N-benzyl-(3-trifluoromethylphenyl)amine | 404-64-8

• 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-(3-trifluoromethylphenyl)amine
• 英文别名: N-benzyl-3-(trifluoromethyl)benzenamine；N-(3-trifluoromethylphenyl)benzylamine；benzyl-(3-trifluoromethyl-phenyl)amine；benzyl-(3-trifluoromethylphenyl)amine；N-benzyl-3-(trifluoromethyl)aniline；N-[3-(trifluoromethyl)phenyl]benzylamine
• CAS: 404-64-8
• 化学式: C₁₄H₁₂F₃N
• mdl: MFCD00018031
• 分子量: 251.251
• InChiKey: LFFKRFUTMGWQPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2921420090

反应信息

• 作为反应物：
  描述：

  、 N-benzyl-(3-trifluoromethylphenyl)amine 以 二氯甲烷 为溶剂， 生成 2-{[benzyl-(3-trifluoromethyl-phenyl)-carbamoyl]-methylene}-malonic acid diethyl ester
  参考文献：
  名称：

  A Lewis-Acid Catalyzed Synthesis of Substituted Oxindole Derivatives

  摘要：

  Lewis acid-catalyzed cyclization of various 2-(N-arylcarbamoyl)-methylenemalonates to give nitrogen-containing benzo-annelated heterocycles was investigated in terms of selectivity. Reaction of substrates with various alkyl groups on nitrogen proceeded to give oxindole derivatives. Cyclization reaction of diester-amides of MeO and halooen-substituted anilines in the presence of catalytic Lewis acid (ZnCl2, SnCl4, AlCl3, Zn(OTf)(2), Sc(OTf)(3), etc.) gave oxindoles in high yields. Interesting regioselectivity was observed for meta- halogen substrates. Dimethoxyisoquinoline analogs were also obtained by this reaction using a catalytic Lewis acid.

  DOI：

  10.3987/com-05-s(t)25
• 作为产物：
  描述：

  苯甲醛 在 乙醇 、 铂 作用下， 生成 N-benzyl-(3-trifluoromethylphenyl)amine
  参考文献：
  名称：

  Kinetics of the Catalytic Hydrogenation of Certain Schiff Bases¹

  摘要：

  DOI：

  10.1021/ja01100a040

文献信息

• Room-Temperature Copper-Catalyzed Carbon-Nitrogen Coupling of Aryl Iodides and Bromides Promoted by Organic Ionic Bases
  作者：Chu-Ting Yang、Yao Fu、Yao-Bing Huang、Jun Yi、Qing-Xiang Guo、Lei Liu

  DOI：10.1002/anie.200903158

  日期：2009.9.21

  solubility alone does not explain the performance of organic ionic bases in the room‐temperature coupling of aryl iodides and even bromides with aliphatic and aromatic amines and N‐heterocycles (NuH; see scheme). Conductivity measurements show that these organic ionic bases, which contain tetraalkylammonium or ‐phosphonium cations, are readily ionized in organic solvents.

  仅仅良好的溶解度并不能解释有机离子碱在芳基碘化物甚至溴化物与脂族和芳族胺以及N杂环的室温偶联中的性能（NuH；参见方案）。电导率测量表明，这些含有四烷基铵或阳离子的有机离子碱在有机溶剂中很容易被电离。
• Copper-catalyzed formation of carbon-heteroatom and carbon-carbon bonds
  申请人：——

  公开号：US20030065187A1

  公开（公告）日：2003-04-03

  The present invention relates to copper-catalyzed carbon-heteroatom and carbon-carbon bond-forming methods. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of an amide or amine moiety and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In additional embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between a nitrogen atom of an acyl hydrazine and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In other embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of a nitrogen-containing heteroaromatic, e.g., indole, pyrazole, and indazole, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-oxygen bond between the oxygen atom of an alcohol and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. The present invention also relates to copper-catalyzed methods of forming a carbon-carbon bond between a reactant comprising a nucleophilic carbon atom, e.g., an enolate or malonate anion, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. Importantly, all the methods of the present invention are relatively inexpensive to practice due to the low cost of the copper comprised by the catalysts.

