3-butanoyl-1H-1,2-dihydroquinoxalin-2-one | 1048656-75-2

• 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-butanoyl-1H-1,2-dihydroquinoxalin-2-one
• 英文别名: 3-Butanoyl-1,2-dihydro-2-oxoquinoxaline；3-butanoyl-1H-quinoxalin-2-one
• CAS: 1048656-75-2
• 化学式: C₁₂H₁₂N₂O₂
• 分子量: 216.239
• InChiKey: LBDXIZHGYNZZEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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-butanoyl-1H-1,2-dihydroquinoxalin-2-one 在 ammonium acetate 作用下， 以 二甲基亚砜 为溶剂， 反应 6.0h， 以15%的产率得到2,5-bis(2-oxo-1,2-dihydroquinoxalin-3-yl)-3,4-diethylpyrrole
  参考文献：
  名称：

  Reaction of 3-Alkanoylquinoxalin-2-Ones with Ammonium Acetate in DMSO – A New Method for the Synthesis of Pyrroles

  摘要：

  The interaction of 3-alkanoylquinoxalin-2-ones with NH4OAc in DMSO at 105-120A degrees D produced pyrrole derivatives according to a novel [D-2+N+D-2] scheme, while the -(CO)-CH2- fragment of the substituent at position 3 of the quinoxalinones served as the source of two-carbon fragments D(2)-D(3) and D(4)-D(5), and the nitrogen source was NH4OAc.

  DOI：

  10.1007/s10593-014-1461-z
• 作为产物：
  描述：

  3-butylquinoxalin-2(1H)-one 在 chromium(VI) oxide 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 4.0h， 以41%的产率得到3-butanoyl-1H-1,2-dihydroquinoxalin-2-one
  参考文献：
  名称：

  Reaction of 3-Alkanoylquinoxalin-2-Ones with Ammonium Acetate in DMSO – A New Method for the Synthesis of Pyrroles

  摘要：

  The interaction of 3-alkanoylquinoxalin-2-ones with NH4OAc in DMSO at 105-120A degrees D produced pyrrole derivatives according to a novel [D-2+N+D-2] scheme, while the -(CO)-CH2- fragment of the substituent at position 3 of the quinoxalinones served as the source of two-carbon fragments D(2)-D(3) and D(4)-D(5), and the nitrogen source was NH4OAc.

  DOI：

  10.1007/s10593-014-1461-z

文献信息

• 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。
• Quinoxaline-benzimidazole rearrangements in the reactions of 3-alkanoylquinoxalin-2-ones with 1,2-phenylenediamines
  作者：A. A. Kalinin、O. G. Isaikina、V. A. Mamedov

  DOI：10.1007/s10593-007-0198-3

  日期：2007.10
• Reaction of 3-Alkanoylquinoxalin-2-Ones with Ammonium Acetate in DMSO – A New Method for the Synthesis of Pyrroles
  作者：A. A. Kalinin、V. A. Mamedov

  DOI：10.1007/s10593-014-1461-z

  日期：2014.5

  The interaction of 3-alkanoylquinoxalin-2-ones with NH4OAc in DMSO at 105-120A degrees D produced pyrrole derivatives according to a novel [D-2+N+D-2] scheme, while the -(CO)-CH2- fragment of the substituent at position 3 of the quinoxalinones served as the source of two-carbon fragments D(2)-D(3) and D(4)-D(5), and the nitrogen source was NH4OAc.