4-(2,4-dichlorophenyl)-1,2,3,4,5,6,7,8-octahydro-2,5-oxo-quinoxalin

• 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: 4-(2,4-dichlorophenyl)-1,2,3,4,5,6,7,8-octahydro-2,5-oxo-quinoxalin
• 英文别名: 4-(2,4-Dichlorophenyl)-1,3,4,6,7,8-hexahydroquinazoline-2,5-dione
• 化学式: C₁₄H₁₂Cl₂N₂O₂
• 分子量: 311.167
• InChiKey: XNKPCXNOMIZOLK-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：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,3-环己二酮 、 2,4-二氯苯甲醛 、 尿素 在 potassium hydrogensulfate 作用下， 以 乙二醇 为溶剂， 以95%的产率得到4-(2,4-dichlorophenyl)-1,2,3,4,5,6,7,8-octahydro-2,5-oxo-quinoxalin
  参考文献：
  名称：

  一种新的Biginelli反应程序，以硫酸氢钾为促进剂，可有效合成3,4-二氢嘧啶-2（1 H）-one

  摘要：

  已经发现简单且改进的条件可以进行Biginelli反应，以合成3,4-二氢嘧啶-2（1 H）-one衍生物。使用硫酸氢钾作为促进剂在乙二醇溶液中进行该合成。与经典的Biginelli反应条件相比，该新方法的优点是收率高（85–95％），反应时间短（0.5–2 h）。

  DOI：

  10.1002/jhet.5570410216

文献信息

• A New Biginelli Reaction Procedure Using Potassium Hydrogen Sulfate as the Promoter for an Efficient Synthesis of 3,4-Dihydropyrimidin-2(1<i>H</i>)-one
  作者：Shujiang Tu、Fang Fang、Songlei Zhu、Tuanjie Li、Xiaojing Zhang、Qiya Zhuang

  DOI：10.1055/s-2004-815419

  日期：——

  conditions have been found to carry out the Biginelli reaction for the synthesis of 3,4-dihydropyrimidin-2(1H)-one derivatives. This synthesis was performed using potassium hydrogen sulfate as the promoter in glycol solution. Compared with the classical Biginelli reaction conditions, this new method has the advantage of excellent yields (85-99%) and short reaction time (0.5-2 h).

  已经发现简单和改进的条件可以进行 Biginelli 反应以合成 3,4-二氢嘧啶-2(1H)-one 衍生物。该合成是在乙二醇溶液中使用硫酸氢钾作为促进剂进行的。与经典的 Biginelli 反应条件相比，这种新方法具有收率高（85-99%）和反应时间短（0.5-2 h）的优点。
• A new biginelli reaction procedure using potassium hydrogen sulfate as the promoter for an efficient synthesis of 3,4-dihydropyrimidin-2(1<i>H</i>)-one
  作者：Shujiang Tu、Fang Fang、Songlei Zhu、Tuanjie Li、Xiaojing Zhang、Qiya Zhuang

  DOI：10.1002/jhet.5570410216

  日期：2004.3

  conditions have been found to carry out the Biginelli reaction for the synthesis of 3,4-dihydropyrimidin-2(1H)-one derivatives. This synthesis was performed using potassium hydrogen sulfate as the promoter in ethylene glycol solution. Compared with the classical Biginelli reaction conditions, this new method has the advantage of excellent yields (85–95%) and short reaction time (0.5–2 h).

  已经发现简单且改进的条件可以进行Biginelli反应，以合成3,4-二氢嘧啶-2（1 H）-one衍生物。使用硫酸氢钾作为促进剂在乙二醇溶液中进行该合成。与经典的Biginelli反应条件相比，该新方法的优点是收率高（85–95％），反应时间短（0.5–2 h）。
• A Practical Approach Towards Synthesis of Octahydroquinazolinone Derivatives in Water
  作者：Hai-Xia Lin、Xiao-Zhen Xie、Xiao-Hong Wang、Bin He

  DOI：10.2174/157017809789869555

  日期：2009.10.1

  A simple, efficient and green procedure has been developed for the synthesis of octahydroquinazolinone derivatives by Biginelli-type three-component cyclocondensation reactions of cyclic β-diketones, aldehydes and (thio)urea with p-TsOH catalysis in water.

  在 p-TsOH 催化下，通过环 β-二酮、醛和（硫代）脲在水中的 Biginelli 型三组分环缩合反应，开发了一种简单、高效和绿色的八氢喹唑啉酮衍生物合成工艺。
• Electron Impact Induced Fragmentation of 4-Aryl-4,6,7,8-tetrahydro-1H,3H-quinazoline-2,5-diones
  作者：Wolfgang Wiegrebe、Klaus K. Mayer、Stefan Dove、Herwig Pongratz、Mevlüt Ertan

  DOI：10.3987/com-98-8133

  日期：——
• Ionic liquid: an efficient and recyclable medium for the synthesis of octahydroquinazolinone and biscoumarin derivatives
  作者：Jitender M. Khurana、Sanjay Kumar

  DOI：10.1007/s00706-010-0306-4

  日期：2010.5

  A facile and environmentally benign procedure for the synthesis of octahydroquinazolinone and biscoumarin derivatives in ionic liquids is reported. Octahydroquinazolinones were synthesized in the presence of trimethylsilyl chloride (TMSCl) while the synthesis of biscoumarins required no additive. The ability to reuse the ionic liquid, the high yields, and ease of purification are the important features of this process.