N-(diphenylmethylene)-4-(trifluoromethyl)aniline | 1204601-39-7

• 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-(diphenylmethylene)-4-(trifluoromethyl)aniline
• 英文别名: 1,1-diphenyl-N-(4-(trifluoromethyl)phenyl)methanimine；1,1-diphenyl-N-[4-(trifluoromethyl)phenyl]methanimine
• CAS: 1204601-39-7
• 化学式: C₂₀H₁₄F₃N
• 分子量: 325.333
• InChiKey: JWMBQBKVWBUEFI-UHFFFAOYSA-N

物化性质

• 沸点：
  385.5±42.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(diphenylmethylene)-4-(trifluoromethyl)aniline 在 (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以87%的产率得到N-benzhydryl-4-(trifluoromethyl)aniline
  参考文献：
  名称：

  分批和连续流动的二丙胺的光催化和化学选择性转移加氢

  摘要：

  描述了用于间歇和连续流动的亚胺化学选择性转移氢化的可见光光催化方法。该反应利用Et 3 N作为氢源和单电子供体，从而能够选择性还原衍生自含有其他可还原官能团（包括腈，卤化物，酯和酮）的二芳基酮亚胺的亚胺。Et 3 N的双重作用已通过荧光猝灭测量，瞬态吸收光谱和氘标记研究得到了证实。连续流处理有助于直接扩大反应规模。

  DOI：

  10.1021/acs.orglett.7b03565
• 作为产物：
  描述：

  1-(diphenylmethylene)amino-1,2-benziodoxol-3-(1H)-one 、 4-三氟甲基苯硼酸 在 水 、 copper(I) bromide 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以65%的产率得到N-(diphenylmethylene)-4-(trifluoromethyl)aniline
  参考文献：
  名称：

  铜催化芳基（烯基）硼酸与含氮高价碘 (III) 试剂的亲电胺化

  摘要：

  开发了一种铜催化的芳基（烯基）硼酸的亲电N-亚胺化反应，该反应使用含有可转移（二芳基亚甲基）氨基的稳定高价碘 (III) 试剂。亲电C-N的交叉偶联反应在室温下顺利地进行氧化剂-自由和无碱基的条件下，其特征还在于由广泛的官能团的相容性下，其延伸的Ñ -electrophile亲电C-N交的范围在N -O 和N -Cl 试剂限制之外进行偶联。

  DOI：

  10.1002/adsc.202100594

文献信息

• Buchwald-Hartwig Amination of (Hetero)aryl Chlorides by Employing Mor-DalPhos under Aqueous and Solvent-Free Conditions
  作者：Bennett J. Tardiff、Mark Stradiotto

  DOI：10.1002/ejoc.201200510

  日期：2012.7

  catalyst system in the Buchwald–Hartwig amination of (hetero)aryl chlorides with primary or secondary amines conducted either under aqueous conditions without the use of co-solvents and/or surfactants or under solvent-free conditions (52 examples). We have established that reactions of this type can be conducted without the rigorous exclusion of air, and in the case of the solvent-free reactions, we have

  我们报告了 [Pd(cinnamyl)Cl]2/Mor-DalPhos 催化剂体系在（杂）芳基氯化物与伯胺或仲胺的 Buchwald-Hartwig 胺化中的应用，该胺化反应在水性条件下进行，不使用共溶剂和/或表面活性剂或在无溶剂条件下（52 个例子）。We have established that reactions of this type can be conducted without the rigorous exclusion of air, and in the case of the solvent-free reactions, we have demonstrated that appropriately selected liquid and solid reagents can be employed successfully.
• A facile access for the C-N bond formation by transition metal-free oxidative coupling of benzylic C-H bonds and amides
  作者：Jie Liu、Heng Zhang、Hong Yi、Chao Liu、Aiwen Lei

  DOI：10.1007/s11426-015-5381-2

  日期：2015.8

  as the oxidant, we communicate an efficient oxidative C-N coupling of benzylic C-H bonds with amides to afford a series of amination products in good yields. A wide range of functional groups as well as various sulfonamides and carboxamides are well tolerated. Moreover, this reaction involves both the challenging C-H functionalization and C-N bond formation.

