methyl threo-(2-phenyl-2-(N-methoxycarbonyl-2'-piperidyl)acetate | 258825-18-2

• 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: methyl threo-(2-phenyl-2-(N-methoxycarbonyl-2'-piperidyl)acetate
• 英文别名: methyl (2R,2'R)-2-phenyl-2-(N-methoxycarbonyl-2'-piperidyl)acetate；methyl (2R)-2-[(1R)-2-methoxy-2-oxo-1-phenylethyl]piperidine-1-carboxylate
• CAS: 258825-18-2
• 化学式: C₁₆H₂₁NO₄
• 分子量: 291.347
• InChiKey: YFZVEGFTSMWCML-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl threo-(2-phenyl-2-(N-methoxycarbonyl-2'-piperidyl)acetate 在 碘代三甲硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 哌醋右甲酯
  参考文献：
  名称：

  从N-甲氧基羰基哌啶合成对映体富集的哌醋甲酯的简便方法。

  摘要：

  [公式：见正文]该报告介绍了一种从哌啶开始制备旋光哌醋甲酯的新方法。该方法包括通过利用电化学氧化将N-甲氧基羰基哌啶转化为相应的α-甲氧基化氨基甲酸酯I，然后与旋光的Evans酰亚胺II偶联反应，以生产具有高立体选择性苏氨酸-（2R，2可以通过三步轻松地从III制备R'-哌醋甲酯（IV； Ar = Ph；利他林）。

  DOI：

  10.1021/ol9905046
• 作为产物：
  描述：

  重氮甲烷 、 2-(1-Methoxycarbonylpiperidin-2-yl)-2-phenylacetic acid 以 乙醚 为溶剂， 生成 methyl erythro-(2-phenyl-2-(N-methoxycarbonyl-2'-piperidyl)acetate 、 methyl threo-(2-phenyl-2-(N-methoxycarbonyl-2'-piperidyl)acetate
  参考文献：
  名称：

  A Convenient Method for Synthesis of Optically Active Methylphenidate from N-Methoxycarbonylpiperidine by Utilizing Electrochemical Oxidation and Evans Aldol-type Reaction

  摘要：

  A new method to prepare optically active methylphenidate starting from piperidine is described. The method consists of a transformation of N-methoxycarbonylated piperidine to the corresponding alpha-methoxylated carbamate utilizing electrochemical oxidation followed by the coupling reaction with optically active Evans imides to produce optically active methylphenidate derivatives with high stereoselectivity (erythrolthreo=5.3/94.7, the three isomer; 99.6%ee). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00653-0

文献信息

• A Convenient Method for Synthesis of Optically Active Methylphenidate from N-Methoxycarbonylpiperidine by Utilizing Electrochemical Oxidation and Evans Aldol-type Reaction
  作者：Yoshihiro Matsumura、Yasuhisa Kanda、Kimihiro Shirai、Osamu Onomura、Toshihide Maki

  DOI：10.1016/s0040-4020(00)00653-0

  日期：2000.9

  A new method to prepare optically active methylphenidate starting from piperidine is described. The method consists of a transformation of N-methoxycarbonylated piperidine to the corresponding alpha-methoxylated carbamate utilizing electrochemical oxidation followed by the coupling reaction with optically active Evans imides to produce optically active methylphenidate derivatives with high stereoselectivity (erythrolthreo=5.3/94.7, the three isomer; 99.6%ee). (C) 2000 Elsevier Science Ltd. All rights reserved.
• A Convenient Method for Synthesis of Enantiomerically Enriched Methylphenidate from <i>N</i>-Methoxycarbonylpiperidine
  作者：Yoshihiro Matsumura、Yasuhisa Kanda、Kimihiro Shirai、Osamu Onomura、Toshihide Maki

  DOI：10.1021/ol9905046

  日期：1999.7.1

  [formula: see text] This report describes a new method to prepare optically active methylphenidate starting from piperidine. The method consists of a transformation of N-methoxycarbonylpiperidine to the corresponding alpha-methoxylated carbamate I by utilizing electrochemical oxidation followed by the coupling reaction with optically active Evans imides II to produce optically active methylphenidate

  [公式：见正文]该报告介绍了一种从哌啶开始制备旋光哌醋甲酯的新方法。该方法包括通过利用电化学氧化将N-甲氧基羰基哌啶转化为相应的α-甲氧基化氨基甲酸酯I，然后与旋光的Evans酰亚胺II偶联反应，以生产具有高立体选择性苏氨酸-（2R，2可以通过三步轻松地从III制备R'-哌醋甲酯（IV； Ar = Ph；利他林）。