3-phenyl-3-(phenylamino)propanenitrile | 33328-81-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-phenyl-3-(phenylamino)propanenitrile
• 英文别名: 3-Anilino-3-phenyl-propionitrile；3-anilino-3-phenylpropanenitrile
• CAS: 33328-81-3
• 化学式: C₁₅H₁₄N₂
• 分子量: 222.29
• InChiKey: FQLLWGBWTGYKQS-UHFFFAOYSA-N

物化性质

• 熔点：
  80-82 °C
• 沸点：
  416.2±33.0 °C(Predicted)
• 密度：
  1.129±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  4
• 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

• 作为产物：
  描述：

  苯胺 在 2,2,6,6-四甲基哌啶氧化物 、 四丁基高氯酸铵 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 17.25h， 生成 3-phenyl-3-(phenylamino)propanenitrile
  参考文献：
  名称：

  电化学自由基-自由基交叉偶联：从未活化的亚胺和烷基腈中直接获得 β-氨基腈

  摘要：

  在本文中，首次描述了通过电化学自由基-自由基交叉偶联从未活化的亚胺和烷基腈中直接获得 β-氨基腈。使用丰富且廉价的烷基腈，无需预官能化，用于亚胺的还原性氰基烷基化，使反应原子和步骤经济。该合成策略为构建β-氨基腈衍生物提供了一种绿色、温和、高效的方法。

  DOI：

  10.1039/d2gc00457g

文献信息

• Reactions of Schiff Bases with Superoxide Ion in Acetonitrile
  作者：Katsuyoshi Shibata、Yoshiyuki Saito、Katsuyoshi Urano、Masaki Matsui

  DOI：10.1246/bcsj.59.3323

  日期：1986.10

  The reactions of Schiff bases such as N-benzylideneanilines with superoxide ion in acetonitrile under mild conditions gave the cyanomethyl adducts, 3-arylamino-3-arylpropionitriles, as the main products in relatively good yields. In the case of N-(4-nitrobenzylidene)aniline, the adduct was further oxidized to β-anilino-4-nitrocinnamonitrile. No oxidative products such as amides were obtained except

  席夫碱（如 N-亚苄基苯胺）与乙腈中的超氧离子在温和条件下反应得到氰甲基加合物，3-芳基氨基-3-芳基丙腈，作为主要产物，产率相对较好。在 N-（4-硝基亚苄基）苯胺的情况下，加合物被进一步氧化为 β-苯胺基-4-硝基肉桂腈。除了N-(4-氯-和4-硝基亚苄基)苯胺的反应外，没有得到氧化产物如酰胺。
• Cyanomethylation of imines enabled by a mild deprotonation of acetonitrile using a combination of TMSCF3 and CsF
  作者：Jie Tong、Jiaheng Li、Juncheng Li、Savia L. Boyer、Ting Wang

  DOI：10.1016/j.tetlet.2024.154937

  日期：2024.5

  biology. Herein we reported a method to synthesize -amino nitriles, the crucial synthetic precursor to -amino acids. By using a nucleophilic base-complex, generated from TMSCF and CsF, addition of acetonitrile to a series of aromatic imines offered the corresponding -amino nitriles in excellent yields. Moreover, other electron withdrawing group bearing methyl group could be deprotonated to produce a good

  -氨基酸是化学和生物学中的重要结构单元。在此，我们报道了一种合成β-氨基腈的方法，β-氨基腈是β-氨基酸的重要合成前体。通过使用由 TMSCF 和 CsF 生成的亲核碱配合物，将乙腈加成到一系列芳香族亚胺中，以优异的产率提供相应的氨基腈。此外，在这种温和的条件下，其他带有甲基的吸电子基团可以去质子化以产生良好的亲核试剂。
• Product-Catalyzed Addition of Alkyl Nitriles to Unactivated Imines Promoted by Sodium Aryloxide/Ethyl(trimethylsilyl)acetate (ETSA) Combination
  作者：Thomas Poisson、Vincent Gembus、Sylvain Oudeyer、Francis Marsais、Vincent Levacher

  DOI：10.1021/jo802763b

  日期：2009.5.1

  The first transition-metal-free addition of alkyl nitriles to unactivated irnines was developed using a catalytic combination of 4-MeOC6H4CNa and TMSCH2CO2Et to promote the reaction. The corresponding beta-amino nitriles are obtained in good to almost quantitative isolated yields under mild conditions. A mechanism involving an autocatalytic pathway is proposed on the basis of experimental observations.
• Elektrokatalytische Cyanomethylierung von Azomethinen: Eine neue Synthese f�r ?-Aminonitrile
  作者：U. Hess、A.-K. Raasch、M. Schulze

  DOI：10.1002/prac.19923340607

  日期：——

  Certain Schiff-bases (2 - 7) react in acetonitrile (1) at a Hg-cathode in a new electrocatalyzed cyanomethylation method in good yields without side-products to beta-aminonitriles (2a - 7a). The synthesis is initiated by an electrochemical deprotonation of 1 by azomethine-radical anions in catalytical amount to acetonitril anions (B-). During nucleophilic reaction of B- with 2 - 7 up to its complete consumption, the cyanomethylation synthon B- is regenerated in a cyclic, self-reproducing process. Quantum chemical calculation in context with cyanomethylation product analysis permit mechanistical insights and exact prediction of suitable azomethines and coupling position for B-.
• Tin-Mediated Addition of Bromoaceto-Nitrile to Aldimines
  作者：Peipei Sun、Yongmin Zhang

  DOI：10.1080/00397919708004176

  日期：1997.9

  In the presence of tin powder, the addition of bromoacetonitrile to aldimines gives beta-amino nitriles in THF. Chlorotrimethylsilane can accelerate the reaction.