1-methyl-6-oxo-2-phenylpiperidine-3-carboxamide

• 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: 1-methyl-6-oxo-2-phenylpiperidine-3-carboxamide
• 英文别名: (2S,3S)-1-methyl-6-oxo-2-phenylpiperidine-3-carboxamide
• 化学式: C₁₃H₁₆N₂O₂
• 分子量: 232.282
• InChiKey: AAPYFDAXQGYUCK-CMPLNLGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  63.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-methyl-6-oxo-2-phenylpiperidine-3-carboxamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以75%的产率得到[(2R,3S)-1-Methyl-2-phenylpiperidin-3-yl]methanamine
  参考文献：
  名称：

  Toward Lead-Oriented Synthesis: One-Pot Version of Castagnoli Condensation with Nonactivated Alicyclic Anhydrides

  摘要：

  One-pot variation of Castagnoli condensation, that is, reaction of cyclic anhydrides, amines, and aldehydes, has been developed as a combinatorial approach to 1,2-disubstituted 5-oxopyrrolidine- and 6-oxopiperidine-3-carboxylic acids, as well as their benzo-analogues. Utility of the method to multigram preparation of building blocks and synthetic intermediates was also demonstrated. The final products are obtained in high yields and diastereoselectivity. The method fits well in the concept of lead-oriented synthesis; in particular, it can be used for the design of lead-like Compound libraries, even if the strictest cut-offs are applied to the physicochemical properties of their members.

  DOI：

  10.1021/co4001277
• 作为产物：
  描述：

  苯亚甲基甲胺 在 N,N'-羰基二咪唑 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 N,N-二甲基甲酰胺 为溶剂， 反应 55.0h， 生成 1-methyl-6-oxo-2-phenylpiperidine-3-carboxamide
  参考文献：
  名称：

  Toward Lead-Oriented Synthesis: One-Pot Version of Castagnoli Condensation with Nonactivated Alicyclic Anhydrides

  摘要：

  One-pot variation of Castagnoli condensation, that is, reaction of cyclic anhydrides, amines, and aldehydes, has been developed as a combinatorial approach to 1,2-disubstituted 5-oxopyrrolidine- and 6-oxopiperidine-3-carboxylic acids, as well as their benzo-analogues. Utility of the method to multigram preparation of building blocks and synthetic intermediates was also demonstrated. The final products are obtained in high yields and diastereoselectivity. The method fits well in the concept of lead-oriented synthesis; in particular, it can be used for the design of lead-like Compound libraries, even if the strictest cut-offs are applied to the physicochemical properties of their members.

  DOI：

  10.1021/co4001277

文献信息

• Toward Lead-Oriented Synthesis: One-Pot Version of Castagnoli Condensation with Nonactivated Alicyclic Anhydrides
  作者：Sergey V. Ryabukhin、Dmitriy M. Panov、Dmitry S. Granat、Eugeniy N. Ostapchuk、Dmitriy V. Kryvoruchko、Oleksandr O. Grygorenko

  DOI：10.1021/co4001277

  日期：2014.3.10

  One-pot variation of Castagnoli condensation, that is, reaction of cyclic anhydrides, amines, and aldehydes, has been developed as a combinatorial approach to 1,2-disubstituted 5-oxopyrrolidine- and 6-oxopiperidine-3-carboxylic acids, as well as their benzo-analogues. Utility of the method to multigram preparation of building blocks and synthetic intermediates was also demonstrated. The final products are obtained in high yields and diastereoselectivity. The method fits well in the concept of lead-oriented synthesis; in particular, it can be used for the design of lead-like Compound libraries, even if the strictest cut-offs are applied to the physicochemical properties of their members.