N,N-dibenzylaniline | 1253059-22-1

• 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,N-dibenzylaniline
• 英文别名: N,N-bis(2-chlorobenzyl)benzenamine；N,N-bis[(2-chlorophenyl)methyl]aniline
• CAS: 1253059-22-1
• 化学式: C₂₀H₁₇Cl₂N
• 分子量: 342.268
• InChiKey: UZNICKPBHGBVOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N-dibenzylaniline 在 氧气 作用下， 以 丙酮 为溶剂， 反应 35.0h， 以75%的产率得到2-氯-N-苯基苯甲酰胺
  参考文献：
  名称：

  使用可见光诱导的光氧化还原催化的 N,N-二苄基苯胺的非水氧化 C–N 裂解区域选择性合成 2°酰胺

  摘要：

  据报道，可见光驱动的光氧化还原催化的N , N -二苄基苯胺的非水氧化 C-N 裂解为 2° 酰胺。此外，我们已将此协议应用于 2-(二苄基氨基) 苯甲酰胺以提供具有 (NH 4 ) 2 S 2 O 8作为添加剂的喹唑啉酮。机理研究表明，该反应可能通过 C-N 键断裂，然后加入超氧离子形成酰胺，原位生成 α-氨基自由基为亚胺。

  DOI：

  10.1021/acs.joc.1c01792
• 作为产物：
  描述：

  邻氯苄醇 、 硝基苯 在 RuH₂(CO)(PPh₃)₃ 、 1,3-双(2,4,6-三甲基苯基)氯化咪唑 作用下， 反应 16.0h， 以40%的产率得到N,N-dibenzylaniline
  参考文献：
  名称：

  Ruthenium-Catalyzed Tertiary Amine Formation from Nitroarenes and Alcohols

  摘要：

  A highly selective ruthenium-catalyzed C-N bond formation was developed by using the hydrogen-borrowing strategy. Various tertiary amines were obtained efficiently from nitroarenes and primary alcohols. The reaction tolerates a wide range of functionalities. A tentative mechanism was proposed for this direct amination reaction of alcohols with nitroarenes.

  DOI：

  10.1021/ol1020527

文献信息

• An expeditious N,N-dibenzylation of anilines under ultrasonic irradiation conditions using low loading Cu(II)-clay heterogeneous catalyst
  作者：Bashir Ahmad Dar、Varsha Shrivastava、Amrita Bowmik、Mohammad Arif Wagay、Baldev Singh

  DOI：10.1016/j.tetlet.2014.11.044

  日期：2015.1

  A simple one-pot procedure for the direct N,N-dibenzylation of anilines using a catalytic amount of Cu modified montmorillonite-KSF is described. Cu modified montmorillonite-KSF has been proven to be a simple, efficient, mild, convenient, and effective catalyst for the selective benzylation of anilines with benzyl bromide. Cu loading plays a significant role in product yield and solvents were found to control the selectivity. The catalyst is easy to prepare, heterogeneous, stable, and easy to recover. (C) 2014 Elsevier Ltd. All rights reserved.
• US3963779A
  申请人：——

  公开号：US3963779A

  公开（公告）日：1976-06-15
• Ruthenium-Catalyzed Tertiary Amine Formation from Nitroarenes and Alcohols
  作者：Chao Feng、Yong Liu、Shengming Peng、Qi Shuai、Guojun Deng、Chao-Jun Li

  DOI：10.1021/ol1020527

  日期：2010.11.5

  A highly selective ruthenium-catalyzed C-N bond formation was developed by using the hydrogen-borrowing strategy. Various tertiary amines were obtained efficiently from nitroarenes and primary alcohols. The reaction tolerates a wide range of functionalities. A tentative mechanism was proposed for this direct amination reaction of alcohols with nitroarenes.
• Regioselective Synthesis of 2° Amides Using Visible-Light-Induced Photoredox-Catalyzed Nonaqueous Oxidative C–N Cleavage of <i>N</i>,<i>N</i>-Dibenzylanilines
  作者：Nalladhambi Neerathilingam、Mandapati Bhargava Reddy、Ramasamy Anandhan

  DOI：10.1021/acs.joc.1c01792

  日期：2021.11.5

  protocol on 2-(dibenzylamino)benzamide to afford quinazolinones with (NH4)2S2O8 as an additive. Mechanistic studies imply that the reaction might undergo in situ generation of α-amino radical to imine by C–N bond cleavage followed by the addition of superoxide ion to form amides.

  据报道，可见光驱动的光氧化还原催化的N , N -二苄基苯胺的非水氧化 C-N 裂解为 2° 酰胺。此外，我们已将此协议应用于 2-(二苄基氨基) 苯甲酰胺以提供具有 (NH 4 ) 2 S 2 O 8作为添加剂的喹唑啉酮。机理研究表明，该反应可能通过 C-N 键断裂，然后加入超氧离子形成酰胺，原位生成 α-氨基自由基为亚胺。