-free method for the synthesis of 2-(pyrazin-2-yl)benzimidazoles has been developed on the basis of the novel ring contraction of 3-aroyl- and 3-alkanoyiquinoxalin-2-ones with diaminomaleonitrile. (C) 2011 Elsevier Ltd. All rights reserved.
• Metal- and Photocatalyst-Free Approach to Visible-Light-Induced Acylation of Quinoxalinones.
  作者：Worawat Niwetmarin、Naiyana Saesian、Rungroj Saruengkhanphasit、Chatchakorn Eurtivong、Nopporn Thasana、Somsak Ruchirawat

  DOI：10.1039/d4ob00630e

  日期：——

  A transition-metal- and photocatalyst-free photochemical reaction was successfully developed for the direct acylation of quinoxalin-2(1H)-ones, which was enabled by the formation of electron donor-acceptor (EDA) complexes. The use of DBU...