6-chloro-2-(4-methoxyphenyl)-2,3-dihydroquinazolin-4(1H)-one | 1024593-51-8

• 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-(4-methoxyphenyl)-2,3-dihydroquinazolin-4(1H)-one
• 英文别名: 6-chloro-2-(4-methoxyphenyl)-2,3-dihydro-1H-quinazolin-4-one
• CAS: 1024593-51-8
• 化学式: C₁₅H₁₃ClN₂O₂
• 分子量: 288.733
• InChiKey: SFIVORDZQWNDSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  50.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-氯靛红酸酐 、 4-甲氧基苯甲醛 在 gallium(III) triflate ammonium acetate 作用下， 以 乙醇 为溶剂， 反应 0.67h， 以83%的产率得到6-chloro-2-(4-methoxyphenyl)-2,3-dihydroquinazolin-4(1H)-one
  参考文献：
  名称：

  三氟甲磺酸镓（III）催化一锅选择性合成2,3-二氢喹唑啉-4（1 H）-one和喹唑啉-4（3 H）-one

  摘要：

  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。

  DOI：

  10.1016/j.tetlet.2008.03.127

文献信息

• 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
• Electrostatically Enhanced Sulfuric Acid: A Strong Brønsted Acidic Catalyst for Multi-Component Reactions
  作者：Mohadese Yaghoobi Anzabi、Hossein Yazdani、Ayoob Bazgir

  DOI：10.1007/s10562-019-02776-w

  日期：2019.7

  A new electrostatically enhanced sulfuric acid as a strong Brønsted acidic catalyst has been developed for multi-component reactions. A positively charged center in the catalyst electrostatically activates it for acid-catalyzed multi-component reactions and afforded desired products in short reaction time and near room temperature in EtOH as a green solvent.Graphical Abstract

  一种新的静电增强硫酸作为强 Brønsted 酸性催化剂已被开发用于多组分反应。催化剂中带正电荷的中心通过静电激活它进行酸催化的多组分反应，并在作为绿色溶剂的 EtOH 中在较短的反应时间内和接近室温的时间内提供所需的产物。
• 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。
• Thiamine hydrochloride (VB1) as an efficient promoter for the one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones
  作者：Yijia Chen、Weiguang Shan、Min Lei、Lihong Hu

  DOI：10.1016/j.tetlet.2012.08.090

  日期：2012.10

  A facile, efficient, and environmentally friendly procedure for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones from isatoic anhydride, aldehyde, and ammonium acetate in the presence of thiamine hydrochloride (VB1) in EtOH is described. The protocol proves to be efficient and environmentally benign in terms of high yields, ease of recovery, and reusability of catalyst. (C) 2012 Elsevier Ltd. All rights reserved.