N,N-二苄基-3-甲基苯胺 | 55197-79-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N,N-二苄基-3-甲基苯胺
• 英文名称: N,N-dibenzyl-3-methylaniline
• CAS: 55197-79-0
• 化学式: C₂₁H₂₁N
• 分子量: 287.404
• InChiKey: ARABZLFYTAEJHG-UHFFFAOYSA-N

物化性质

• 熔点：
  78 °C
• 沸点：
  229 °C(Press: 10 Torr)
• 密度：
  1.0265 g/cm3(Temp: 80 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 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-二苄基-3-甲基苯胺 在 palladium on activated charcoal 乙酸铵 、 盐酸 、 lithium aluminium tetrahydride 、 氢气 、 溴 、 溶剂黄146 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 反应 10.0h， 生成 N-[4-(2-acetamidopropyl)-2-bromo-5-methylphenyl]acetamide
  参考文献：
  名称：

  Selective monoamine oxidase inhibitors. 4. 4-Aminophenethylamine derivatives with neuron-selective action

  摘要：

  Nine 4-aminophenethylamine derivatives were synthesized and tested for monoamine oxidase (MAO) inhibitory effects with particular attention to their selectivity for MAO within monoaminergic neurons in the rat brain. All compounds selectively inhibited the A form of MAO in vitro. Some of the compounds inhibited the MAO within the monoaminergic neurons at much lower doses than those required for inhibition of MAO within other cells in vivo. The most potent compounds in this respect were 4-amino-2-fluoro-alpha-methylphenethylamine (5) and 4-amino-2-chloro-alpha-methylphenethylamine (4).

  DOI：

  10.1021/jm00161a020
• 作为产物：
  描述：

  氯化苄 、 3-甲基苯胺 在 碘 、 sodium acetate 作用下， 生成 N,N-二苄基-3-甲基苯胺
  参考文献：
  名称：

  Kent et al., Journal of the Chemical Society, 1939, p. 1858,1861

  摘要：

  DOI：

文献信息

• Direct One‐Pot Reductive N‐Alkylation of Nitroarenes by using Alcohols with Supported Gold Catalysts
  作者：Chun‐Hong Tang、Lin He、Yong‐Mei Liu、Yong Cao、He‐Yong He、Kang‐Nian Fan

  DOI：10.1002/chem.201100393

  日期：2011.6.20

  Gold standard support! The direct reductive mono‐ or di‐N‐alkylation of aromatic nitro compounds with alcohols, using a hydrogen‐borrowing strategy, was efficiently promoted by a ligand‐free titania‐supported gold catalyst system (see scheme). A variety of nitroarenes were selectively converted into the corresponding secondary or tertiary amines in good to excellent yields without any co‐catalysts

  黄金标准支持！不含氢的二氧化钛负载的金催化剂体系有效地促进了使用氢借用策略使芳香族硝基化合物与醇直接还原成单-或二-N-烷基化反应（参见方案）。在不使用任何助催化剂（例如碱和稳定配体）的情况下，可以将各种硝基芳烃以良好的优良性能选择性地转化为相应的仲胺或叔胺。
• Reductive Alkylation of Azides and Nitroarenes with Alcohols: A Selective Route to Mono- and Dialkylated Amines
  作者：Ishani Borthakur、Milan Maji、Abhisek Joshi、Sabuj Kundu

  DOI：10.1021/acs.joc.1c02625

  日期：2022.1.7

  Herein, we demonstrated an efficient protocol for reductive alkylation of azides/nitro compounds via a borrowing hydrogen (BH) method. By following this protocol, selective mono- and dialkylated amines were obtained under mild and solvent-free conditions. A series of control experiments and deuterium-labeling experiments were performed to understand this catalytic process. Mechanistic studies suggested

  在这里，我们展示了一种通过借氢 (BH) 方法对叠氮化物/硝基化合物进行还原烷基化的有效方案。通过遵循该协议，在温和且无溶剂的条件下获得了选择性的单烷基化胺和二烷基化胺。进行了一系列对照实验和氘标记实验以了解这一催化过程。机理研究表明，Ir(III)-H 是该反应的活性中间体。KIE 研究表明，酒精的 C-H 键断裂可能是限速步骤。值得注意的是，这种无溶剂策略揭示了大约 5600 的高 TON。基于动力学研究和控制实验，提出了一种金属-配体协同机制。
• Synthesis of Benzidine Derivatives via FeCl₃·6H₂O-Promoted Oxidative Coupling of Anilines
  作者：Xuege Ling、Yan Xiong、Ruofeng Huang、Xiaohui Zhang、Shuting Zhang、Changguo Chen

  DOI：10.1021/jo4002504

  日期：2013.6.7

  Under open-flask conditions in the presence of commercially available FeCl3·6H2O, N,N-disubstituted anilines can be converted into diversely functionalized benzidines with yields of up to 99%. Oxidative coupling was extended to N-monosubstituted anilines, and the method was applied to the efficient preparation of 6,6′-biquinoline. Mechanistic investigations have also been performed to explain the observed

  在烧瓶条件下，在可商购的FeCl 3 ·6H 2 O的存在下，N，N-二取代苯胺可以转化为功能多样的联苯胺，收率最高为99％。氧化偶联作用扩展至N-单取代苯胺，并将该方法用于有效制备6,6'-联喹啉。还进行了机械研究以解释观察到的反应性。
• Aqueous-MediatedN-Alkylation of Amines
  作者：Chingakham B. Singh、Veerababurao Kavala、Akshaya K. Samal、Bhisma K. Patel

  DOI：10.1002/ejoc.200600937

  日期：2007.3

  Direct N-alkylation of primary amines to secondary/tertiary amines and of secondary amines to tertiary amines has been achieved in excellent yields by employing alkyl, benzylic and allylic halides in the presence of NaHCO3 in an aqueous medium at an elevated temperature. Amines of different stereoelectronic nature react with ease with different halides. The selective formation of secondary amines and

  伯胺直接 N-烷基化为仲/叔胺和仲胺直接 N-烷基化为叔胺，通过使用烷基、苄基和烯丙基卤化物，在 NaHCO3 存在下，在水性介质中，在升高的温度下，以极好的收率实现。不同立体电子性质的胺容易与不同的卤化物反应。仲胺的选择性形成和三种不同取代的叔胺的形成是一些
• Selective N-Alkylation of Amines with Alcohols by Using Non-Metal-Based Acid-Base Cooperative Catalysis
  作者：Ya Du、Shunsuke Oishi、Susumu Saito

  DOI：10.1002/chem.201102446

  日期：2011.10.24

  straightforward method for the selective N‐mono‐ and dialkylation of amines with alcohols by means of non‐metal‐based catalysis promoted by TAPC is reported (see scheme). Selectivity of the N‐mono‐ and dialkylation, substrate scope and functional‐group tolerance are highlighted with respect to each amine (1° and 2°; aromatic and aliphatic) and alcohol (1°, 2° and 3°; benzylic and aliphatic) component.

  学会合作：通过TAPC促进的基于非金属的催化方法，报道了一种直接的胺与醇选择性地将胺与醇进行N-单-和二烷基化的方法（参见方案）。针对每种胺（1°和2°；芳族和脂肪族）和醇（1°，2°和3°；苄基和脂肪族），重点介绍了N-单烷基和二烷基化的选择性，底物范围和官能团耐受性） 成分。