5,12-diacetyl-7,10-dichloro-5,12-dihydroquinoxalino[2,3-b]quinoxaline | 1140899-32-6

• 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: 5,12-diacetyl-7,10-dichloro-5,12-dihydroquinoxalino[2,3-b]quinoxaline
• 英文别名: 1-(6-Acetyl-1,4-dichloroquinoxalino[2,3-b]quinoxalin-11-yl)ethanone；1-(6-acetyl-1,4-dichloroquinoxalino[2,3-b]quinoxalin-11-yl)ethanone
• CAS: 1140899-32-6
• 化学式: C₁₈H₁₂Cl₂N₄O₂
• 分子量: 387.225
• InChiKey: QHIRHQWLYXKUMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  66.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  7,10-dichloro-5,12-dihydroquinoxalino[2,3-b]quinoxaline 、 乙酸酐 反应 16.0h， 以95%的产率得到5,12-diacetyl-7,10-dichloro-5,12-dihydroquinoxalino[2,3-b]quinoxaline
  参考文献：
  名称：

  A new and efficient synthetic approach to dichlorofluoflavines. Study of the stability of isomeric fluoflavines by HF and B3LYP procedures

  摘要：

  The first method for the synthesis of 7,10-dichloro-5,12-dihydroquinoxalino[2,3-b]quinoxalines is reported. Treatment of 3,3,6,6-tetrachloro-1,2-cyclohexanedione with diaminomaleonitrile leads to 5,8-dichloro-2,3-dicyanoquinoxaline in near quantitative yields. This compound has been found to be an excellent synthetic equivalent of unavailable 2,3,5,8-tetrachloroquinoxaline. It reacts with o-phenyl-enediamines Providing the corresponding dichlorofluoflavines in fair to high yields. These compounds have been identified by NMR spectroscopy and X-ray crystallography. Molecular structures, chemical hardness, Delta G(298)(not equal)-values, and relative stabilities of all possible isomeric products have been calculated by HE and B3LYP density functional theory methods. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.01.059

文献信息

• A new and efficient synthetic approach to dichlorofluoflavines. Study of the stability of isomeric fluoflavines by HF and B3LYP procedures
  作者：Antonio Guirado、José I. López-Sánchez、Alfredo Cerezo、Delia Bautista、Jesús Gálvez

  DOI：10.1016/j.tet.2009.01.059

  日期：2009.3

  The first method for the synthesis of 7,10-dichloro-5,12-dihydroquinoxalino[2,3-b]quinoxalines is reported. Treatment of 3,3,6,6-tetrachloro-1,2-cyclohexanedione with diaminomaleonitrile leads to 5,8-dichloro-2,3-dicyanoquinoxaline in near quantitative yields. This compound has been found to be an excellent synthetic equivalent of unavailable 2,3,5,8-tetrachloroquinoxaline. It reacts with o-phenyl-enediamines Providing the corresponding dichlorofluoflavines in fair to high yields. These compounds have been identified by NMR spectroscopy and X-ray crystallography. Molecular structures, chemical hardness, Delta G(298)(not equal)-values, and relative stabilities of all possible isomeric products have been calculated by HE and B3LYP density functional theory methods. (C) 2009 Elsevier Ltd. All rights reserved.