6-chloro-2-(p-tolyl)-2,3-dihydroquinazolin-4(1H)-one | 1021953-82-1

• 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: 6-chloro-2-(p-tolyl)-2,3-dihydroquinazolin-4(1H)-one
• 英文别名: 6-Chloro-2,3-dihydro-2-(4-methylphenyl)-4(1H)-quinazolinone；6-chloro-2-(4-methylphenyl)-2,3-dihydro-1H-quinazolin-4-one
• CAS: 1021953-82-1
• 化学式: C₁₅H₁₃ClN₂O
• 分子量: 272.734
• InChiKey: YKOHCBBLSGCLSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  对甲基苯甲醛 、 2-氨基-5-氯苯甲酰胺 在 phosphotungstic acid 作用下， 以 水 为溶剂， 反应 0.13h， 以94%的产率得到6-chloro-2-(p-tolyl)-2,3-dihydroquinazolin-4(1H)-one
  参考文献：
  名称：

  水中杂多酸催化高效合成2,3-二氢喹唑啉-4（1H）-酮

  摘要：

  摘要杂多酸有效地催化了邻氨基苯甲酰胺与醛在水中在环境温度下的环缩合反应，并以良好或优异的收率得到了相应的2,3-二氢-4（1 H）-喹唑啉酮类化合物。该方法使用少量催化剂和简单的后处理程序即可提供温和的反应条件和干净的反应曲线。

  DOI：

  10.1016/j.cclet.2010.03.022

文献信息

• Gallium(III) triflate-catalyzed one-pot selective synthesis of 2,3-dihydroquinazolin-4(1H)-ones and quinazolin-4(3H)-ones
  作者：Jiuxi Chen、Dengze Wu、Fei He、Miaochang Liu、Huayue Wu、Jinchang Ding、Weike Su

  DOI：10.1016/j.tetlet.2008.03.127

  日期：2008.6

  A series of 2,3-dihydroquinazolin-4(1H)-ones and quinazolin-4(3H)-ones have been synthesized in good to excellent yields and high selectivity by one-pot reaction using isatoic anhydride, ammonium acetate (or amines), and aldehydes in ethanol or in DMSO under mild conditions, respectively. The reaction was efficiently promoted by 1 mol % Ga(OTf)3 and the catalyst could be recovered easily after the

  一系列的2,3-二氢喹唑啉-4（1 H）-和喹唑啉-4（3 H）-已通过使用等位酸酐，乙酸铵（或胺和乙醛分别在温和条件下的乙醇或DMSO中。通过1mol％的Ga（OTf）3有效地促进了反应，并且反应后催化剂可以容易地回收并重复使用而没有明显的反应性损失。
• Convenient and Scalable Synthesis of 2,3-Dihydroquinazolin-4(1<i>H</i>)-one Derivatives and Their Anticancer Activities
  作者：Lingayya Rajaka、Nageshwar Rao Penumati、K. Nagaiah、Y. Poornachandra、C. Ganesh Kumar

  DOI：10.1080/00397911.2015.1046555

  日期：2015.8.18

  InBr3-catalyzed approach to synthesize 2,3-dihydroquinazolin-4(1H)-one derivatives (3a–3aa) has been developed. Notably, all the products were isolated by recrystallization and the reaction is accessible on a gram scale. Moreover, the reactions only require 10–60 min. All the synthesized compounds were evaluated for their in vitro anticancer activity against four human cancer cell lines. GRAPHICAL ABSTRACT

  摘要 已开发出一种高效、温和的 InBr3 催化方法来合成 2,3-二氢喹唑啉-4(1H)-one 衍生物 (3a-3aa)。值得注意的是，所有产物都通过重结晶分离，反应可以达到克级规模。此外，反应只需要 10-60 分钟。评估了所有合成的化合物对四种人类癌细胞系的体外抗癌活性。图形概要
• Tandem synthesis of 2,3-dihydroquinazolin-4(1H)-ones on grinding under solvent-free conditions
  作者：Quan-Sheng Ding、Ji-Lei Zhang、Jiu-Xi Chen、Miao-Chang Liu、Jin-Chang Ding、Hua-Yue Wu

  DOI：10.1002/jhet.759

  日期：2012.3

  AbstractCitric acid promoted synthesis of a mini‐library 2,3‐dihydroquinazolin‐4(1H)‐ones with good to excellent yields is achieved by tandem reaction of anthranilamides (or anthranilhydrazides) with aldehydes on grinding at room temperature under solvent‐free conditions. This method has notable advantages in terms of simple workup, short reaction time, cost‐effective, and environmentally benign. J. Heterocyclic Chem., (2012).
• Highly efficient synthesis of 2,3-dihydroquinazolin-4(1H)-ones catalyzed by heteropoly acids in water
  作者：YingXiao Zong、Yan Zhao、WenCai Luo、Xing Hai Yu、Jun Ke Wang、Yi Pan

  DOI：10.1016/j.cclet.2010.03.022

  日期：2010.7

  Abstract Heteropoly acids efficiently catalyzed the cyclocondensation reaction of anthranilamide with aldehydes in water at ambient temperature and afforded the corresponding 2,3-dihydro-4(1 H )-quinazolinones compounds in good to excellent yields. This method provides mild reaction conditions and clean reaction profiles, using a small quantity of catalyst and a simple workup procedure.

  摘要杂多酸有效地催化了邻氨基苯甲酰胺与醛在水中在环境温度下的环缩合反应，并以良好或优异的收率得到了相应的2,3-二氢-4（1 H）-喹唑啉酮类化合物。该方法使用少量催化剂和简单的后处理程序即可提供温和的反应条件和干净的反应曲线。