  本发明涉及铜催化的碳-杂原子和碳-碳键形成方法。在某些实施例中，本发明涉及铜催化的方法，用于在酰胺或胺基团的氮原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氮键。在其他实施例中，本发明涉及铜催化的方法，用于在酰基肼的氮原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氮键。在另一些实施例中，本发明涉及铜催化的方法，用于在含氮杂环芳烃（例如吲哚、吡唑和吲哌）的氮原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氮键。在某些实施例中，本发明涉及铜催化的方法，用于在醇的氧原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氧键。本发明还涉及铜催化的方法，用于在包含亲核碳原子的反应物（例如烯醇酸盐或丙二酸盐负离子）与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-碳键。重要的是，由于催化剂中铜的低成本，本发明的所有方法都相对廉价。
• New Ligands for Copper-Catalyzed CN Coupling Reactions at Gentle Temperature
  作者：Jinyue Su、Yatao Qiu、Sheng Jiang、Dayong Zhang

  DOI：10.1002/cjoc.201400147

  日期：2014.8

  Pyridin‐2‐ol‐N‐oxide was designed as an efficient ligand for the coupling reaction of aryl iodides, aryl bromides and aryl chlorides, respectively, with primary amines, cyclic secondary amines or N‐containing heterocycles at room or moderate temperature. The catalytic system showed great functional groups tolerance and excellent selective reactivity.

  吡啶-2-醇-N-氧化物被设计为在室温或中温下分别使芳基碘化物，芳基溴化物和芳基氯化物与伯胺，环状仲胺或含N杂环偶联反应的有效配体。催化体系显示出强大的官能团耐受性和出色的选择性反应性。
• Direct reductive amination of carbonyl compounds with primary/secondary amines using recyclable water-soluble FeII/EDTA complex as catalyst
  作者：Malhari D. Bhor、Mayur J. Bhanushali、Nitin S. Nandurkar、Bhalchandra M. Bhanage

  DOI：10.1016/j.tetlet.2007.12.023

  日期：2008.2

  Direct reductive amination of aliphatic, aromatic and heterocyclic carbonyl compounds with primary/secondary amines is reported with water-soluble FeII/EDTA complex as a catalyst using low-pressure molecular hydrogen in a biphasic media. The catalyst is highly selective, recyclable and is an excellent replacement for expensive noble metal catalysts or stoichiometric reducing agents.

  据报道，水溶性Fe II / EDTA络合物作为催化剂，使用低压分子氢在双相介质中，将伯，仲胺直接与脂肪族，芳香族和杂环羰基化合物进行还原性胺化反应。该催化剂具有高选择性，可回收利用，是昂贵的贵金属催化剂或化学计量还原剂的理想替代品。
• Insight into O₂-Promoted Base-Catalyzed<i>N</i>-Alkylation of Amines with Alcohols
  作者：Chao Wang、Changpeng Chen、Jian Han、Jingyu Zhang、Yingming Yao、Yingsheng Zhao

  DOI：10.1002/ejoc.201500086

  日期：2015.5

  efficient and practical transition-metal-free CsOH/O2 catalyst system was developed for the N-alkylation of amines with alcohols under argon. This strategy was compatible with many alcohols and exhibits excellent functional group tolerance. More significantly, the selective formation of secondary amines was achieved in excellent yields. The detailed mechanistic study gave a clear understanding of the role

  开发了一种高效实用的不含过渡金属的 CsOH/O2 催化剂体系，用于在氩气下用醇对胺进行 N-烷基化。该策略与许多醇相容，并表现出优异的官能团耐受性。更重要的是，仲胺的选择性形成以极好的收率实现。详细的机理研究清楚地了解了碱和氧在催化循环中的作用。