2-(Benzylamino)-2-(4-nitrophenyl)acetonitrile | 1067616-34-5

• 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-(Benzylamino)-2-(4-nitrophenyl)acetonitrile
• CAS: 1067616-34-5
• 化学式: C₁₅H₁₃N₃O₂
• 分子量: 267.287
• InChiKey: VFVHMWVOGQTZRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 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：
  81.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对硝基苯甲醛 、 苄胺 在 3C₁₂H₆N₂O₄^(2-)*2Tb⁽³⁺⁾*2C₃H₇NO 、 magnesium sulfate 作用下， 以 氘代氯仿 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 2-(Benzylamino)-2-(4-nitrophenyl)acetonitrile
  参考文献：
  名称：

  Lanthanide coordination polymer constructed from 2,2′-bipyridyl-4,4′-dicarboxylic acid: Structure, catalysis and fluorescence

  摘要：

  Two new isostructural lanthanide coordination polymers (Ln-CPs) [Ln(2)(bpdc)(3)(DMF)(2)] (Ln = Tb for 1, Eu for 2) with two kinds of one-dimensional channels along the a axis, were synthesized by 2,2 '-bipyridyl-4,4 '-dicarboxylic acid (H(2)bpdc) under solvothermal conditions. With exposed Lewis acid Ln(3+) centers, 1 as a heterogeneous catalyst shows good catalytic reactivity and selectivity for the Strecker reaction affording medium to excellent conversion yields. Luminescent studies illustrate that 1 and 2 show intensive green and red luminescence triggered by efficient antenna effect of ligands under UV light, respectively. Moreover, 1 exhibits sensitive fluorescent response to Cu2+ in DMF solution. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2015.08.012

文献信息

• Catalyst-Free Strecker Reaction in Water: A Simple and Efficient Protocol Using Acetone Cyanohydrin as Cyanide Source
  作者：Paola Galletti、Matteo Pori、Daria Giacomini

  DOI：10.1002/ejoc.201100089

  日期：2011.7

  nitriles through a one-pot, three-component Strecker reaction of a carbonyl compound, amine, and acetone cyanohydrin in water has been developed. Reactions proceed very efficiently without any catalyst at room temperature with high chemoselectivity and give, in some cases, the expected α-amino nitrile pure after direct separation from water. The protocol is particularly efficient for both aliphatic and

  开发了一种简单、方便、实用的方法，通过羰基化合物、胺和丙酮氰醇在水中的一锅三组分 Strecker 反应合成 α-氨基腈。反应在室温下在没有任何催化剂的情况下非常有效地进行，具有高化学选择性，在某些情况下，直接与水分离后得到预期的纯α-氨基腈。该方案对于脂肪族和芳香族醛以及环酮以及伯胺和仲胺都特别有效。报道了 Strecker 反应对 1,2-二胺获得 1,2-二氨基腈和环状仲胺的不寻常应用。
• Highly efficient and convenient Strecker reaction of carbonyl compounds and amines with TMSCN catalyzed by MCM-41 anchored sulfonic acid as a recoverable catalyst
  作者：Mohammad G. Dekamin、Zahra Mokhtari

  DOI：10.1016/j.tet.2011.10.087

  日期：2012.1

  sulfonic acid (MCM-41–SO3H) was found to be a highly efficient and recoverable heterogeneous catalyst for the three-component Strecker reaction of aldehydes or ketones and diverse amines using trimethylsilyl cyanide (TMSCN) to afford the corresponding α-amino nitriles under mild conditions in high to quantitative yields. The simple experimental procedure along with easy recovery and reusability of the

  发现MCM-41锚固磺酸（MCM-41–SO 3 H）是一种高效且可回收的多相催化剂，可利用三甲基甲硅烷基氰化物（TMSCN）进行醛或酮与多种胺的三组分Strecker反应。 α-氨基腈在温和条件下以高产率到定量产率。简单的实验程序以及催化剂的易于回收和可重复使用性已导致开发出一种清洁且环境友好的合成α-氨基腈的方法。
• One-pot three-component synthesis of α-amino nitriles catalyzed by nano powder TiO2 P 25
  作者：Seyed Meysam Baghbanian、Maryam Farhang、Robabeh Baharfar

  DOI：10.1016/j.cclet.2010.12.003

  日期：2011.5

  A simple and efficient method has been developed for the synthesis of α-amino nitriles from aldehydes, amines and trimethylsilyl cyanide (Me3SiCN) in the presence of a catalytic amount of cyanuric acid at room temperature.

