2-(2-chlorophenyl)-3-phenylquinazolin-4(3H)-one | 887628-91-3

• 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-(2-chlorophenyl)-3-phenylquinazolin-4(3H)-one
• 英文别名: 2-(2-Chlorophenyl)-3-phenylquinazolin-4-one
• CAS: 887628-91-3
• 化学式: C₂₀H₁₃ClN₂O
• 分子量: 332.789
• InChiKey: AKPJDDZYOWZJII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-硝基苯甲酰氯 在 1,1'-双(二苯基膦)二茂铁 、 三乙胺 作用下， 以 二氯甲烷 、 氯苯 为溶剂， 反应 26.0h， 生成 2-(2-chlorophenyl)-3-phenylquinazolin-4(3H)-one
  参考文献：
  名称：

  Iron-Catalyzed One-Pot 2,3-Diarylquinazolinone Formation from 2-Nitrobenzamides and Alcohols

  摘要：

  A novel approach for the synthesis of 2,3-diarylquinazolinones using iron as catalyst is described. Various 2-nitro-N-arylbenzamides reacted with benzylic alcohols to selectively give the corresponding products in the absence of external oxidant or reductant.

  DOI：

  10.1021/ol402350x

文献信息

• One-Pot Synthesis of Quinazolin-4(3<i>H</i>)-ones through Anodic Oxidation and the Related Mechanistic Studies
  作者：Liu Cao、Hengrui Huo、Haipeng Zeng、Yu Yu、Dengfu Lu、Yuefa Gong

  DOI：10.1002/adsc.201800927

  日期：2018.12.21

  A metal‐free and oxidant‐free method for the one‐pot preparation of quinazolin‐4(3H)‐ones enabled by electrochemical oxidation is described. Together with 2‐aminobenzamides, a variety of aldehydes were successfully applied to an acid‐catalyzed annulation and direct anodic oxidation cascade, affording structurally diverse quinazoline‐4(3H)‐ones in good to excellent yields. Additionally, certain alcohols

  描述了一种通过电化学氧化一锅法制备喹唑啉-4（3H）-酮的无金属，无氧化剂的方法。与2-氨基苯甲酰胺一起，已将多种醛成功应用于酸催化的环化反应和直接的阳极氧化级联反应，从而提供了结构多样的喹唑啉-4（3H）-酮，产率高至优异。此外，在电解介质（TEMPO）的辅助下，可以直接使用某些醇类代替相应的醛类来获得相同的最终产品。仔细检查了反应机理，结果强烈表明直接和间接氧化经历不同的途径。作为有效和环保的途径，可以使用各种喹唑啉-4（3H）-ones，该方法的合成效用已通过克级操作证明，并制备了生物活性麦角唑啉酮和截短的厄洛替尼。
• Synthesis of quinazolinones from anthranilamides and aldehydes via metal-free aerobic oxidation in DMSO
  作者：Na Yeun Kim、Cheol-Hong Cheon

  DOI：10.1016/j.tetlet.2014.02.065

  日期：2014.4

  A highly environmentally benign protocol for the synthesis of quinazolinones from anthranilamides and aldehydes via aerobic oxidation was developed in wet DMSO. This protocol is operationally simple, exhibits broad substrate scope, and does not need toxic metal catalysts and bases. In addition, the utility of this transformation was further demonstrated by converting the resulting quinazolinones into

  在湿式DMSO中开发了一种高度环境友好的方案，该方案通过需氧氧化由邻氨基苯甲酰胺和醛合成喹唑啉酮。该方案操作简单，具有广泛的底物范围，并且不需要有毒的金属催化剂和碱。另外，通过将所得的喹唑啉酮类在同一罐中无需分离即可转化为其他有用的产物，进一步证明了这种转化的效用。
• Efficient and Practical One-Pot Route to Synthesise Quinazolin4(3H)-Ones Using Trifluoromethanesulfonic Anhydride and 2-Chloropyridine
  作者：Mohsen Dadgar、Nasim Milani Kalkhorani

  DOI：10.3184/174751915x14229898818046

  日期：2015.2

  An effective, novel and rapid one-pot three-component route to quinazolin-4(3H)-ones from commercially available starting materials is described. Isatoic anhydride reacts with acyl chlorides and different amines using a combination of trifluoromethanesulfonic anhydride (Tf₂O) and 2-chloropyridine (2-ClPy) to produce the corresponding quinazolinone derivatives in good to excellent yields.

  本研究描述了从市售起始原料制备喹唑啉-4(3H)-酮的有效、新颖和快速的单锅三组分路线。利用三氟甲磺酸酐（Tf2O）和 2-氯吡啶（2-ClPy）的组合，异酸酐与酰基氯和不同的胺发生反应，以良好到极佳的收率生成相应的喹唑啉酮衍生物。
• Biomass derived Cu₂O nanoparticles for N-atom insertion reactions: a base-free synthesis of quinazolinones with a green approach
  作者：Thrilokraj R.、Jan Grzegorz Małecki、Srinivasa Budagumpi、Umesh A. Kshirsagar、Ramesh B. Dateer

  DOI：10.1039/d4gc00569d

  日期：2024.4.22

  This work describes the use of an eco-friendly biogenic approach for the synthesis of Cu₂O NPs utilizing Cucumis melo peel extract for the first time and employed for the one-pot multicomponent synthesis of quinazolinones in a green solvent.
• Iron-Catalyzed One-Pot 2,3-Diarylquinazolinone Formation from 2-Nitrobenzamides and Alcohols
  作者：Huamin Wang、Xiangxiang Cao、Fuhong Xiao、Saiwen Liu、Guo-Jun Deng

  DOI：10.1021/ol402350x

  日期：2013.9.20

  A novel approach for the synthesis of 2,3-diarylquinazolinones using iron as catalyst is described. Various 2-nitro-N-arylbenzamides reacted with benzylic alcohols to selectively give the corresponding products in the absence of external oxidant or reductant.