(E)-N-(4-phenylbut-3-en-2-ylidene)aniline | 17424-79-2

• 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: (E)-N-(4-phenylbut-3-en-2-ylidene)aniline
• 英文别名: 2-methyl-1,4-diphenyl-1-aza-1,3-butadiene；2-methyl-1,4-diphenyl-1-azabuta-1,3-diene；N-(4-phenylbut-3-en-2-ylidene)aniline；4-Phenyl-3-buten-2-one N-phenylimine；4-Phenyl-but-3-en-2-on-phenylimin；Benzalaceton-anil；4-phenyl-3-buten-2-one-N-phenylimine；N,4-diphenylbut-3-en-2-imine
• CAS: 17424-79-2
• 化学式: C₁₆H₁₅N
• 分子量: 221.302
• InChiKey: SWZIFMPZYZSWMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  正丁基锂 、 (E)-N-(4-phenylbut-3-en-2-ylidene)aniline 在 lithium bromide 、 氯化铵 作用下， 以 2-甲基四氢呋喃 、 正己烷 、 水 为溶剂， 反应 2.0h， 以97%的产率得到N-(3-methyl-1-phenylhept-1-en-3-yl)aniline
  参考文献：
  名称：

  Highly regioselective control of 1,2-addition of organolithiums to α,β-unsaturated compounds promoted by lithium bromide in 2-methyltetrahydrofuran: a facile and eco-friendly access to allylic alcohols and amines

  摘要：

  Very high regioselective 1,2-addition of organolithiums to alpha,beta-unsaturated carbonyl-like compounds (ketones, aldehydes, and imines) in the presence of LiBr was achieved by carrying out reactions in the sustainable solvent 2-methyltetrahydrofuran. Excellent yields (in isolated product) of allylic alcohols and allylic amines were recovered under a simple experimental procedure at 0 degrees C. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.067
• 作为产物：
  描述：

  苯胺 、 苄叉丙酮 以 甲苯 为溶剂， 生成 (E)-N-(4-phenylbut-3-en-2-ylidene)aniline
  参考文献：
  名称：

  通过将胺加成α，β-不饱和醛和酮来理解α，β-不饱和亚胺的形成：分析和理论研究

  摘要：

  结合使用原位红外光谱（ReactIR）和DFT计算来了解哪些因素决定了将伯胺添加到α，β-不饱和醛和酮中的选择性，即1,2-对1,4-添加。已经发现，在大多数系统中，1,2-加成产物（加成和消除后的α，β-不饱和亚胺）通常占主导地位。但是，诸如甲基乙烯基酮之类的例外情况会选择性地产生1,4-加成产物。这已通过DFT计算得到了合理化，该计算表明涉及主要构象效应，主要受羰基取代基的空间效应控制，从而形成了一种模型，该模型提供了简单，可预测的α，β-不饱和亚胺制备方法，可用于原位合成。

  DOI：

  10.1021/jo5007366

文献信息

• “On-Water,” Microwave-Assisted, Pd-Catalyzed Synthesis of Indoles from Imines and o-Difunctionalized Arenes
  作者：José Barluenga、Agustín Jiménez-Aquino、Fernando Aznar、Carlos Valdés

  DOI：10.1002/chem.201000753

  日期：——

  Regioselectively substituted indoles are prepared by a Pd‐catalyzed CC/CN bond‐forming sequence from imines and o‐dihaloarenes or o‐haloarene sulfonates. The heterogeneous reaction as a suspension in water and under microwave heating offers important advantages in comparison with the conventional reaction in an organic solvent, among them, operational simplicity, the employment of KOH solutions instead

  区域选择性取代的吲哚通过Pd催化的C中制备 C / C  N键形成序列从亚胺和ö -dihaloarenes或ö -haloarene磺酸盐。与在有机溶剂中的常规反应相比，在水中和微波加热下作为悬浮液的非均相反应具有重要的优势，其中包括操作简便，使用KOH溶液代替醇盐以及显着减少反应时间。
• Halogenated ketenes. 38. Cycloaddition of .alpha.,.beta.-unsaturated imines with ketenes to yield both .beta.- and .delta.-lactams
  作者：William T. Brady、C. H. Shieh

  DOI：10.1021/jo00163a014

  日期：1983.7
• Influence of Phosphoramidites in Copper-Catalyzed Conjugate Borylation Reaction
  作者：Cristina Sole、Amadeu Bonet、André H. M. de Vries、Johannes G. de Vries、Laurent Lefort、Henrik Gulyás、Elena Fernández

  DOI：10.1021/om300194k

  日期：2012.11.26

  Copper(I) has become the preferred metal to catalyze the beta-boration of alpha,beta-unsaturated carbonyl compounds, and now we demonstrate that easily accessible monodentate chiral ligands, such as phosphoramidites and phosphites, can be convenient alternative ligands to induce asymmetry in the enantioselective version of this reaction, particularly in the beta-boration of alpha,beta-unsaturated imines.
• Reactions of Zirconocene–1-Aza-1,3-diene Complexes with Acyl Cyanides: Substrate-Dependent Synthesis of Acyl- or Non-Acyl-Substituted Pyrroles
  作者：Meijun Xiong、Shasha Yu、Xin Xie、Shi Li、Yuanhong Liu

  DOI：10.1021/acs.organomet.5b00801

  日期：2015.12.14

  Insertion of acyl cyanides into azazirconacydopentenes derived from 1,3-azadienes has been described, which affords acyl- or non-acyl-substituted pyrroles upon acidic quenching. These reactions are initialized through C=O insertion into the azazirconacycle to afford seven-membered oxaazazirconacycles. In the cases of 1,4- or 1,2,4-substituted azadienes, addition of a second molecule of acyl cyanide followed by cyclization upon acidic quenching leads to acyl-substituted pyrroles. In the cases of 1,3,4-substituted azadienes, the addition of a second molecule of acyl cyanide cannot proceed due to the steric hindrance caused by the R-3 group on the zirconium intermediate. Acidic quenching of the resulting zirconium intermediate affords non-acyl-substituted pyrroles.
• Ackland, Mark J.; Danks, Timothy N.; Howells, Mark E., Journal of the Chemical Society. Perkin transactions I, 1998, # 4, p. 813 - 817
  作者：Ackland, Mark J.、Danks, Timothy N.、Howells, Mark E.

  DOI：——

  日期：——