2-(4-hydroxyphenyl)-2-(piperidin-1-yl)acetonitrile | 486-30-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(4-hydroxyphenyl)-2-(piperidin-1-yl)acetonitrile
• 英文别名: girgensohnine；Girgensonine；2-(4-hydroxyphenyl)-2-piperidin-1-ylacetonitrile
• CAS: 486-30-6
• 化学式: C₁₃H₁₆N₂O
• mdl: MFCD00612486
• 分子量: 216.283
• InChiKey: HNFAREZIVBKEJQ-UHFFFAOYSA-N

物化性质

• 熔点：
  147-148 °C(Solv: methanol (67-56-1))
• 沸点：
  350.8±32.0 °C(Predicted)
• 密度：
  1.169±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  47.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-hydroxyphenyl)-2-(piperidin-1-yl)acetonitrile 、 3-phenylpropyl-magnesium bromide 在 乙醚 作用下， 生成 4-(4-苯基-1-哌啶子基-丁基)-苯酚
  参考文献：
  名称：

  DE1011427

  摘要：

  公开号：
• 作为产物：
  描述：

  哌啶 、 对羟基苯甲醛 、 丙酮氰醇 在 sulfuric acid supported on silica gel 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以73%的产率得到2-(4-hydroxyphenyl)-2-(piperidin-1-yl)acetonitrile
  参考文献：
  名称：

  Design, synthesis, acetylcholinesterase inhibition and larvicidal activity of girgensohnine analogs on Aedes aegypti, vector of dengue fever

  摘要：

  Girgensohnine alkaloid was used as a natural model in the design and generation of new alkaloid-like alpha-aminonitrile series that was completed by the use of SSA-catalyzed Strecker reaction between commercial and inexpensive substituted benzaldehydes, piperidine (pyrrolidine, morpholine and N-methylpiperazine) and acetone cyanohydrin. Calculated ADMETox parameters of the designed analogs revealed their good pharmacokinetic profiles indicating lipophilic characteristics. In vitro AChE enzyme test showed that obtained alpha-aminonitriles could be considered as AChEIs with micromolar IC50 values ranging from 42.0 to 478.0 mu M (10.3-124.0 mu g/mL). Among this series, the best AChE inhibitor was the Pyrrolidine alpha-aminonitrile 3 (IC50 = 42 mu M) followed by the piperidine alpha-aminonitriles 2 and 6 (IC50 = 45 mu M and IC50 = 51 mu M, respectively), and the compound 7 (IC50 = 51 mu M). In vivo insecticidal activity of more active AChEIs against Aedes aegypti larvae was also performed showing a good larvicidal activity at concentrations less than 140 ppm, highlighting products 2 and 7 that could serve as lead compounds to develop new potent and selective insecticides. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.067

文献信息

• A carbon dioxide-promoted three-component Strecker reaction
  作者：Ruslan V. Fauziev、Roman E. Ivanov、Ilya V. Kuchurov、Sergei G. Zlotin

  DOI：10.1039/d1gc03161a

  日期：——

  but also as a reaction promoter via in situ formation of carbonic acid which provides a gradual release of the true cyanating agent (HCN) from available KCN. The reaction conditions (pressure, temperature, and concentrations of reagents) were optimized, and various aromatic and aliphatic amines and aldehydes were transformed into valuable α-amino nitriles including prospective pharmacological substances

  醛、胺和 KCN 的三组分 Strecker 反应首次在超临界二氧化碳中进行。在提议的程序中，无毒和不可燃的二氧化碳不仅作为一种环境友好的反应介质，而且作为反应促进剂通过原位碳酸的形成使真正的氰化剂 (HCN) 从可用的 KCN 中逐渐释放出来。优化反应条件（压力、温度和试剂浓度），将各种芳香族和脂肪族胺和醛转化为有价值的α-氨基腈，包括预期的药理物质。使用等摩尔量的氰试剂，在“绿色”溶剂介质中在温和条件（90 bar，35°C）下在密封高压釜中进行该过程以及产品的高产率和所开发程序的可扩展性使其成为适用于可持续的工业应用。
• Two Zn(II)/Cd(II) Coordination Polymers as Recyclable Heterogeneous Catalysts for an Efficient Room-Temperature Synthesis of α-Aminonitriles via the Solvent-Free Strecker Reaction
  作者：Sheeba Khan、Datta Markad、Sanjay K. Mandal

  DOI：10.1021/acs.inorgchem.2c03369

  日期：2023.1.9

  versatile building blocks in the synthesis of natural or artificial amino acids as well as important intermediates in organic synthesis. For their synthesis, the three-component Strecker reaction involving an aldehyde or a ketone together with amines and trimethylsilyl cyanide is used. In the literature, hydrothermally produced metal-based heterogeneous Lewis acid catalysts have been utilized in various

  α-氨基腈是合成天然或人工氨基酸的多功能组成部分，也是有机合成中的重要中间体。对于它们的合成，使用涉及醛或酮与胺和三甲基甲硅烷基氰化物的三组分 Strecker 反应。在文献中，水热法生产的金属基多相路易斯酸催化剂已在各种溶剂中使用。在这项工作中，我们旨在通过 (a) 制作两种具有 d 10金属中心的预催化剂 [Zn(hipamifba)(H 2 O)]·2H 2 O} n ( 1 ) 和 [ Cd(hipamifba)(H 2 O) 2 ]·2H 2 O}n ( 2 )（其中 H 2 hipamifba = 4-(((4-((羧甲基)氨基甲酰基)苯基)氨基)甲基)苯甲酸），通过简单且可扩展的室温方法，以及 (b) 展示用途这些配位聚合物 (CP) 作为非常有效、可回收和多相的催化剂，用于 Strecker 反应，在环境条件下无溶剂反应下以高产率形成 α-氨基腈。这也使我们能够通过活化
• Diphenylethylamines. I. The Preparation of Tertiary Amines by the Grignard Reaction^1,2
  作者：Louis H. Goodson、Hope Christopher

  DOI：10.1021/ja01157a097

  日期：1950.1
• Juraschewskii; Stepanowa, Zhurnal Obshchei Khimii, 1946, vol. 16, p. 141,144
  作者：Juraschewskii、Stepanowa

  DOI：——

  日期：——