(E)-N-(1,3-diphenylallyl)aniline

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-N-(1,3-diphenylallyl)aniline
• 英文别名: N-[(E)-1,3-diphenylprop-2-enyl]aniline
• 化学式: C₂₁H₁₉N
• 分子量: 285.389
• InChiKey: DAHUWCZJJVQONR-WUKNDPDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-N-(1,3-diphenylallyl)aniline 在 disodium ethylenediaminetetraacetic acid 、 碳酸氢钠 、 Oxone 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 生成 (E)-N-[(E)-1,3-diphenylallylidene]aniline oxide 、 (Z)-N-((E)-1,3-diphenylallylidene)aniline oxide
  参考文献：
  名称：

  A modular approach to α,β-unsaturated N-aryl ketonitrones

  摘要：

  A modular approach to alpha,beta-unsaturated N-aryl ketonitrones has been developed. Specifically, condensation of anilines and enals followed by alkylation of the resulting alpha,beta-unsaturated imines provided N-allyl anilines, which were subjected to oxidation with Oxone (R) to form alpha,beta-unsaturated N-aryl ketonitrones. This modular approach is general and provides rapid access to diversely substituted alpha,beta-unsaturated N-aryl ketonitrones with a single purification step in good yields. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.06.083
• 作为产物：
  描述：

  反式肉桂醛 在 magnesium sulfate 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 2.0h， 生成 (E)-N-(1,3-diphenylallyl)aniline
  参考文献：
  名称：

  电子和空间控制有机锂试剂与烯醛胺的区域选择性加成反应。

  摘要：

  衍生自萘-1-甲醛和无环α，β-不饱和醛的亚胺与有机锂试剂的反应方式取决于亚胺氮原子上取代基的特征。在氮原子上具有吸电子芳基的亚胺表现为朝向有机锂试剂的1,2-亚胺。相反，带有烷基或庞大的芳基的亚胺有利于有机锂试剂的1，4-加成。基于分子轨道计算，合理化了亚胺氮原子上取代基的电子和空间反应模式调节。

  DOI：

  10.1021/jo015766b

文献信息

• Electronic and Steric Control in Regioselective Addition Reactions of Organolithium Reagents with Enaldimines
  作者：Kiyoshi Tomioka、Yoshito Shioya、Yasuo Nagaoka、Ken-ichi Yamada

  DOI：10.1021/jo015766b

  日期：2001.10.1

  A reaction mode of imines derived from naphthalene-1-carbaldehyde and acyclic alpha,beta-unsaturated aldehydes with organolitium reagents was dependent on the characteristic nature of a substituent on the imine nitrogen atom. An imine having an electron-withdrawing aryl group on the nitrogen atom behaves as a 1,2-directing imine toward organolithium reagents. In contrast, an imine bearing an alkyl

  衍生自萘-1-甲醛和无环α，β-不饱和醛的亚胺与有机锂试剂的反应方式取决于亚胺氮原子上取代基的特征。在氮原子上具有吸电子芳基的亚胺表现为朝向有机锂试剂的1,2-亚胺。相反，带有烷基或庞大的芳基的亚胺有利于有机锂试剂的1，4-加成。基于分子轨道计算，合理化了亚胺氮原子上取代基的电子和空间反应模式调节。
• Metal-free synthesis of allylic amines by cross-dehydrogenative-coupling of 1,3-diarylpropenes with anilines and amides under mild conditions
  作者：Zhiming Wang、Hanjie Mo、Dongping Cheng、Weiliang Bao

  DOI：10.1039/c2ob06826e

  日期：——

  Dehydrogenative cross-coupling reaction of primary anilines, secondary anilines, carboxamides, and sulfonamides with 1,3-diarylpropenes to form a series of allylic amines promoted by DDQ have been realized. Both monoallylation and diallylation products can be selectively synthesized when primary anilines are used as the starting materials. The method may provide a wide scope of allylamines in scientific research including biologically active compound library construction.

