N-(3-methoxyphenyl)-1,1-diphenylmethanimine | 255897-33-7

• 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-(3-methoxyphenyl)-1,1-diphenylmethanimine
• 英文别名: N-(Diphenylmethylene)-3-methoxyaniline
• CAS: 255897-33-7
• 化学式: C₂₀H₁₇NO
• 分子量: 287.361
• InChiKey: OPEKOSPLTWAVJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(3-methoxyphenyl)-1,1-diphenylmethanimine 在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 间氨基苯甲醚
  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：

  N-(3-甲氧基苯基)甲酰胺 在 四(三苯基膦)钯 、 三乙胺 、 三氯氧磷 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 6.0h， 生成 N-(3-methoxyphenyl)-1,1-diphenylmethanimine
  参考文献：
  名称：

  Palladium-Catalyzed Diarylation of Isocyanides with Tetraarylleads for the Selective Synthesis of Imines and α-Diimines

  摘要：

  Using tetraaryllead compounds (PbAr4) as arylating reagents, isocyanides undergo selective diarylation in the presence of palladium catalysts such as Pd(OAc)(2) or Pd(PPh3)(4) to afford imines and/or alpha-diimines based on the isocyanide employed. With aliphatic isocyanides, imines are obtained preferentially, whereas alpha-diimines are formed in the case of electron-rich aromatic isocyanides. The differences in imine/alpha-diimine selectivity can be attributed to the stability of imidoylpalladium intermediates formed in this catalytic reaction. Compared with other arylating reagents, tetraaryllead compounds are excellent candidates for use in the selective transformations to imines and/or alpha-diimines, especially in terms of inhibiting the oligomerization of isocyanides, which results in a lower product selectivity in many transition-metal-catalyzed reactions of isocyanides.

  DOI：

  10.1021/acs.joc.9b01639

文献信息

• Copper‐Catalysed Electrophilic Amination of Aryl(alkenyl) Boronic Acids with Nitrogen‐Containing Hypervalent Iodine (III) Reagent
  作者：Yuanyuan Hu、Songlin Zheng、Wu Fan、Weiming Yuan

  DOI：10.1002/adsc.202100594

  日期：2021.10.19

  A copper-catalysed electrophilic N-imination of aryl(alkenyl) boronic acids with a stable hypervalent iodine(III) reagent containing a transferable (diarylmethylene)amino group is developed. The electrophilic C−N cross-coupling reaction proceeds smoothly at room temperature under oxidant-free and base-free conditions, which is further characterized by the broad functional group compatibility, thereof

  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。
• Arylamine synthesis
  申请人：Massachusetts Institute of Technology

  公开号：US06323366B1

  公开（公告）日：2001-11-27

  The present invention provides a method for the preparation of a wide range of primary arylamines. The arylamines are prepared in two efficient, straightforward transformations: 1) an activated aryl group and an imine group are combined, in the presence of a transition metal catalyst, under conditions wherein the transition metal catalyst catalyzes the formation of a carbon-nitrogen bond between the activated carbon of the arene and the imine nitrogen; and 2) the resulting N-aryl imine is transformed, via any of a number of standard protocols, to the primary arylamine. The method of the invention may also be exploited in the preparation of vinylamines.

  本发明提供了一种制备广泛范围的主要芳胺的方法。这些芳胺是通过两种高效、直接的转化制备的：1）在过渡金属催化剂的存在下，将活化的芳基和亚胺基结合在一起，在过渡金属催化剂催化的条件下，在芳烃的活化碳和亚胺氮之间催化形成碳-氮键；2）通过任何一种标准方案将产生的N-芳基亚胺转化为主要芳胺。该发明的方法还可用于制备乙烯胺。
• Visible-light induced cross-electrophile coupling of imines and anhydrides to synthesize α-amino ketones
  作者：Renxu Cao、Yu Liu、Xiaoxin Shi、Jun Zheng

  DOI：10.1039/d3cc03028h

  日期：——

  cross-electrophile coupling of readily available imines and anhydrides was developed. Under mild reaction conditions, the umpolung reactivity of diverse imines engaged with anhydrides gives a variety of α-amino ketones with good yields and a broad functional group compatibility. Primary mechanistic studies revealed that this transformation might proceed through a radical–radical cross coupling pathway dominantly

  α-氨基酮是合成和药物化学中的重要基序。然而，从可行的前体中直接获取这些基序的有效方法是有限的。在此，开发了一种可见光介导的易得亚胺和酸酐的还原交叉亲电子偶联。在温和的反应条件下，多种亚胺与酸酐的反极性反应可得到多种α-氨基酮，具有良好的收率和广泛的官能团相容性。主要机制研究表明，这种转变可能主要通过自由基-自由基交叉耦合途径进行。
• Highly Reactive, General, and Long-Lived Catalysts for Coupling Heteroaryl and Aryl Chlorides with Primary Nitrogen Nucleophiles
  作者：Qilong Shen、Shashank Shekhar、James P. Stambuli、John F. Hartwig

  DOI：10.1002/anie.200462629

  日期：2005.2.18
• IMPROVED ARYLAMINE SYNTHESIS
  申请人：MASSACHUSETTS INSTITUTE OF TECHNOLOGY

  公开号：EP1100774B1

  公开（公告）日：2004-01-21