N-(4-bromobenzyl)-4-chloroaniline

• 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-(4-bromobenzyl)-4-chloroaniline
• 英文别名: N-[(4-bromophenyl)methyl]-4-chloroaniline
• 化学式: C₁₃H₁₁BrClN
• mdl: MFCD11144563
• 分子量: 296.594
• InChiKey: UQIPYOMBXPVFOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(4-bromobenzyl)-4-chloroaniline 在 dipotassium peroxodisulfate 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以45%的产率得到4-溴-N-(4-氯苯基)苯甲酰胺
  参考文献：
  名称：

  Sulfate Radical Anion (SO₄^•–) Mediated C(sp³)–H Nitrogenation/Oxygenation in N-Aryl Benzylic Amines Expanded the Scope for the Synthesis of Benzamidine/Oxazine Heterocycles

  摘要：

  A transition-metal-free, K2S2O8-mediated intra-molecular, oxidative nitrogenation/oxygenation of C(sp(3))-H in N-aryl benzylic amines followed by oxidation at the benzylic center has been developed for the synthesis of benzamidine/benzoxazine heterocycles, providing an expedient access to quinazolin-4(3H)-ones, N-aryl-2-arylbenzimidazoles, and 4H-3,1-benzoxazin-4-ones. A considerable amount of work dealing with the mechanistic study to understand the crucial intramolecular cyclization step largely favors an iminium ion as the key intermediate.

  DOI：

  10.1021/acs.joc.5b01872
• 作为产物：
  描述：

  1-(4-溴苯基)-N-(4-氯苯基)甲亚胺 在 甲醇 、 sodium tetrahydroborate 作用下， 生成 N-(4-bromobenzyl)-4-chloroaniline
  参考文献：
  名称：

  Synthesis of N-benzyl-N-phenylthiophene-2-carboxamide analogues as a novel class of enterovirus 71 inhibitors

  摘要：

  一系列N-苄基-N-苯基噻吩-2-羧酰胺类似物被确定为新型人类肠道病毒71抑制剂，EC50值高达1.42μM。

  DOI：

  10.1039/c5ra07286g

文献信息

• Switchable Bifunctional Bistate Reusable ZnO–Cu for Selective Oxidation and Reduction Reaction
  作者：Kasturi Sarmah、Subhamoy Mukhopadhyay、Tarun K. Maji、Sanjay Pratihar

  DOI：10.1021/acscatal.8b03785

  日期：2019.1.4

  copper loaded zinc oxide (ZnO–Cu) for its stimuli (O2/light) responsive switchable performance between its reduced (S-1) and oxidized (S-2) state for two antagonistic reactions, namely oxidation of alkyl arenes/heteroarenes to aldehydes/ketones and reduction of nitro arenes/heteroarenes to corresponding amines. The two states of the catalyst showed its switchable performance as highly active and poorly

  在这里，我们公开了利用铜负载的氧化锌（ZnO-Cu）在两个还原反应（即氧化）的还原（S-1）和氧化（S-2）状态之间的刺激（O 2 /光）响应可转换性能。将烷基芳烃/杂芳烃还原为醛/酮，并将硝基芳烃/杂芳烃还原为相应的胺。催化剂的两种状态均显示出其可切换的性能，即用于氧化和还原的高活性和低活性催化剂，并且通过改变刺激（光和O 2 / N 2），两个反应都可以“关闭”和“打开”。）。发现状态之间的转换效率及其相对反应性在各种反应条件下均保持一致，并且无论氧化还原顺序（反之亦然）和反应中使用的底物如何，都保持不变。光催化剂（S-1和S-2）表现出良好的催化活性，多种可重复使用性，广泛的底物范围以及对两种反应均具有合理的官能团耐受性，并在大规模应用中探索了其质量性能。该系统被用于辅助串联催化装置中，用于通过催化状态之间的刺激响应切换而利用氧化和还原反应两者来合成苄胺。
• Cross-dehydrogenative coupling strategy for phosphonation and cyanation of secondary N-alkyl anilines by employing 2,3-dichloro-5,6-dicyanobenzoquinone
  作者：Qing Liu、Shuchen Yu、Liangzhen Hu、Muhamad Ijaz Hussain、Xiaohui Zhang、Yan Xiong

