2-(4-chlorophenyl)-2-((4-methoxyphenyl)amino)propanenitrile | 67474-26-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(4-chlorophenyl)-2-((4-methoxyphenyl)amino)propanenitrile
• 英文别名: 2-(4-Chlorophenyl)-2-(4-methoxyanilino)propanenitrile
• CAS: 67474-26-4
• 化学式: C₁₆H₁₅ClN₂O
• 分子量: 286.761
• InChiKey: SFLWBPOMJOZVOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  45
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  甲氧苯胺 、 2-amino-2-(4-chlorophenyl)propanenitrile 在 titanium(IV) isopropylate 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以59%的产率得到2-(4-chlorophenyl)-2-((4-methoxyphenyl)amino)propanenitrile
  参考文献：
  名称：

  氰基借：钛与胺的氰醇直接胺化和对映选择性实例。

  摘要：

  开发了通过催化氰基借位反应将氰醇与胺直接胺化的方法。该转化具有广泛的底物范围，出色的官能团相容性以及非常温和和简单的操作。此外，由奎宁和（S）-BINOL配体负载的钛催化剂能够实现不对称的氰基-借位反应，具有中等至高的对映选择性。

  DOI：

  10.1039/c9cc08576a

文献信息

• From Zn(II)-Carboxylate to Double-Walled Zn(II)-Carboxylato Phosphate MOF: Change in the Framework Topology, Capture and Conversion of CO₂, and Catalysis of Strecker Reaction
  作者：Mayank Gupta、Dinesh De、Kapil Tomar、Parimal K. Bharadwaj

  DOI：10.1021/acs.inorgchem.7b02443

  日期：2017.12.4

  Interestingly, this adsorbed CO2 could be converted very efficiently to cyclic carbonates under mild conditions using 2′ as the catalyst in the presence of tetrabutylammonium bromide as the cocatalyst. The presence of open metal sites in 2′ makes it an efficient heterogeneous catalyst for solvent-free three-component Strecker reaction using various aldehydes/ketones together with amines and trimethylsilyl

  配体H 2 L是通过将咪唑部分连接至间苯二甲酸的5-位而建立的。它形成两种类型的多孔骨架，[Zn（L）]·2DMF·2H 2 O} n（1）和[（CH 3）2 NH 2 ] [Zn 2（L）（H 2 O）PO 4 ]·2DMF} n（2）。1是多孔的中性骨架，具有rtl金红石3,6-conn拓扑，而2是具有双壁六角形通道的有机金属磷酸盐阴离子多孔骨架。骨架1'（去溶剂化）表现出中等的CO 2吸附（在273 K，1 bar下为58 cc g –1），而2'（去溶剂化）显示出对CO 2的高吸附（111.7 cc g –1或22 ）的微孔性质。wt％在273 K，1巴下）。有趣的是，在溴化四丁铵作为助催化剂的情况下，使用2'作为催化剂，在温和的条件下，该吸附的CO 2可以非常有效地转化为环状碳酸酯。2'中存在开放金属位点使其在室温下以高收率使用多种醛/酮以及胺和三甲基甲硅烷基氰化物进行无溶剂
• Brønsted acid-catalyzed efficient Strecker reaction of ketones, amines and trimethylsilyl cyanide
  作者：Guang-Wu Zhang、Dong-Hua Zheng、Jing Nie、Teng Wang、Jun-An Ma

  DOI：10.1039/b924272d

  日期：——

  A general method for the one-pot, three-component Strecker reaction of ketones was developed using Brønsted acids as organocatalysts. A series of α-aminonitriles were obtained in good to excellent yields (79–99%). A preliminary extension to a catalytic enantioselective three-component Strecker reaction of ketones (up to 40% ee) is also described.

  使用布朗斯台德酸作为有机催化剂，开发了一种用于酮的一锅，三组分斯特雷克反应的通用方法。获得了一系列α-氨基腈，收率良好至优异（79–99％）。还描述了酮的催化对映选择性三组分Strecker反应的初步扩展（最高40％ee）。
• Solvent-free three component Strecker reaction of ketones using highly recyclable and hydrophobic sulfonic acid based nanoreactors
  作者：Babak Karimi、Daryoush Zareyee

  DOI：10.1039/b911388f

  日期：——

  An efficient and environmentally benign system was developed for the one-pot three-component Strecker reaction of ketones under solvent-free conditions, with the use of a highly recoverable SBA-15 supported sulfonic acid. Also findings concerning the effects of functionalized inert groups and silica backbone pore size on substrate scope, catalytic activity and recycling behavior of the catalysts were briefly discussed. The simple experimental and product isolation procedure accompanied by easy recovery and reusability of the catalyst could be considered as attractive features of this new protocol which will hopefully develop a clean strategy for the synthesis of α-amino nitriles.

  通过使用高回收率的 SBA-15 支承磺酸，开发出了一种高效且对环境无害的系统，用于在无溶剂条件下进行酮类化合物的一锅三组分 Strecker 反应。此外，还简要讨论了官能化惰性基团和二氧化硅骨架孔径对底物范围、催化活性和催化剂回收行为的影响。实验和产物分离过程简单，催化剂易于回收和重复使用，这些都是这一新方案的诱人之处，有望为 α-氨基腈的合成开发出一种清洁的策略。
• 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.
• Cyano-borrowing: titanium-catalyzed direct amination of cyanohydrins with amines and enantioselective examples
  作者：Tang-Lin Liu、Zhao-Feng Li、Jing Tao、Qing-Hua Li、Wan-Fang Li、Qian Li、Li-Qing Ren、Yun-Gui Peng

  DOI：10.1039/c9cc08576a

  日期：——

  The direct amination of cyanohydrins with amines via a catalytic cyano-borrowing reaction was developed. The transformation features broad substrate scope, excellent functional group compatibility, and very mild and simple operations. Moreover, a titanium catalyst supported by quinine and (S)-BINOL ligands enabled an asymmetric cyano-borrowing reaction with moderate to high enantioselectivity.

  开发了通过催化氰基借位反应将氰醇与胺直接胺化的方法。该转化具有广泛的底物范围，出色的官能团相容性以及非常温和和简单的操作。此外，由奎宁和（S）-BINOL配体负载的钛催化剂能够实现不对称的氰基-借位反应，具有中等至高的对映选择性。