N-(二苯基亚甲基)-4-硝基苯胺 | 35393-20-5

• 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-(二苯基亚甲基)-4-硝基苯胺
• 英文名称: N-(diphenylmethylene)-4-nitroaniline
• 英文别名: N-(Diphenylmethylen)-p-nitroanilin；Benzophenon-p-nitrophenylimin；N-benzhydrylidene-4-nitro-aniline；N-Diphenylmethylen-4-nitro-anilin；N-Benzhydryliden-4-nitro-anilin；Benzophenon-(4-nitro-anil)；N-(4-nitrophenyl)-1,1-diphenylmethanimine
• CAS: 35393-20-5
• 化学式: C₁₉H₁₄N₂O₂
• 分子量: 302.332
• InChiKey: UBFYKRUAAWHJTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(二苯基亚甲基)-4-硝基苯胺 在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 4-硝基苯胺
  参考文献：
  名称：

  使用二苯甲酮亚胺的钯催化芳基溴化物转化为伯苯胺的温和条件

  摘要：

  描述了使用Pd催化胺化策略将芳基溴化物温和（30°C）和有效（53-91％）转化为伯苯胺的过程。本文描述了配体优化，碱和溶剂选择以及该方法的一般底物范围的详细说明。

  DOI：

  10.1016/j.tetlet.2009.01.091
• 作为产物：
  描述：

  2-(Diphenylmethylen)-4-p-nitrophenylbenzhydrazidin 以90%的产率得到
  参考文献：
  名称：

  BUZYKIN B. I.; LEZHNINA G. D.; KITAEV YU. P., ZH. ORGAN. XIMII , 1975, 11, HO 4, 848-853

  摘要：

  DOI：

文献信息

• Facile Synthesis of Triarylmethanimine Promoted by a Lewis Acid - Base Pair: Theoretical and Experimental Studies
  作者：Yan Liu、Qiwu Yang、Dongling Hao、Wenqin Zhang

  DOI：10.1071/ch12090

  日期：——

  An efficient method for triarylmethanimine synthesis promoted by a Lewis acid–base pair (AlCl3–Et3N) was designed using mechanistic analysis with the aid of density functional theory. A series of triarylmethanimines were successfully prepared under mild conditions in good to excellent yields with a simple work-up procedure. The promoter, the Lewis acid–base pair (AlCl3–Et3N), is inexpensive, efficient, and shows good functional group tolerance. The experimental results show that the electronic effect played a significant role, i.e. the reactions proceeded smoothly when electron-sufficient arylamines and electron-deficient ketones were used as substrates.

  在密度泛函理论的帮助下，利用机理分析设计了一种由路易斯酸碱对（AlCl3-Et3N）促进的三芳基甲亚胺的高效合成方法。通过简单的操作步骤，在温和的条件下成功地制备了一系列三芳基甲亚胺，产率从良好到极佳。路易斯酸碱对（AlCl3-Et3N）是一种廉价、高效且具有良好官能团耐受性的促进剂。实验结果表明，电子效应发挥了重要作用，即当使用电子充足的芳胺和电子不足的酮作为底物时，反应进展顺利。
• An expedient one-pot synthesis of benzophenone Schiff bases from benzene
  作者：Irena S. Akhrem、Lyudmila V. Afanas’eva、Dzhul’etta V. Avetisyan、Oleg I. Artyushin、Nikolai D. Kagramanov

  DOI：10.1016/j.mencom.2020.03.037

  日期：2020.3

  A simple and efficient one-pot synthesis of benzophenone Schiff bases from benzene, CCl4 and aromatic amines was developed based on the the reaction of benzene with CCl4·AlCl3 complex. This method affords Ph2CCl2 as well as the products of its subsequent reaction with aromatic amines, benzophenone Schiff bases, selectively and in good yields.

