2-(o-toluidino)-2-phenylacetonitrile | 15190-66-6

• 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: 2-(o-toluidino)-2-phenylacetonitrile
• 英文别名: 2-phenyl-2-(o-tolylamino)acetonitrile；2-(2-Methylanilino)-2-phenylacetonitrile
• CAS: 15190-66-6
• 化学式: C₁₅H₁₄N₂
• 分子量: 222.29
• InChiKey: JMXVLPCHVQMGSN-UHFFFAOYSA-N

物化性质

• 熔点：
  72-73 °C
• 沸点：
  383.5±30.0 °C(Predicted)
• 密度：
  1.131±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  35.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(o-toluidino)-2-phenylacetonitrile 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 14.0h， 生成 E-[2-nitro-1-phenyl-vinyl]-o-methyl-phenyl amine
  参考文献：
  名称：

  Diarylimidoylcyanides, an Attractive Class of Intermediate: Novel Synthesis of α‐Anilino‐β‐Nitroenamines, N, N′‐ Disubstituted Amidines and Substituted Phenyl Glyoxate

  摘要：

  DOI：

  10.1080/00397910500446902
• 作为产物：
  描述：

  扁桃腈 、 邻甲苯胺 在 乙醇 作用下， 生成 2-(o-toluidino)-2-phenylacetonitrile
  参考文献：
  名称：

  Sachs, Chemische Berichte, 1901, vol. 34, p. 503

  摘要：

  DOI：

文献信息

• (Bromodimethyl)sulfonium Bromide Catalyzed One-Pot Synthesis of α-Aminonitriles
  作者：Biswanath Das、R. Ramu、B. Ravikanth、K. Reddy

  DOI：10.1055/s-2006-926421

  日期：2006.5

  A novel, simple and efficient one-pot synthesis of α-aminonitriles has been achieved by a three-component condensation of carbonyl compounds, amines and trimethylsilyl cyanide in the presence of (bromodimethyl)sulfonium bromide as a catalyst at room temperature. The products were obtained in high yields and in short reaction times.

  在室温下，在（溴二甲基）溴化锍作为催化剂的存在下，羰基化合物、胺和三甲基甲硅烷基氰化物的三组分缩合实现了一种新颖、简单、高效的一锅法合成α-氨基腈。产物以高产率和短反应时间获得。
• K2PdCl4 catalyzed efficient multicomponent synthesis of α-aminonitriles in aqueous media
  作者：Bikash Karmakar、Julie Banerji

  DOI：10.1016/j.tetlet.2010.03.059

  日期：2010.5

  An efficient, mild and environmentally friendly method has been developed for the Strecker reaction to synthesize α-aminonitriles in the presence of K2PdCl4 as a catalyst. The three-component one-pot condensation of an aldehyde, amine and trimethylsilyl cyanide proceeded smoothly in water to afford the corresponding product in high yield with short reaction times.

  已经开发出一种有效，温和且环保的方法，用于在存在K 2 PdCl 4作为催化剂的情况下进行Strecker反应以合成α-氨基腈。醛，胺和三甲基甲硅烷基氰化物的三组分一锅缩合在水中平稳进行，以高收率和短反应时间提供相应的产物。
• Boric Acid Catalysed Synthesis of α-Aminonitriles by a Three-Component Reaction at Room Temperature
  作者：Zahed Karimi-Jaberi、Abdolaziz Bahrani

  DOI：10.3184/174751912x13352842814921

  日期：2012.6

  A simple, efficient, and cost-effective method has been developed for the one-pot, three-component condensation reaction of trimethylsilyl cyanide, aldehydes and aromatic amines using boric acid as a heterogeneous solid acid catalyst, under solvent-free conditions. α-Aminonitriles were synthesised relatively quickly in good yields at room temperature.

  开发了一种简单、高效且经济的方法，用于在无溶剂条件下使用硼酸作为非均相固体酸催化剂进行三甲基氰化硅烷、醛和芳香胺的一锅三组分缩合反应。α-氨基腈在室温下以良好的收率相对较快地合成。
• Convenient and rapid synthesis of α-aminonitriles starting directly from nitro compounds in water
  作者：Biswanath Das、Gandham Satyalakshmi、Kanaparthy Suneel

  DOI：10.1016/j.tetlet.2009.03.150

  日期：2009.6

  A distinct approach for the synthesis of α-aminonitriles has been discovered by three-component reaction of nitroarenes, aldehydes, and TMSCN using indium in dilute aqueous HCl at room temperature. The products were formed in high yields (86–96%) within a short period of time (5–20 min). This one-pot conversion consists of the following steps: (i) reduction of nitro compounds to amines, (ii) formation

  在室温下，使用稀盐酸水溶液中的铟，通过硝基芳烃，醛和TMSCN的三组分反应，发现了一种独特的合成α-氨基腈的方法。产品在短时间内（5-20​​分钟）以高收率（86-96％）形成。这种一锅转化包括以下步骤：（i）将硝基化合物还原为胺，（ii）由胺和醛形成亚胺，以及（iii）将氰化物阴离子加到亚胺上。
• A unique combination of KI/ZnFe₂O₄as a catalyst for oxidative Strecker reaction
  作者：Leila Ghandi、Maryam Kazemi Miraki、Meghdad Karimi、Iman Radfar、Akbar Heydari

  DOI：10.1002/aoc.4616

  日期：2019.1

  α‐Aminonitriles as key intermediates for the preparation of α‐amino acid derivatives, amides, diamines, peptides, proteins and heterocycles were synthesized through methylarene oxidation in the Strecker reaction using a unique combination of KI/ZnFe2O4 as the best catalyst and aqueous tert‐butyl hydroperoxide as oxidant. A wide range of amines and methylarenes were converted to the corresponding products

  α-氨基腈是制备α-氨基酸衍生物，酰胺，二胺，肽，蛋白质和杂环的关键中间体，是在Strecker反应中通过甲基芳烃氧化合成的，采用独特的KI / ZnFe 2 O 4作为最佳催化剂，叔丁基过氧化氢水溶液作氧化剂。多种胺和甲基芳烃被转化为相应的产物。操作简便，反应时间短和催化剂的可回收性是该方案的优势。