  DOI：10.1016/j.tet.2018.10.058

  日期：2018.12

  has been developed firstly under mild reaction conditions. Based on detailed optimization of reaction conditions, the substrate generality of N-alkyl anilines and various hydrogen phosphonates has been investigated, and a series of versatile α-aminophosphonates and α-aminonitriles were therefore furnished in good to excellent yields. A plausible collective reaction mechanism through dehydrogenation to

  首先在温和的反应条件下开发了无金属的膦酸和仲N-烷基苯胺氰化的交叉脱氢偶联策略。在详细优化反应条件的基础上，研究了N-烷基苯胺和各种膦酸氢盐的底物通用性，因此提供了一系列通用的α-氨基膦酸酯和α-氨基腈，收率良好至优异。提出了通过脱氢形成亚胺，然后分别形成α-氨基膦酸酯和α-氨基腈的合理的集体反应机理。
• Regioselective Nitration of <i>N</i>-Alkyl Anilines using <i>tert</i>-Butyl Nitrite under Mild Condition
  作者：Priyanka Chaudhary、Surabhi Gupta、Nalluchamy Muniyappan、Shahulhameed Sabiah、Jeyakumar Kandasamy

  DOI：10.1021/acs.joc.8b02377

  日期：2019.1.4

  Regioselective ring nitration of N-alkyl anilines is reported using tert-butyl nitrite. The reactions proceed efficiently with a wide range of substrates providing synthetically useful N-nitroso N-alkyl nitroanilines in excellent yields which can be easily converted into N-alkyl phenylenediamines and N-alkyl nitroanilines using Zn-AcOH and HCl/MeOH, respectively.

  据报道使用亚硝酸叔丁酯对N-烷基苯胺的区域选择性环硝化。该反应在多种底物下有效地进行，以优异的产率提供了合成上有用的N-亚硝基N-烷基硝基苯胺，可以分别使用Zn-AcOH和HCl / MeOH轻松地将其转化为N-烷基苯二胺和N-烷基硝基苯胺。
• Catalyst-free Alkylation of Aromatic Amines with Aldehydes
  作者：Qi He、Zhouyu Wang、Shan Qian、Zhenju Jiang、Jianhui Li、Dehong Jiang、Wensi Ai

  DOI：10.2174/1570178611310050012

  日期：2013.5.1

  In the absence of any additional catalysts, a series of aromatic amines were alkylated with a range of aromatic and aliphatic aldehydes. Moderate to excellent isolated yields (up to 94%) were obtained under mild conditions. Simultaneously, the reaction time dramatically shortened from hours to minutes when the Microwave technique was used.

  在没有任何额外催化剂的情况下，一系列芳香胺与多种芳香和脂肪醛进行了烷基化反应。在温和条件下获得了中等到优异的分离产率（最高可达94%）。与此同时，当使用微波技术时，反应时间从几个小时缩短到了几分钟。
• Selective reductive amination of aldehydes from nitro compounds catalyzed by molybdenum sulfide clusters
  作者：E. Pedrajas、I. Sorribes、K. Junge、M. Beller、R. Llusar

  DOI：10.1039/c7gc01603d

  日期：——

  amines are selectively obtained from low value starting materials using hydrogen and a non-noble metal-based catalyst. The reductive amination of aldehydes from nitroarenes or nitroalkanes is efficiently catalyzed by a well-defined diamino molybdenum sulfide cluster in a one-pot homogeneous reaction. The integrity of the molecular cluster catalyst is preserved along the process.

  仲胺是使用氢和非贵金属基催化剂从低价原料中选择性获得的。一锅均相反应中，明确定义的二氨基硫化钼簇有效催化了硝基芳烃或硝基烷烃中醛的还原胺化反应。分子簇催化剂的完整性在此过程中得以保留。