  基于苯与CCl4·AlCl3配合物的反应，开发了一种简单，高效的一锅法从苯，CCl4和芳族胺合成二苯甲酮席夫碱。该方法选择性地且高收率地提供了Ph2CCl2及其随后与芳族胺，二苯甲酮席夫碱的反应产物。
• Amination of Benzylic CH Bonds by Arylazides Catalyzed by CoII–Porphyrin Complexes: A Synthetic and Mechanistic Study
  作者：Fabio Ragaini、Andrea Penoni、Emma Gallo、Stefano Tollari、Claudia Li Gotti、Marta Lapadula、Enrica Mangioni、Sergio Cenini

  DOI：10.1002/chem.200390018

  日期：2003.1.3

  the Co(II)-porphyrin complex. This unstable adduct can either react with the hydrocarbon in the rate-determining step or decompose by a unimolecular mechanism to afford a putative "nitrene" complex, which reacts with more azide, but not with the hydrocarbon, to afford the byproduct diaryldiazene. The kinetics of the catalytic reaction have been investigated for a range of azides and substituted toluenes

  Co（II）-卟啉配合物催化芳香族叠氮化物（ArN（3））与含有苄基（ArR（1）R（2）CH）的烃的反应，得到相应的胺（ArR（1）R（2 C-NHAr）。当R取代基中的至少一个是氢时，催化反应进一步进行以高收率得到亚胺ArRC ＝ NAr。已经研究了反应机理。该反应通过芳基叠氮化物与Co（II）-卟啉配合物的可逆配位而进行。这种不稳定的加合物可以在速率确定步骤中与烃反应，或者通过单分子机理分解，以提供推定的“硝烯”络合物，该络合物与更多的叠氮化物反应，但不与烃反应，从而产生副产物二芳基二氮杂。对于一系列叠氮化物和取代的甲苯，已经研究了催化反应的动力学。具有吸电子取代基的芳基叠氮化物以更快的速度反应，并且在log（k）和Taft参数之间发现了良好的相关性。另一方面，发现相对于甲苯的对甲苯的取代率的对数与单独的自由基参数（sigma * JJ）之间具有极好的相关性，而极性参数没有显着贡献。
• Amination of benzylic C–H bonds by aryl azides catalysed by CoII(porphyrin) complexes. A new reaction leading to secondary amines and imines
  作者：Sergio Cenini、Emma Gallo、Andrea Penoni、Fabio Ragaini、Stefano Tollari

  DOI：10.1039/b006136k

  日期：——

  CoII(porphyrin) complexes catalyse the reaction of aromatic azides, ArN3, with hydrocarbons containing a benzylic group, R1R2R3CH, to give the corresponding amines, R1R2R3C-NHAr. When at least one of the R1–R3 substituents is hydrogen, the catalytic reaction proceeds further to give the imines R1R2CNAr in good yields.

  CoII(卟啉)配合物催化芳族叠氮化物ArN3与含有苄基R1R2R3CH的烃反应生成相应的胺R1R2R3C-NHAr。当至少一个 R1-R3 取代基是氢时，催化反应进一步进行，以良好的收率得到亚胺 R1R2CNAr。
• Simple, Efficient Catalyst System for the Palladium-Catalyzed Amination of Aryl Chlorides, Bromides, and Triflates
  作者：John P. Wolfe、Hiroshi Tomori、Joseph P. Sadighi、Jingjun Yin、Stephen L. Buchwald

  DOI：10.1021/jo991699y

  日期：2000.2.1

  Palladium complexes supported by (o-biphenyl)P(t-Bu)(2) (3) or (o-biphenyl)PCy2 (4) are efficient catalysts for the catalytic amination of a wide variety of aryl halides and triflates. Use of ligand 3 allows for the room-temperature catalytic amination of many aryl chloride, bromide, and triflate substrates, while ligand 4 is effective for the amination of functionalized substrates or reactions of acyclic secondary amines. The catalysts perform well for a large number of different substrate combinations at 80-110 degrees C, including chloropyridines and functionalized aryl halides and triflates using 0.5-1.0 mol % Pd; some reactions proceed efficiently at low catalyst levels (0.05 mol % Pd). These ligands are effective for almost all substrate combinations that have been previously reported with various other ligands, and they represent the most generally effective catalyst system reported to date. Ligands 3 and 4 are air-stable, crystalline solids that are commercially available. Their effectiveness is believed to be due to a combination of steric and electronic properties that promote oxidative addition, Pd-N bond formation, and reductive elimination.