3-phenylacetylquinoxaline-2(1H)-one | 101291-14-9

• 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: 3-phenylacetylquinoxaline-2(1H)-one
• 英文别名: 3-phenylacetylquinoxalin-2(1H)-one；3-phenylacetylquinoxaline-2(1H)one；3-phenylacetyl-1H-quinoxalin-2-one；3-Phenylacetyl-1H-chinoxalin-2-on；3-(2-phenylacetyl)-1H-quinoxalin-2-one
• CAS: 101291-14-9
• 化学式: C₁₆H₁₂N₂O₂
• 分子量: 264.283
• InChiKey: VGIHQGGRFCZOJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  58.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-phenylacetylquinoxaline-2(1H)-one 在 硫酸 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 2.17h， 生成 C₂₀H₁₂N₆
  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：

  3-(α,β-dibromo-phenethyl)-1H-quinoxalin-2-one 在 乙醇 、 potassium acetate 作用下， 生成 3-phenylacetylquinoxaline-2(1H)-one
  参考文献：
  名称：

  Bodforss, Justus Liebigs Annalen der Chemie, 1957, vol. 609, p. 103,117

  摘要：

  DOI：

文献信息

• A new facile, efficient synthesis and structure peculiarity of quinoxaline derivatives with two benzimidazole fragments
  作者：Vakhid A. Mamedov、Nataliya A. Zhukova、Victor V. Syakaev、Aidar T. Gubaidullin、Tat'yana N. Beschastnova、Dil'bar I. Adgamova、Aida I. Samigullina、Shamil K. Latypov

  DOI：10.1016/j.tet.2012.10.045

  日期：2013.1

  A highly efficient and versatile method for the synthesis of quinoxaline derivatives with two benzimidazole fragments have been developed on the basis of the ring contraction of 3-(benzimidazo-2-yl)quinoxalin-2(1H)-one with 1,2-diaminobenzene and its various types of substituted and condensed derivatives. Owing to the inter- and intramolecular processes, involving self association, proton exchange

  基于3-（苯并咪唑-2-基）喹喔啉-2（1 H）-与1,2-的环收缩，已开发出一种高效且通用的具有两个苯并咪唑片段的喹喔啉衍生物的合成方法。二氨基苯及其各种类型的取代和稠合衍生物。由于分子间和分子内过程，涉及桥联和相邻碳原子的大多数双-苯并咪唑基喹喔啉信号的几种形式之间的自缔合，质子交换，构象和/或互变异构交换，且NMR光谱中的苯并咪唑片段变宽。苯并咪唑片段与分子的喹喔啉核心之间的共轭作用比喹喔啉衍生物（10c）与其噻二唑[ f ]-（17）和吡咯并[ a ]-（19）环化了衍生物，导致整个分子的平面度更大。
• A versatile one-step method for the synthesis of benzimidazoles from quinoxalinones and arylenediamines via a novel rearrangement
  作者：Vakhid A. Mamedov、Dina F. Saifina、Il’dar Kh. Rizvanov、Aidar T. Gubaidullin

  DOI：10.1016/j.tetlet.2008.05.060

  日期：2008.7

  A highly efficient and versatile method for the synthesis of benzimidazoles has been developed on the basis of the novel ring contraction of 3-aroyl- and 3-alkanoylquinoxalin-2-ones with 1,2-arylenediamines.

  在3-芳酰基-和3-烷酰基喹喔啉-2-酮与1，2-芳基二胺的新型环收缩的基础上，已经开发了一种高效且通用的合成苯并咪唑的方法。
• Application of theoretically computed chemical shifts to structure determination of novel heterocyclic compounds
  作者：Alsu Balandina、Dina Saifina、Vakhid Mamedov、Shamil Latypov

  DOI：10.1016/j.molstruc.2006.01.008

  日期：2006.6

  Combined use of 2D NMR correlation methods (H-1-C-13 and H-1-N-15 2D HMBC) and the DFT-GIAO chemical shift calculations allows unequivocal determination of structure for novel quinoxaline. Such interplay of experiment and theory is really reliable and convenient way for structure elucidation of complex heterocycles. (c) 2006 Elsevier B.V. All rights reserved.
• Bodforss, Justus Liebigs Annalen der Chemie, 1957, vol. 609, p. 103,117
  作者：Bodforss

  DOI：——

  日期：——
• 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.