N-{1-[4-(trifluoromethyl)phenyl]ethyl}-4-methylaniline | 1041557-24-7

• 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-{1-[4-(trifluoromethyl)phenyl]ethyl}-4-methylaniline
• 英文别名: 4-methyl-N-[1-[4-(trifluoromethyl)phenyl]ethyl]aniline
• CAS: 1041557-24-7
• 化学式: C₁₆H₁₆F₃N
• 分子量: 279.305
• InChiKey: KELILWIRHTYAHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  p-Tolyl-[1-(4-trifluoromethyl-phenyl)-eth-(E)-ylidene]-amine 在 chloro(η5-cyclopentadienyl)(1,3-dimesitylimidazol-2-ylidene)nickel 、 NaH*C₆H₁₅B 、 二苯基硅烷 、 甲醇 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 以69%的产率得到N-{1-[4-(trifluoromethyl)phenyl]ethyl}-4-methylaniline
  参考文献：
  名称：

  Cyclopentadienyl N-heterocyclic carbene–nickel complexes as efficient pre-catalysts for the hydrosilylation of imines

  摘要：

  原位生成的镍氢化物[Ni(Mes2NHC)HCp]及其阳离子类似物[Ni(Mes2NHC)(NCMe)Cp](PF6)是在温和条件下进行醛亚胺和酮亚胺氢化反应的高效化学选择性前催化剂。

  DOI：

  10.1039/c3cy00514c

文献信息

• Rhodium catalysts with cofactor mimics for the biomimetic reduction of CN bonds
  作者：Jie Tang、Wenjin Dong、Fushan Chen、Li Deng、Mo Xian

  DOI：10.1039/d1cy00904d

  日期：——

  from a rhodium center to imine substrates in a biomimetic way. Under both transfer hydrogenation and reductive amination reaction conditions, the catalyst exhibited good selectivity towards CN bonds. With the catalyst, 34 imines were transfer hydrogenated to corresponding amines and a key intermediate of retigabine was prepared via reductive amination in a greener way. According to the NMR observations

  将基于金属和键合辅因子模拟物之间合作的策略应用于 CN 键的转移氢化。我们设计并合成了一种含有 1,3-二甲基苯并咪唑部分的铑配合物，它可以以仿生的方式将氢化物从铑中心转移到亚胺底物上。在转移氢化和还原胺化反应条件下，催化剂对C N 键表现出良好的选择性。使用该催化剂，34个亚胺被转移氢化成相应的胺，并通过还原胺化以更绿色的方式制备了瑞替加滨的关键中间体。根据核磁共振观察和同位素实验，提出了这种仿生还原碳氮键的合理机制。
• Amine Synthesis through Mild Catalytic Hydrosilylation of Imines using Polymethylhydroxysiloxane and [RuCl2(arene)]2 Catalysts
  作者：Bin Li、Jean-Baptiste Sortais、Christophe Darcel、Pierre H. Dixneuf

  DOI：10.1002/cssc.201100585

  日期：2012.2.13

  Tolerate silicone! The stable [RuCl2(p‐cymene]2 complex is an efficient catalyst for the direct chemoselective hydrosilylation of functionalized aldimines and ketimines into amines, using polymethylhydroxysiloxane as an inexpensive, stable, and safe hydrosilane source. The catalysis operates in ethanol, under air at room temperature, and tolerates the ketone ester and alkene functionality.

  耐硅胶！稳定的[RuCl 2（p- cymene）2络合物是一种有效的催化剂，可使用聚甲基羟基硅氧烷作为廉价，稳定且安全的氢化硅烷源，将官能化的亚胺和酮亚胺直接化学选择性氢化硅烷化为胺。在室温下，并能耐受酮酯和烯烃的官能团。
• A Highly Efficient Base-Metal Catalyst: Chemoselective Reduction of Imines to Amines Using An Abnormal-NHC–Fe(0) Complex
  作者：Mrinal Bhunia、Pradip Kumar Hota、Gonela Vijaykumar、Debashis Adhikari、Swadhin K. Mandal

  DOI：10.1021/acs.organomet.6b00478

  日期：2016.9.12

  A base-metal, Fe(0)-catalyzed hydrosilylation of imines to obtain amines is reported here which outperforms its noble-metal congeners with the highest TON of 17000. The catalyst, (aNHC)Fe(CO)(4), works under very mild conditions, with extremely low catalyst loading (down to 0.005 mol %), and exhibits excellent chemoselectivity. The facile nature of the imine reduction under mild conditions has been further demonstrated by reducing imines towards expensive commercial amines and biologically important N-alkylated sugars, which are difficult to achieve otherwise. A mechanistic pathway and the source of chemoselectivity for imine hydrosilylation have been proposed on the basis of the well-defined catalyst and isolable intermediates along the catalytic cycle.