N-(1-(4-nitrophenyl)ethyl)aniline

• 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-nitrophenyl)ethyl)aniline
• 英文别名: N-[1-(4-nitrophenyl)ethyl]aniline
• 化学式: C₁₄H₁₄N₂O₂
• mdl: MFCD11534064
• 分子量: 242.277
• InChiKey: WUONRFRPAIGYCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 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：
  57.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(1-(4-nitrophenyl)ethyl)aniline 在 potassium hydride 作用下， 以 乙腈 为溶剂， 反应 0.33h， 生成
  参考文献：
  名称：

  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”

  摘要：

  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.

  DOI：

  10.1021/jo902332n
• 作为产物：
  描述：

  [1-(4-Nitro-phenyl)-eth-(E)-ylidene]-phenyl-amine 在 苯硅烷 、 dichloro-[1-(3-methoxybenzyl)-3-(methyl)benzimidazole-2-ylidene](p-cymene)ruthenium(II) 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以93%的产率得到N-(1-(4-nitrophenyl)ethyl)aniline
  参考文献：
  名称：

  N-杂环碳烯络合物用于亚胺的化学选择还原和醛和酮的还原胺化

  摘要：

  在室温下，通过束缚和不束缚的半三明治钌N-杂环卡宾（NHC）络合物可有效催化亚胺化学选择性还原为仲胺。未束缚的Ru-NHC络合物比束缚的络合物作为减少醛亚胺和酮亚胺的催化剂更有效。使用最好的无束缚配合物作为催化剂，使用一系列亚胺探讨了对反应的电子和空间要求。通过以多种方式进行分子间和分子内竞争反应，测试了催化剂对亚胺还原的化学选择性。该催化剂在厌氧条件下具有很高的TON和TOF。

  DOI：

  10.1002/ejic.202000069

文献信息

• Direct and indirect reductive amination of aldehydes and ketones with solid acid-activated sodium borohydride under solvent-free conditions
  作者：Byung Tae Cho、Sang Kyu Kang

  DOI：10.1016/j.tet.2005.04.039

  日期：2005.6

  A simple and convenient procedure for reductive amination of aldehydes and ketones using sodium borohydride activated by boric acid, p-toluenesulfonic acid monohydrate or benzoic acid as reducing agent under solvent-free conditions is described.

  描述了一种简单方便的程序，用于在无溶剂条件下，使用硼酸，对甲苯磺酸一水合物或苯甲酸作为还原剂活化的硼氢化钠还原性胺化醛和酮。
• 糖衍生的氨基醇催化亚胺还原的方法
  申请人：浙江大学

  公开号：CN103936596B

  公开（公告）日：2016-02-03

  本发明公开了一种糖衍生的氨基醇催化亚胺还原的方法：以亚胺为底物，依次包括以下步骤：1）、将亚胺和糖衍生的氨基醇催化剂溶于有机溶剂Ⅰ中，所述亚胺和糖衍生的氨基醇催化剂的摩尔比为100:1～20；2）、向步骤1）所得的溶液中滴加1.5～5倍当量的三氯硅烷后，于-20～40℃下搅拌反应12～36h后，然后用饱和碳酸氢钠溶液淬灭；3）、将步骤2）的所得物用有机溶剂Ⅱ萃取，柱层析分离，制得胺类化合物。
• l-Pipecolinic acid derived Lewis base organocatalyst for asymmetric reduction of N-aryl imines by trichlorosilane: effects of the side amide group on catalytic performances
  作者：Zhouyu Wang、Chao Wang、Li Zhou、Jian Sun

  DOI：10.1039/c2ob26772a

  日期：——

  A series of N-formamides derived from pipecolinic acid have been synthesized and tested as Lewis base catalysts for the enantioselective reduction of N-aryl imines by trichlorosilane. Through the investigation of the structure–efficacy relationship between the side amide group and catalytic performance, several highly effective catalysts were discovered. In particular, arylamido-type catalyst 5i and

  衍生自一系列的N-甲酰胺胡椒酸已合成并测试了路易斯碱催化剂，可通过以下方法对映选择性还原N-芳基亚胺三氯硅烷。通过研究侧酰胺基与催化性能之间的结构-效率关系，发现了几种高效催化剂。特别地，芳基酰胺基型催化剂5i和非芳基酰胺基型催化剂6c表现出高反应性和对映选择性，以高分离产率（最高98％）和ee值（最高90％）降低了多种N-芳基亚胺的还原。96％）。此外，这两种催化剂在其对非芳族酮亚胺和非甲基酮亚胺的耐受性方面彼此互补。
• Zinc Chloride Mediated Nucleophilic Substitution: Amination and Thioetherification of Alcohols at Room Temperature
  作者：Ashima Singh、Shruti Gupta、Jitender M. Khurana

  DOI：10.1080/00304948.2020.1716617

  日期：2020.3.3

  Catalytic chemistry is one of the focal points for the development of environmentally benign organic transformations. It is true that the employment of catalysts in organic transformations comes wi...

  催化化学是开发环境友好型有机转化的重点之一。确实，在有机转化中使用催化剂是...
• Catalytic Mechanism Study on the 1,2‐ and 1,4‐Transfer Hydrogenation of Ketimines and β‐Enamino Esters Catalyzed by Axially Chiral Biscarboline‐Based Alcohols
  作者：Mengxian Dong、Jie Wang、Shijie Wu、Yang Zhao、Yangyang Ma、Yongfei Xing、Fei Cao、Longfei Li、Zhenqiu Li、Huajie Zhu

  DOI：10.1002/adsc.201900665

  日期：2019.10.8

  Axial N‐O alcohols, which have two large carboline moieties connected to the axis were synthesized and used in catalytic enantioselective 1,2‐ and 1,4‐transfer hydrogenations of total 26 ketimines and β‐enamino esters. Excellent levels of enantioselectivity ranging from 91% to 99% were achieved by using catalyst (aS)‐(S)‐3,3′‐bis((S)‐2‐(hydroxymethyl)pyrrolidine‐1‐carbonyl)‐9,9′‐dimethyl‐9H,9′H‐[1

  合成了具有两个与轴连接的大碳环部分的轴向N- O醇，并将其用于催化总共26种酮亚胺和β-烯胺酸酯的对映选择性1,2-和1,4-转移氢化。对映选择性为91％至99％的优异的水平通过使用催化剂（a实现小号） - （小号）-3,3'-双（（小号）-2-（羟甲基）吡咯烷-1-羰基）-9， 9'-二甲基-9- ħ，9' ħ - [1,1'- bipyrido [3,4 b ]吲哚2-氧化物。有趣的是，（A混合物小号） - （小号）-3,3'-双（（小号）-2-（羟甲基）吡咯烷-1-羰基）-9,9'-二甲基-9- ħ，9' ħ-[1,1'-联吡啶[3,4- b ]吲哚] 2-氧化物和（a R）-（S）-3,3'-bis（（S）-2-（羟甲基）吡咯烷-1-羰基）-9,9'-二甲基-9- ħ，9' ħ - [1,1'- bipyrido [3,4 b ]吲哚2-氧化物也能够提供高对映体选择性高达95％也就是相同使用纯的（一个小号）