N,N-dimethyl-4-(quinazolin-2-yl)aniline

• 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: N,N-dimethyl-4-(quinazolin-2-yl)aniline
• 英文别名: N,N-dimethyl-4-quinazolin-2-ylaniline
• 化学式: C₁₆H₁₅N₃
• 分子量: 249.315
• InChiKey: BRGOKHPOESNHQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(4-N,N-dimethylaminophenyl)-1,2,3,4-tetrahydroquinazoline 在 activated MnO₂ 作用下， 以 氯仿 为溶剂， 反应 12.0h， 生成 N,N-dimethyl-4-(quinazolin-2-yl)aniline
  参考文献：
  名称：

  基于喹唑啉的CYP1A2抑制剂的设计，合成和酶促表征。

  摘要：

  细胞色素P450同工酶1A2（CYP1A2）是人类中一种主要的异源生物代谢酶。它与致癌物的生物活化有关，包括4-（甲基亚硝胺基）-1-（3-吡啶基）-1-丁酮（NNK），这是一种烟草特有的强效肺致癌物。这项工作描述了潜在的CYP1A2抑制剂的计算设计和计算机筛选，其化学合成和酶促表征，其最终目的是评估其作为癌症化学预防剂的潜力。为实现此目的，使用组合的分类器模型对已知的CYP1A2抑制剂，非抑制剂和底物筛选基于喹唑啉的分子文库，以预测哪些喹唑啉候选物作为抑制剂的可能性更高。通过Glide对接进一步对具有CYP1A2抑制作用的化合物进行了计算评估。合成了对CYP1A2具有选择性和高结合亲和力的候选化合物，并测定了其对CYP1A2的酶促抑制作用，从而发现了新颖且有效的基于喹唑啉的CYP1A2抑制剂。

  DOI：

  10.1016/j.bmcl.2019.126719

文献信息

• Efficient synthesis of quinazolines by the iron-catalyzed acceptorless dehydrogenative coupling of (2-aminophenyl)methanols and benzamides
  作者：Shi-Qi Zhang、Yao Cui、Bin Guo、David J. Young、Ze Xu、Hong-Xi Li

  DOI：10.1016/j.tet.2020.131825

  日期：2021.1

  The acceptorless dehydrogenation coupling (ADC) of (2-aminophenyl)methanols with benzamides was achieved with catalytic FeCl2·4H2O in an efficient synthesis of quinazolines. This simple catalytic system is atom-economical, environmentally benign and suited to a variety of substrates.

  在催化合成高效的喹唑啉中，用催化FeCl 2 ·4H 2 O实现了（2-氨基苯基）甲醇与苯甲酰胺的无受体脱氢偶联（ADC）。这种简单的催化系统是原子经济的，对环境无害的，适用于各种基材。
• A convenient palladium-catalyzed carbonylative synthesis of quinazolines from 2-aminobenzylamine and aryl bromides
  作者：Jianbin Chen、Kishore Natte、Helfried Neumann、Xiao-Feng Wu

  DOI：10.1039/c4ra11303a

  日期：——

  A novel and practical strategy towards quinazoline scaffolds synthesis has been achieved. Through palladium-catalyzed carbonylative coupling of 2-aminobenzylamine with aryl bromides, the desired quinazolines were produced in moderate to good yields for the first time. The reactions followed an aminocarbonylation–condensation–oxidation sequence in a one-pot one-step manner. Preliminary investigation

  已经实现了一种新颖且实用的喹唑啉支架合成策略。通过2-氨基苄基胺与芳基溴化物的钯催化羰基偶合，首次以中等至良好的收率生产了所需的喹唑啉。反应遵循一键式一步反应的氨基羰基化-缩合-氧化顺序。初步研究表明，DMSO在此过程中既充当溶剂又充当氧化剂。
• Synthesis of quinazolines from (2-aminoaryl)methanols and arylmethanamines catalyzed by rhodium complex
  作者：L. Wang、J. Cao、Z. Li

  DOI：10.1134/s1070363217040235

  日期：2017.4

  Efficient synthesis of quinazoline derivatives via rhodium-catalyzed dehydrogenation and ring-closing method was developed with moderate to high yields.

  通过铑催化的脱氢和闭环方法，以中等至高收率开发了一种高效合成喹唑啉衍生物的方法。
• Bioinspired Aerobic Oxidation of Secondary Amines and Nitrogen Heterocycles with a Bifunctional Quinone Catalyst
  作者：Alison E. Wendlandt、Shannon S. Stahl

  DOI：10.1021/ja411692v

  日期：2014.1.8

  Copper amine oxidases are a family of enzymes with quinone cofactors that oxidize primary amines to aldehydes. The native mechanism proceeds via an iminoquinone intermediate that promotes high selectivity for reactions with primary amines, thereby constraining the scope of potential biomimetic synthetic applications. Here we report a novel bioinspired quinone catalyst system consisting of 1,10-phenanthroline-5,6-dione/ZnI2 that bypasses these constraints via an abiological pathway involving a hemiaminal intermediate. Efficient aerobic dehydrogenation of non-native secondary amine substrates, including pharmaceutically relevant nitrogen heterocycles, is demonstrated. The ZnI2 cocatalyst activates the quinone toward amine oxidation and provides a source of iodide, which plays an important redox-mediator role to promote aerobic catalytic turnover. These findings provide a valuable foundation for broader development of aerobic oxidation reactions employing quinone-based catalysts.
• A Novel Ruthenium-Catalyzed Dehydrogenative Synthesis of 2-Arylquinazolines from 2-Aminoaryl Methanols and Benzonitriles
  作者：Mengmeng Chen、Min Zhang、Biao Xiong、Zhenda Tan、Wan Lv、Huanfeng Jiang

  DOI：10.1021/ol503052s

  日期：2014.11.21

  By employing a commercially available Ru-3(CO)(12)/Xantphos/t-BuOK catalyst system, a novel and straightforward ruthenium-catalyzed dehydrogenative synthesis of 2-arylquinazolines has been demonstrated. A series of 2-aminoaryl methanols were efficiently converted in combination with different types of benzonitriles into various desired products in moderate to good yields upon isolation. The synthetic protocol proceeds with the advantages of operational simplicity, high atom efficiency, broad substrate scope, and no need for the use of less environmentally benign halogenated reagents, offering an important basis for accessing 2-arylquinazolines.