  已开发出一种简单有效的方法，在室温下在催化量的氰尿酸存在下，由醛，胺和三甲基甲硅烷基氰化物（Me3SiCN）合成α-氨基腈。
• Synthesis of Highly Porous Mn2O3-Doped Fe3O4 NPs with a Dual Catalytic Function Using Asymmetric Water Soluble Mn-Salen Complex as a Reducing Agent and Template: Catalytic Activity over One-Pot Strecker Synthesis from Alcohols in Recyclable TAIm[CN] Ionic Liquid
  作者：Eman Khalaf、Ameer A. Alameri、Jitendra Malviya、T. CH. Anil Kumar、Farag M. A. Altalbawy、Raed H. C. Alfilh、Milad Kazemnejadi

  DOI：10.1007/s10562-022-04210-0

  日期：——

  the Strecker synthesis from primary and secondary alcohols under mild conditions. TAIm[CN] ionic liquid (IL) was used as an efficient solvent and nitrile-required reagent to synthesis of α-aminonitriles. TAIm[CN] IL could be recycled for several times by a simple recovery and subsequent treatment. Also, the catalytic activity of the NPs was evaluated toward the selective alcohol oxidation to carbonyl

  利用不对称Mn/TEMPO-Salen络合物作为还原剂和模板原位合成Mn/TEMPO掺杂的Fe 3 O 4纳米粒子。Mn/TEMPO 掺杂的 Fe 3 O 4 NPs 作为前驱体的后续热分解提供了高度多孔 (641 m 2 g –1 ) Mn 2 O 3掺杂的 Fe 3 O 4NP。通过 FTIR、BET、TGA、VSM、ICP、TEM、XRD、UV-Vis 和 XPS 分析对高多孔纳米粒子进行了表征。在温和条件下，通过伯醇和仲醇的 Strecker 合成法合成 α-氨基腈时，发现纳米粒子具有高稳定性和催化活性。TAIm[CN]离子液体（IL）被用作合成α-氨基腈的有效溶剂和腈所需试剂。通过简单的回收和后续处理，TAIm[CN]IL可以多次循环利用。此外，还评估了纳米粒子对选择性醇氧化为羰基化合物以及从醇和芳基胺直接转化亚胺的催化活性。Mn 2 O 3掺杂的Fe 3 O 4纳米粒子可以回收
• Magnetic Solid Sulfonic Acid Decorated with Hydrophobic Regulators: A Combinatorial and Magnetically Separable Catalyst for the Synthesis of α-Aminonitriles
  作者：Akbar Mobaraki、Barahman Movassagh、Babak Karimi

  DOI：10.1021/co500022g

  日期：2014.7.14

  A three-component, Strecker reaction of a series of aldehydes or ketones, amines, and trimethylsilyl cyanide for the synthesis of alpha-aminonitriles in the presence of a catalytic amount of a magnetic solid sulfonic acid catalyst, Fe3O4@SiO2@Me&Et-PhSO3H under solvent-free conditions have been investigated. This catalyst, with a combination of hydrophobicity and acidity on the Fe3O4@SiO2 core-shell of the magnetic nanobeads, as well as its water-resistant property, enabled easy mass transfer and catalytic activity in the Strecker reaction. The catalyst was easily separated by an external magnet and the recovered catalyst was reused in 6 successive reaction cycles without any significant loss of activity.