2-(4-bromophenyl)-6-chloro-2,3-dihydroquinazolin-4(1H)-one | 1375103-46-0

• 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: 2-(4-bromophenyl)-6-chloro-2,3-dihydroquinazolin-4(1H)-one
• 英文别名: 2-(4-bromophenyl)-6-chloro-2,3-dihydroquinazoli-4(1H)-one；2-(4-bromophenyl)-6-choloro-2,3-dihydroquinazolin-4(1H)-one；2-(4-bromophenyl)-6-chloro-2,3-dihydro-1H-quinazolin-4-one
• CAS: 1375103-46-0
• 化学式: C₁₄H₁₀BrClN₂O
• 分子量: 337.603
• InChiKey: FGSATOGAHYKFGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  41.13
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  对溴苯甲醛 、 2-氨基-5-氯苯甲酰胺 在 indium(III) bromide 作用下， 以 乙腈 为溶剂， 反应 0.83h， 以96%的产率得到2-(4-bromophenyl)-6-chloro-2,3-dihydroquinazolin-4(1H)-one
  参考文献：
  名称：

  2,3-二氢喹唑啉-4(1H)-one 衍生物的便捷和可扩展合成及其抗癌活性

  摘要：

  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

  DOI：

  10.1080/00397911.2015.1046555

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
• Probing Carbocatalytic Activity of Carbon Nanodots for the Synthesis of Biologically Active Dihydro/Spiro/Glyco Quinazolinones and Aza-Michael Adducts
  作者：Biju Majumdar、Sonam Mandani、Tamalika Bhattacharya、Daisy Sarma、Tridib K. Sarma

  DOI：10.1021/acs.joc.6b02914

  日期：2017.2.17

  the fluorescent carbon dots as an effective and recyclable carbocatalyst for the generation of carbon–heteroatom bond leading to quinazolinone derivatives and aza-Michael adducts under mild reaction conditions. The results establish this nanoscale form of carbon as an alternative carbocatalyst for important acid catalyzed organic transformations. The mild surface acidity of carbon dots imparted by

  本文中，我们报道了荧光碳点是有效且可回收的碳催化剂，可在温和的反应条件下生成碳-杂原子键，从而导致喹唑啉酮衍生物和氮杂-迈克尔加合物。结果确定了这种碳的纳米级形式，可作为重要的酸催化的有机转化的替代碳催化剂。在当前反应条件下，-COOH官能团赋予的碳点温和的表面酸性可以有效催化合成挑战性的螺/糖基喹唑啉酮的形成。
• 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).
• 5,5’-Indigodisulfonic acid as an efficient catalyst for the synthesis of 2,3-dihydroquinazolinone derivatives
  作者：Cheng-Hang Liu、Qiong Wang、Zenglai Xu、Dongling Li、Yuhong Zheng

  DOI：10.1080/00397911.2022.2098045

  日期：2022.7.18

  Abstract An efficient protocol for the synthesis of 2,3-dihydroquinazolinone derivatives from substituted 2-aminobenzamides and carbonyl analog catalyzed by the natural-based 5,5’-indigodisulfonic acid has been developed with good to excellent yields. Compared to the reaction conditions reported before, the use of eco-friendly and recyclable catalysts and mild reaction conditions are the major advantages

  摘要 已开发出一种有效的方案，用于从取代的 2-氨基苯甲酰胺和由天然基 5,5'-靛蓝二磺酸催化的羰基类似物合成 2,3-二氢喹唑啉酮衍生物，收率良好。与之前报道的反应条件相比，使用环保和可回收的催化剂和温和的反应条件是本方法的主要优点。