5-phenylpiperidine-3-carboxamide | 10131-80-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 5-phenylpiperidine-3-carboxamide
• 英文别名: 5-phenyl-piperidine-3-carboxylic acid amide；5-Phenyl-nipecotinamid；5-Phenylpiperidine-3-carboxamide
• CAS: 10131-80-3
• 化学式: C₁₂H₁₆N₂O
• mdl: MFCD18073138
• 分子量: 204.272
• InChiKey: FLBLONKUAGMTEW-UHFFFAOYSA-N

物化性质

• 沸点：
  420.4±45.0 °C(Predicted)
• 密度：
  1.103±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-phenylpiperidine-3-carboxamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 cis-(5-phenylpiperidin-3-yl)-methylamine
  参考文献：
  名称：

  Fast and Efficient Access to a Family of Multifunctional 1,3,5-Trisubstituted Piperidines

  摘要：

  A collection of new 1,3,5-trisubstituted piperidines has been synthesized starting from the commercially available 5-bromonicotinic acid. A unified, diastereoselective strategy allows the controlled access to both cis and trans stereochemistries. The heterocyclic compounds thus prepared bear multiple functional groups suitable for structural diversification and combichem protocols.

  DOI：

  10.1080/00397910701877608

文献信息

• Modulation of Pharmacologically Relevant Properties of Piperidine Derivatives by Functional Groups in an Equatorial or Axial β‐Position to the Amino Group
  作者：Patrick Schnider、Cosimo Dolente、Henri Stalder、Rainer E. Martin、Viktoria Reinmüller、Roman Marty、Caroline Wyss Gramberg、Björn Wagner、Holger Fischer、André M. Alker、Klaus Müller

  DOI：10.1002/cbic.201900474

  日期：2020.1.15

  property-based design of bioactive compounds. Impacts on amine basicity are very pronounced for the β-equatorial functional groups and parallel basicity-lowering effects known for acyclic amine derivatives. For β-axial functional groups, the basicity-lowering effects are generally decreased, with the nitrile group as the only exception. Basicity and lipophilicity modulations observed for β-axial functional

  合成了13个5个取代的N-哌啶基-3-苯基哌啶衍生物的差向异构对，以探索碱性，亲脂性，水溶性和膜渗透性（通过与胺单元成直角的赤道或轴向位置）的立体定向调节。尽管此综合数据集可增强对影响碱性和亲脂性的多种因素的洞察力，但它填补了重要的知识空白，为基于特性的生物活性化合物设计提供了参考框架。β-赤道官能团对胺碱性的影响非常显着，无环胺衍生物已知降低平行碱度的作用。对于β轴官能团，降低碱度的作用通常会降低，其中腈基是唯一的例外。就分子内氢键，偶极相互作用和特殊的溶剂化作用而言，针对β轴官能团观察到的碱度和亲脂性调节非常多样且合理化。参照亲脂性讨论了水溶性和（人工）膜渗透性。
• Fast and Efficient Access to a Family of Multifunctional 1,3,5-Trisubstituted Piperidines
  作者：José Luis Díaz、Dolors Fernández-Forner、Jordi Bach、Rodolfo Lavilla

  DOI：10.1080/00397910701877608

  日期：2008.8.19

  A collection of new 1,3,5-trisubstituted piperidines has been synthesized starting from the commercially available 5-bromonicotinic acid. A unified, diastereoselective strategy allows the controlled access to both cis and trans stereochemistries. The heterocyclic compounds thus prepared bear multiple functional groups suitable for structural diversification and combichem protocols.