N-benzyl-2-(benzylamino)benzamide | 1347035-20-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-benzyl-2-(benzylamino)benzamide
• CAS: 1347035-20-4
• 化学式: C₂₁H₂₀N₂O
• mdl: MFCD25369875
• 分子量: 316.403
• InChiKey: UNZSSDLGKOLARO-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：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.095
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-benzyl-2-(benzylamino)benzamide 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 3-benzyl-2-phenyl-3,4-dihydroquinazolin-4-one
  参考文献：
  名称：

  One pot synthesis of some new N-allyl and N-benzyl quinazolinones and their anti-inflammatory activity

  摘要：

  DOI：

  10.1016/j.jics.2021.100033
• 作为产物：
  描述：

  N-苄基-2-溴苯甲酰胺 、 苄胺 在 potassium phosphate 、 copper(l) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以84%的产率得到N-benzyl-2-(benzylamino)benzamide
  参考文献：
  名称：

  The N-Aryl Aminocarbonyl ortho-Substituent Effect in Cu-Catalyzed Aryl Amination and Its Application in the Synthesis of 5-Substituted 11-Oxo-dibenzodiazepines

  摘要：

  Double amination of ortho-substituted aryl bromides proceeded under mild conditions to afford 5-substituted 11-oxo-dibenzodiazepines, which revealed that there is a strong ortho-substituent effect caused by N-aryl aminocarbonyl groups during copper-catalyzed aryl amination.

  DOI：

  10.1021/ol202721h

文献信息

• Water as a hydrogen source in palladium-catalyzed reduction and reductive amination of nitroarenes mediated by diboronic acid
  作者：Yanmei Zhou、Haifeng Zhou、Sensheng Liu、Danwei Pi、Guanshuo Shen

  DOI：10.1016/j.tet.2017.05.056

  日期：2017.7

  An unprecedented palladium-catalyzed chemoselective reduction and reductive amination of nitroarenes with water as a hydrogen source mediated by diboronic acid have been discovered. A series of aryl amines containing various reducible functional groups were obtained in good to excellent yields.

  已经发现了前所未有的钯催化的以水为氢由二硼酸介导的硝基芳烃的化学选择性还原和还原胺化反应。以良好至优异的产率获得了一系列包含各种可还原官能团的芳基胺。
• Iodine-Promoted Oxidative Cyclization of Acylated and Alkylated Derivatives from Epoxides toward the Synthesis of Aza Heterocycles
  作者：Alageswaran Jayaram、Karthick Govindan、Vijaya Raghavan Kannan、Vijay Thavasianandam Seenivasan、Nian-Qi Chen、Wei-Yu Lin

  DOI：10.1021/acs.joc.2c02802

  日期：2023.2.3

  A new method for directly synthesizing acylated and alkylated quinazoline derivatives by the epoxide ring-opening reaction in the presence of I2/DMSO with 2-aminobenzamide is described herein. The developed mild protocol is efficient and displays a wide variety of functional group tolerance and substrate-controlled high selectivity, and the application of a continuous flow technique allows for faster

  本文介绍了一种在I 2 /DMSO存在下与2-氨基苯甲酰胺通过环氧化物开环反应直接合成酰化和烷基化喹唑啉衍生物的新方法。开发的温和协议是高效的，并显示出广泛的官能团耐受性和底物控制的高选择性，并且连续流动技术的应用允许更快的反应时间和更高的产量。此外，该方法的稳健性适用于克级合成。
• Novel 2-Aminobenzamides as Potential Orally Active Antithrombotic Agents
  作者：Amit Verma、Rajani Giridhar、Ashish Kanhed、Anshuman Sinha、Pratik Modh、Mange R. Yadav

  DOI：10.1021/ml300217f

  日期：2013.1.10

  In an effort to develop potent antithrombotic agents, a series of novel 2-aminobenzamide derivatives were synthesized and screened for their in vivo antithrombotic activity. Among the 23 compounds tested, compound (8g) showed the most promising antithrombotic activity, which was comparable with clinically used aspirin or warfarin, but at variance with these standard drugs, 8g did not exhibit the increased bleeding time, suggesting its potential as a novel antithrombotic agent.
• The <i>N</i>-Aryl Aminocarbonyl <i>ortho</i>-Substituent Effect in Cu-Catalyzed Aryl Amination and Its Application in the Synthesis of 5-Substituted 11-Oxo-dibenzodiazepines
  作者：Xiaoqiong Diao、Lanting Xu、Wei Zhu、Yongwen Jiang、Haoyang Wang、Yinlong Guo、Dawei Ma

  DOI：10.1021/ol202721h

  日期：2011.12.16

  Double amination of ortho-substituted aryl bromides proceeded under mild conditions to afford 5-substituted 11-oxo-dibenzodiazepines, which revealed that there is a strong ortho-substituent effect caused by N-aryl aminocarbonyl groups during copper-catalyzed aryl amination.
• One pot synthesis of some new N-allyl and N-benzyl quinazolinones and their anti-inflammatory activity
  作者：Sudharshan Reddy Sudula、Ranjith Jala、Kavitha Siddoju、Jagadeesh Kumar Ega

  DOI：10.1016/j.jics.2021.100033

  日期：2021.3