2-(N-anilino)-2-(n-pentyl)acetonitrile

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(N-anilino)-2-(n-pentyl)acetonitrile
• 英文别名: 2-Anilinoheptanenitrile
• 化学式: C₁₃H₁₈N₂
• 分子量: 202.299
• InChiKey: CGHJQOIJPOWKAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• 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

• 作为产物：
  描述：

  三甲基氰硅烷 、 正己醛 、 苯胺 在 cerium(III) chloride 作用下， 以 乙腈 为溶剂， 反应 1.25h， 以93%的产率得到2-(N-anilino)-2-(n-pentyl)acetonitrile
  参考文献：
  名称：

  氯化铈 (III)：一种用于合成 α-氨基腈的高效试剂

  摘要：

  摘要 我们报道了在 MeCN 中羰基化合物、胺和 TMSCN 的高效、单锅、三组分缩合反应；在环境温度下，催化量的氯化铈 (III) 显着促进了反应，产率极好，对其他取代基没有任何不利影响。该方法为合成 α-氨基腈提供了一种优雅的替代方法。反应快速、清洁，所得产品纯度高。

  DOI：

  10.1080/00397910701578180

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。
• 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。
• Cerium(III) Chloride: A Highly Efficient Reagent for the Synthesis of α‐Aminonitriles
  作者：M. A. Pasha、H. M. Nanjundaswamy、V. P. Jayashankara

  DOI：10.1080/00397910701578180

  日期：2007.11

  report a highly efficient, one‐pot, three‐component condensation of carbonyl compounds, amines, and TMSCN in MeCN; the reaction is significantly promoted by the catalytic amount of cerium(III) chloride at ambient temperature in excellent yields without any adverse effect on the other substituents. The method afforded an elegant alternative to the synthesis of α‐aminonitriles. The reactions are fast and

  摘要 我们报道了在 MeCN 中羰基化合物、胺和 TMSCN 的高效、单锅、三组分缩合反应；在环境温度下，催化量的氯化铈 (III) 显着促进了反应，产率极好，对其他取代基没有任何不利影响。该方法为合成 α-氨基腈提供了一种优雅的替代方法。反应快速、清洁，所得产品纯度高。
• Tin exchanged zeolite as catalyst for direct synthesis of α-amino nitriles under solvent-free conditions
  作者：Arpan K. Shah、Noor-ul H. Khan、Govind Sethia、S. Saravanan、Rukhsana I. Kureshy、Sayed H.R. Abdi、Hari C. Bajaj

  DOI：10.1016/j.apcata.2012.01.001

  日期：2012.3

  Sn exchanged HBeta zeolite was prepared and characterized by PXRD, surface area, TPD and TEM analysis. The Sn exchanged zeolite was found to be highly efficient catalyst for the direct synthesis of alpha-amino nitrite from various ketones and aldehydes with amine and trimethyl silylcyanide (TMSCN) under solvent-free condition. Excellent yield of alpha-amino nitrile (up to 96%) was achieved within 10-120 min at room temperature. The Sn exchanged HBeta zeolite was recovered and reused several times without the loss of its catalytic performance. (C) 2012 Elsevier B.V. All rights reserved.
• Pamar, M. Geeta; Govender; Pillay, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 1, p. 110 - 116
  作者：Pamar, M. Geeta、Govender、Pillay、Abrahamse、Nanjundaswamy

  DOI：——

  日期：——