  使用2,3-二氯-5,6-二氰基对苯醌（DDQ）作为氧化剂，我们传达了苄基CH键与酰胺的有效氧化CN偶联，以高收率提供了一系列胺化产品。广泛耐受各种官能团以及各种磺酰胺和羧酰胺。而且，该反应涉及具有挑战性的CH官能化和CN键的形成。
• Selective Synthesis of Polysubstituted Dihydroquinolines and α,β-Unsaturated Amidines by a Catalytic Reaction of Ynamides with Ketimines
  作者：Kiyosei Takasu、Yuusuke Kuroda、Naoya Shindoh、Yoshiji Takemoto

  DOI：10.1055/s-0033-1339191

  日期：——

  amidines. Ynamides reacted with benzophenone imines in the presence of triflic imide as a catalyst. Ynamides bearing a sulfonamide moiety gave the corresponding 2-amino-3,4-dihydroquinolines selectively in good to high yields. In contrast, yne-carbamates gave the corresponding α,β-unsaturated amidines exclusively. These methods permit simple preparation of sterically crowded polysubstituted quinolines and

  摘要 在三氟甲酰亚胺作为催化剂的存在下，酰胺与二苯甲酮亚胺反应。带有磺酰胺部分的酰胺选择性地以高产率至高产率产生了相应的2-氨基-3，4-二氢喹啉。相反，炔基氨基甲酸酯仅给出相应的α，β-不饱和am。这些方法允许简单地制备空间上拥挤的多取代喹啉和α，β-不饱和am。 在三氟甲酰亚胺作为催化剂的存在下，酰胺与二苯甲酮亚胺反应。带有磺酰胺部分的酰胺选择性地以高产率至高产率产生了相应的2-氨基-3，4-二氢喹啉。相反，炔基氨基甲酸酯仅给出相应的α，β-不饱和am。这些方法允许简单地制备空间上拥挤的多取代喹啉和α，β-不饱和am。
• Hydride, Hydrogen, Proton, and Electron Affinities of Imines and Their Reaction Intermediates in Acetonitrile and Construction of Thermodynamic Characteristic Graphs (TCGs) of Imines as a “Molecule ID Card”
  作者：Xiao-Qing Zhu、Qiao-Yun Liu、Qiang Chen、Lian-Rui Mei

  DOI：10.1021/jo902332n

  日期：2010.2.5

  A series of 61 imines with various typical structures were synthesized, and the thermodynamic affinities (defined as enthalpy changes or redox potentials in this work) of the imines to abstract hydride anions, hydrogen atoms, and electrons, the thermodynamic affinities of the radical anions of the imines to abstract hydrogen atoms and protons, and the thermodynamic affinities of the hydrogen adducts of the imines to abstract electrons in acetonitrile were determined by using titration calorimetry and electrochemical methods. The pure heterolytic and homolytic dissociation energies of the C = N pi-bond in the imines were estimated. The polarity of the C = N double bond in the imines was examined using a linear free-energy relationship. The idea of a thermodynamic characteristic graph (TCG) of imines as an efficient "Molecule ID Card" was introduced. The TCG can be used to quantitatively diagnose and predict the characteristic chemical properties of imines and their various reaction intermediates as well as the reduction mechanism of the imines. The information disclosed in this work could not only supply a gap of thermodynamics for the chemistry of imines but also strongly promote the fast development of the applications of imines.
• Correction to Photocatalytic and Chemoselective Transfer Hydrogenation of Diarylimines in Batch and Continuous Flow
  作者：Dean J. van As、Timothy U. Connell、Martin Brzozowski、Andrew D. Scully、Anastasios Polyzos

  DOI：10.1021/acs.orglett.8b02023

  日期：2018.7.20