1-(4-chlorophenylamino)cyclohexanecarbonitrile | 19970-13-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-(4-chlorophenylamino)cyclohexanecarbonitrile
• 英文别名: 1-<4-Chlor-anilino>-cyclohexan-carbonsaeure-(1)-nitril；1-(4-Chloroanilino)cyclohexanecarbonitrile；1-(4-chloroanilino)cyclohexane-1-carbonitrile
• CAS: 19970-13-9
• 化学式: C₁₃H₁₅ClN₂
• 分子量: 234.728
• InChiKey: AMVBMGORRGNMSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  1-(4-chlorophenylamino)cyclohexanecarbonitrile 在 次氯酸叔丁酯 作用下， 以 苯 为溶剂， 生成 1--cyclohexancarbonsaeure-(1)-nitril
  参考文献：
  名称：

  Pinchuk,A.M. et al., Journal of general chemistry of the USSR, 1968, vol. 38, # 5, p. 969 - 974

  摘要：

  DOI：
• 作为产物：
  描述：

  1-苯胺环己烷甲腈 、 以 苯 为溶剂， 生成 1-(4-chlorophenylamino)cyclohexanecarbonitrile
  参考文献：
  名称：

  Pinchuk,A.M. et al., Journal of general chemistry of the USSR, 1968, vol. 38, # 5, p. 969 - 974

  摘要：

  DOI：

文献信息

• Nanostructured oxytyramine catalyst for the facile one-pot synthesis of cyclohexanecarbonitrile derivatives
  作者：Priya Arora、Jaspreet Kaur Rajput、Harminder Singh

  DOI：10.1039/c5ra20150k

  日期：——

  still a less explored subject, and our investigation provides an insight into the efficient synthesis of cyclohexanecarbonitrile derivatives using a ketone i.e. cyclohexanone. When compared with other catalytic systems reported in the literature, ours showed superior catalytic activity at a remarkably low catalyst loading i.e. 5 mg.

  本报告开发了可循环利用的磁性多相有机催化剂OT @ Si @ SPION，目的是合成环己烷腈。所制备的纳米催化剂已通过多种技术进行了全面表征，并且其催化活性已在一个一锅反应中进行了测试，该反应涉及从环己酮和胺中原位形成亚胺，然后进一步与TMSCN进行亲核加成。此外，尽管此的Strecker反应是百年的历史，它适用于酮类仍然少探索对象，和我们的调查提供一种使用洞察环己烷衍生物的有效合成的酮，即环己酮。与文献中报道的其他催化体系相比，我们的催化剂在极低的催化剂负载（即5 mg）下表现出优异的催化活性。
• Fe₃ O₄ /MIL-101(Fe) nanocomposite as an efficient and recyclable catalyst for Strecker reaction
  作者：Mohammad Mahdi Mostafavi、Farnaz Movahedi

  DOI：10.1002/aoc.4217

  日期：2018.4

  FT‐IR, SEM, TEM, BET, and VSM. This hybrid magnetic nanocomposite was employed as heterogeneous catalyst for α‐amino nitriles synthesis through three‐component condensation reaction of aldehydes (ketones), amines, and trimethylsilyl cyanide in EtOH, at room temperature. The recoverability and reusability was admitted for the heterogeneous magnetic catalyst; no significant reduction of catalytic activity

  在氨基修饰的Fe 3 O 4 @SiO 2纳米粒子存在下，通过溶剂热法制备了高度多孔的金属有机骨架MIL-101（Fe），以实现Fe 3 O 4 / MIL-101（ Fe）纳米复合材料，其特征在于XRD，FT-IR，SEM，TEM，BET和VSM。这种杂化磁性纳米复合材料在室温下通过醛（酮），胺和三甲基甲硅烷基氰化物在EtOH中的三组分缩合反应，被用作α-氨基腈合成的非均相催化剂。均相磁性催化剂具有良好的可回收性和可重复使用性。即使在五个连续的反应循环后也未观察到催化活性的显着降低。
• Gallic acid-functionalized magnetic nanoparticles: a convenient and green approach for synthesis of α-aminonitriles under solvent-free conditions
  作者：Esmaiel Eidi、Mohamad Z. Kassaee、Zahra Nasresfahani、Peter T. Cummings

  DOI：10.1007/s11164-018-3603-x

  日期：2019.2

  acid-coated magnetic nanoparticles were efficiently prepared, characterized by Fourier transform infrared spectroscopy, X-ray diffraction, vibrating sample magnetometry, scanning electron microscopy, and transmission electron microscopy, and employed as an environmentally friendly and recyclable catalyst for one-pot synthesis of three-component reaction via Strecker reaction, incorporating aldehydes/ketones

  摘要 高效制备了没食子酸包覆的磁性纳米粒子，并通过傅里叶变换红外光谱，X射线衍射，振动样品磁强度法，扫描电子显微镜和透射电子显微镜进行了表征，并被用作一种环境友好的可回收催化剂，用于一锅合成通过无溶剂条件下的醛/酮，胺和三甲基甲硅烷基氰化物通过Strecker反应进行三组分反应。操作简便，产物纯度，天然资源和催化剂的可重复使用性被认为是该方案的明显特征，有望将其发展成为一种廉价，高效且清洁的合成α-氨基腈的策略。 图形概要
• Synthesis of α-aminonitriles under mild catalytic, metal-free conditions
  作者：Baskar Nammalwar、Chelsea Fortenberry、Richard A. Bunce

  DOI：10.1016/j.tetlet.2013.11.035

  日期：2014.1

  alpha-Aminonitriles have been synthesized by a Strecker synthesis from aldehydes and ketones under mild catalytic, metal-free conditions. Aromatic aldehydes (1 equiv) were reacted with TMSCN (1 equiv) and aromatic and 1 degrees or 2 degrees aliphatic amines (1 equiv) in EtOH containing 3 mol % of NH4Cl to give high yields of alpha-aminonitriles. An alternative to adding NH4Cl as a catalyst involved the use of excess TMSCN (1.2 equiv) to promote the process. The reaction was also successful under microwave conditions using excess TMSCN with no solvent. Ketones similarly reacted with aromatic amines and excess TMSCN under conventional and microwave heating, but 30 mol % of added NH4Cl was required for optimum conversion. (C) 2013 Elsevier Ltd. All rights reserved.
• Sulfamic acid-functionalized magnetic Fe3O4 nanoparticles as an efficient and reusable catalyst for one-pot synthesis of α-amino nitriles in water
  作者：M.Z. Kassaee、Hassan Masrouri、Farnaz Movahedi

  DOI：10.1016/j.apcata.2011.01.018

  日期：2011.3

  Grafting of chlorosulfuric acid on the amino-functionalized Fe3O4 nanoparticles afforded sulfamic acid-functionalized magnetic Fe3O4 nanoparticles (SA-MNPs) as a novel organic-inorganic hybrid heterogeneous catalyst, which was characterized by XRD, FT-IR, TGA, TEM, and elemental analysis. The catalytic activity of SA-MNPs was probed through one-pot synthesis of a-amino nitrites via three-component couplings of aldehydes (or ketones), amines and trimethylsityl cyanide in water, at room temperature. The heterogeneous catalyst could be recovered easily and reused many times without significant loss of its catalytic activity. (c) 2011 Elsevier B.V. All rights reserved.