2-(naphthalen-2-yl)-2-(phenylamino)propanenitrile

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(naphthalen-2-yl)-2-(phenylamino)propanenitrile
• 英文别名: 2-Anilino-2-naphthalen-2-ylpropanenitrile
• 化学式: C₁₉H₁₆N₂
• 分子量: 272.349
• InChiKey: QGTMQKQTBIPUFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  35.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  三甲基氰硅烷 、 苯胺 、 2-萘乙酮 在 C(C₆H₄C₃N₂H₃(CH₃))4⁽⁴⁺⁾*4I^(1-)=C(C₆H₄C₃N₂H₃(CH₃))4I₄ 、 palladium diacetate 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以86%的产率得到2-(naphthalen-2-yl)-2-(phenylamino)propanenitrile
  参考文献：
  名称：

  含双（N-杂环碳）-钯物种的有机金属空心球：在三组分Strecker反应中的催化应用

  摘要：

  空心球催化剂是通过在四咪唑结构单元和乙酸钯之间的3D网络形成而制备的。在空心球生长过程中同时形成的双（N-杂环卡宾）-钯物种在酮的一锅三组分Strecker反应中表现出出色的作为非均相催化剂的活性（参见图片； TMS =三甲基甲硅烷基）。

  DOI：

  10.1002/anie.201003101

文献信息

• Efficient Three-Component Strecker Reaction of Aldehydes/Ketones via NHC-Amidate Palladium(II) Complex Catalysis
  作者：Jamie Jarusiewicz、Yvonne Choe、Kyung Soo Yoo、Chan Pil Park、Kyung Woon Jung

  DOI：10.1021/jo900163w

  日期：2009.4.3

  A simple and efficient one-pot, three-component method has been developed for the synthesis of α-aminonitriles. This Strecker reaction is applicable for aldehydes and ketones with aliphatic or aromatic amines and trimethylsilyl cyanide in the presence of a palladium Lewis acid catalyst in dichloromethane solvent at room temperature.

  开发了一种简单高效的一锅三组分合成α-氨基腈的方法。这种 Strecker 反应适用于醛和酮与脂肪族或芳香族胺和三甲基氰化硅烷，在钯路易斯酸催化剂的存在下，在二氯甲烷溶剂中，室温。
• N-HETEROCYCLIC CARBENE-AMIDO PALLADIUM(II) CATALYSTS AND METHOD OF USE THEREOF
  申请人：Jung Kyung Woon

  公开号：US20100036131A1

  公开（公告）日：2010-02-11

  A new N-heterocyclic catalyst system which contains N-heterocyclic carbene and amido as ligands, which are strongly bound to a palladium metal. Another heteroatom functionality can be used as a third ligand L. The NHC-amidate ligand system is unique in structure, and shows excellent reactivities in a number of chemical reactions. The chemical reactions include carbon-carbon and carbon-heteroatom (oxygen and nitrogen) bond formations, and oxidation reactions of saturated carbon chemicals via C—H activation.

  一个新的N-杂环催化剂系统包含N-杂环卡宾和酰胺作为配体，它们与钯金属结合紧密。另一个杂原子功能基可以用作第三个配体L。NHC-酰胺配体系统在结构上独特，并在许多化学反应中显示出优异的反应性。这些化学反应包括碳-碳和碳-杂原子（氧和氮）键的形成，以及通过C—H活化对饱和碳化学物质的氧化反应。
• Organometallic Hollow Spheres Bearing Bis(N-Heterocyclic Carbene)-Palladium Species: Catalytic Application in Three-Component Strecker Reactions
  作者：Jaewon Choi、Hye Yun Yang、Hae Jin Kim、Seung Uk Son

  DOI：10.1002/anie.201003101

  日期：2010.10.11

  Hollow‐sphere catalysts were prepared by means of 3D network formation between a tetraimidazolium building block and palladium acetate. The bis(N‐heterocyclic carbene)–palladium species that were concomitantly formed during growth of the hollow spheres showed excellent activity as heterogeneous catalysts in one‐pot three‐component Strecker reactions of ketones (see picture; TMS=trimethylsilyl).

  空心球催化剂是通过在四咪唑结构单元和乙酸钯之间的3D网络形成而制备的。在空心球生长过程中同时形成的双（N-杂环卡宾）-钯物种在酮的一锅三组分Strecker反应中表现出出色的作为非均相催化剂的活性（参见图片； TMS =三甲基甲硅烷基）。
• Fe(Cp)2PF6 catalyzed efficient Strecker reactions of ketones and aldehydes under solvent-free conditions
  作者：Noor-ul H. Khan、Santosh Agrawal、Rukhsana I. Kureshy、Sayed H.R. Abdi、Surendra Singh、Eringathodi Suresh、Raksh V. Jasra

  DOI：10.1016/j.tetlet.2007.11.136

  日期：2008.1

  The synthesis of alpha-aminonitriles of ketones and aldehydes was performed in very short reaction times (20 min) with excellent yields in the presence of 5 mol % of Fe(Cp)(2)PF6 under solvent-free conditions. (c) 2007 Published by Elsevier Ltd.
• Sulfated tungstate: a green catalyst for Strecker reaction
  作者：Sagar P. Pathare、Krishnacharya G. Akamanchi

  DOI：10.1016/j.tetlet.2011.12.027

  日期：2012.2

  A straightforward, mild, efficient, and general method has been developed for the synthesis of alpha-aminonitriles via Strecker reaction starting from aldehydes or ketones, amines, and trimethylsilyl cyanide in the presence of sulfated tungstate as a heterogeneous mild solid acid catalyst at room temperature and solvent free condition. The developed method has been successfully applied for the synthesis of a wide range of alpha-aminonitriles with variable functionality. (C) 2011 Elsevier Ltd. All rights reserved.