  已实现由DDQ促进的脱氢交叉偶联反应，涉及一级苯胺、二级苯胺、羧酰胺和磺酰胺与1,3-二芳基丙烯的反应，生成一系列烯丙基胺。当以一级苯胺为起始物时，可选择性合成单烯丙基化和双烯丙基化产物。该方法可能在科学研究中提供广泛的烯丙基胺，包括生物活性化合物库的建设。
• Anion‐Dependent Imidazolium‐Based Catalysts for Allylation of Aniline with Tunable Regioselectivity
  作者：María Albert‐Soriano、Isidro M. Pastor

  DOI：10.1002/adsc.202000102

  日期：2020.6.15

  Metal‐free catalysts based on 1,3‐bis(carboxymethyl)imidazolium halides mediate the reaction between allylic alcohols and anilines, providing the corresponding N ‐, 2‐ and 4‐allylaniline isomers selectively. The imidazolium counterion plays a crucial role in the outcome of the reaction. Thus, while the imidazolium chloride selectively provides the N ‐substituted aniline, the bromide and iodide imidazolium

  基于1,3-双（羧甲基）咪唑鎓卤化物的无金属催化剂介导烯丙醇与苯胺之间的反应，选择性地提供相应的N-，2-和4-烯丙胺异构体。咪唑鎓抗衡离子在反应结果中起关键作用。因此，尽管咪唑氯化物选择性地提供了N溴代苯胺和碘代咪唑鎓盐是经取代的苯胺，分别产生2和4烯丙​​基苯胺异构体，具有极好的选择性。本文介绍了一组可通过简单调节获得的互补催化剂，以进行苯胺的高度区域选择性烯丙基化反应。不仅催化剂以简单，易于扩展的方式合成，而且由于与反应物之间的良好相互作用，因此可以在无溶剂的反应条件下进行回收利用。
• Amidation of 1,3-Diarylallylic Compounds Catalysed by 2,3-Dichloro-5,6-Dicyano-1,4-Benzoquinone with Molecular Oxygen as the Terminal Oxidant
  作者：Dongping Cheng、Xiayi Zhou、Kun Yuan、Jizhong Yan

  DOI：10.3184/174751916x14537221307662

  日期：2016.3

  An efficient amidation has been developed of 1,3-diarylpropenes by carboxamides, sulfonamides, carbamates and anilines catalysed by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and benzoyl peroxide with molecular oxygen. The corresponding products were obtained in moderate to good yields.

  在 2,3-二氯-5,6-二氰基-1,4-苯醌和过氧化苯甲酰与分子氧的催化下，甲酰胺、磺酰胺、氨基甲酸酯和苯胺对 1,3-二芳基丙烯进行了有效的酰胺化。以中等至良好的收率获得了相应的产物。
• Rational Optimization of Lewis-Acid Catalysts for Direct Alcohol Amination, Part 2 - Titanium Triflimide as New Active Catalyst
  作者：Pierre-Adrien Payard、Céline Finidori、Laurélia Guichard、Damien Cartigny、Matthieu Corbet、Lhoussain Khrouz、Laurent Bonneviot、Raphael Wischert、Laurence Grimaud、Marc Pera-Titus

  DOI：10.1002/ejoc.202000413

  日期：2020.6.16

  reactivity of a new, previously undescribed (see part I), titanium triflimide catalyst was further investigated for the direct amination of alcohols. Addition of pyridine‐based ligands allows to increase the activity. The scope of the reaction has been significantly increased compared to other Lewis‐acid‐based protocols. Finally, some mechanistic insights based on EPR spectroscopy and DFT are provided.

  进一步研究了一种新的，以前未描述的（见第一部分）三氟化钛催化剂的反应性，用于直接胺化醇。添加吡啶基配体可以增加活性。与其他基于路易斯酸的方案相比，该反应的范围已大大增加。最后，提供了一些基于EPR光谱和DFT的力学见解。