2-(allylamino)-N-benzylbenzamide | 1408002-67-4

• 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: 2-(allylamino)-N-benzylbenzamide
• 英文别名: 2-(Allylamino)-N-benzylbenzamide；N-benzyl-2-(prop-2-enylamino)benzamide
• CAS: 1408002-67-4
• 化学式: C₁₇H₁₈N₂O
• mdl: MFCD26406888
• 分子量: 266.343
• InChiKey: RWMILTIZBQAZFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.117
• 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：

  2-(allylamino)-N-benzylbenzamide 在 copper(l) iodide 、 氧气 、 potassium carbonate 、 manganese(IV) oxide 作用下， 以 二甲基亚砜 为溶剂， 反应 8.08h， 以30%的产率得到3-benzyl-3H-quinazolin-4-one
  参考文献：
  名称：

  铜催化 CH 酰胺化反应合成 2,3-二取代喹唑啉酮衍生物

  摘要：

  喹唑啉酮衍生物的合成是由2-碘代苯甲酰胺衍生物与各种苄胺、烯丙胺和肉桂胺衍生物通过一锅铜催化反应合成的。在该反应中，胺组分（苄胺/烯丙胺/肉桂胺）通过 Ullman 偶联与 2-碘苯甲酰胺衍生物进行 N-芳基化，然后在铜催化剂存在下进行分子内 C-H 酰胺化。

  DOI：

  10.1002/ejoc.201501552
• 作为产物：
  描述：

  靛红酸酐 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基乙酰胺 、 二甲基亚砜 为溶剂， 生成 2-(allylamino)-N-benzylbenzamide
  参考文献：
  名称：

  Novel 2-Aminobenzamides as Potential Orally Active Antithrombotic Agents

  摘要：

  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.

  DOI：

  10.1021/ml300217f

文献信息

• 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。
• Synthesis of 2,3-Disubstituted Quinazolinone Derivatives through Copper Catalyzed C-H Amidation Reactions
  作者：Trimurtulu Kotipalli、Veerababurao Kavala、Donala Janreddy、Vijayalakshmi Bandi、Chun-Wei Kuo、Ching-Fa Yao

  DOI：10.1002/ejoc.201501552

  日期：2016.2

  The synthesis of quinazolinone derivatives was achieved from 2-iodobenzamide derivatives and various benzylamines, allylamine, and cinnamylamine derivatives through a one-pot copper-catalyzed reaction. In this reaction, the amine component (benzylamine/allylamine/cinnamylamine) is N-arylated with 2-iodobenzamide derivatives through Ullman coupling, followed by an intramolecular C–H amidation in the

  喹唑啉酮衍生物的合成是由2-碘代苯甲酰胺衍生物与各种苄胺、烯丙胺和肉桂胺衍生物通过一锅铜催化反应合成的。在该反应中，胺组分（苄胺/烯丙胺/肉桂胺）通过 Ullman 偶联与 2-碘苯甲酰胺衍生物进行 N-芳基化，然后在铜催化剂存在下进行分子内 C-H 酰胺化。
• 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.