4-(4-chlorophenyl)-3,4,7,8-tetrahydroquinazoline-2,5(1H,6H)-dione

• 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-(4-chlorophenyl)-3,4,7,8-tetrahydroquinazoline-2,5(1H,6H)-dione
• 英文别名: 4-(4-chlorophenyl)-1,2,3,4,5,6,7,8-octahydro-2,5-oxo-quinoxalin；4-(4-Chlorophenyl)-1,3,4,6,7,8-hexahydroquinazoline-2,5-dione
• 化学式: C₁₄H₁₃ClN₂O₂
• 分子量: 276.722
• InChiKey: JUHFTIAEWCQGJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 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：

  4-氯苯甲醛 、 1,3-环己二酮 、 尿素 在 1,4'-(butane-1,4-diyl)-bis-(3-methylimidazolium) di[tetrachloroferrate(III)] 作用下， 以 neat (no solvent) 为溶剂， 反应 1.0h， 以84%的产率得到4-(4-chlorophenyl)-3,4,7,8-tetrahydroquinazoline-2,5(1H,6H)-dione
  参考文献：
  名称：

  [C4（mim）2]（FeCl4）2在无溶剂条件下催化一锅合成八氢喹唑啉酮衍生物

  摘要：

  在这项研究中，描述了一种实用的绿色化学程序，用于在无溶剂条件下通过磁性室温指示液催化醛，1,3-环己二酮/二甲酮与脲或硫脲的缩合反应合成八氢喹唑啉酮和硫酮衍生物。通过紫外光谱，振动样品磁力计和热重分析研究了该催化剂。由于多种优点，例如环境友好，易于实验的过程，良好的收率和可重复使用的催化剂，因此该方法受到关注。

  DOI：

  10.1002/jccs.201300358

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。
• 1-Methylimidazolium hydrogen sulfate/chlorotrimethylsilane: An effective catalytic system for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones and hydroquinazoline-2,5-diones
  作者：Hassan Kefayati、Fatereh Asghari、Raheleh Khanjanian

  DOI：10.1016/j.molliq.2012.01.019

  日期：2012.8

  Brønsted acidic ionic liquid, 1-methylimidazolium hydrogen sulfate, in the presence of catalytic amount of chlorotrimethylsilane has been used as an efficient and reusable catalyst for the one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones and hydroquinazoline-2,5-diones under thermal and solvent-free conditions. High yields of the products were obtained in a few minutes by using this new catalysis

  在催化量的氯三甲基硅烷存在下，布朗斯台德酸性离子液体1-甲基咪唑硫酸氢盐已被用作一种有效且可重复使用的催化剂，用于一锅合成3,4-二氢嘧啶-2（1 H）-一和氢喹唑啉-2,5-二酮在无溶剂和热的条件下。通过使用这种新的催化系统，在几分钟内即可获得高收率的产品。
• 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。
• Solvent-free Synthesis of Novel and Known Octahydroquinazolinones/thiones by the Use of ZrOCl₂.8H₂O as a Highly Efficient and Reusable Catalyst
  作者：Sajad Karami、Bahador Karami、Saeed Khodabakhshi

  DOI：10.1002/jccs.201200145

  日期：2013.1

  A solvent‐free reaction between urea/thiourea, dimedone and aromatic aldehydes in the presence of catalytic amounts of zirconium (IV) oxychloride octahydrate (ZrOCl2.8H2O) as a powerfull Lewis acid leads to octahydroquinazolinone/thione derivatives in good yields. This method has advantages such as avoidance of the organic solvents, production of pure products without any by‐product, short reaction

  尿素/硫脲，二甲酮与芳族醛之间的无溶剂反应在催化量的八氯化氧（IV）八水合氯化锆（ZrOCl 2 .8H 2 O）作为强力路易斯酸存在下，可以以高收率得到八氢喹唑啉酮/硫酮衍生物。该方法具有避免有机溶剂，生产无副产物的纯净产品，反应时间短和操作简单等优点。