(2S,3S)-piperidine-2,3-dicarboxylic acid 3-methyl ester | 163254-44-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,3S)-piperidine-2,3-dicarboxylic acid 3-methyl ester
• 英文别名: (2S,3S)-3-methoxycarbonylpiperidine-2-carboxylic acid
• CAS: 163254-44-2
• 化学式: C₈H₁₃NO₄
• 分子量: 187.196
• InChiKey: MYTFJOFIAANGMS-WDSKDSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3S)-piperidine-2,3-dicarboxylic acid 3-methyl ester 在 盐酸 作用下， 反应 4.0h， 以93%的产率得到(2S,3S)-piperidine-2,3-dicarboxylic acid hydrochloride
  参考文献：
  名称：

  Neuromediator类似物：由（2 S）-2-苯基甘氨醇合成顺式（2 R，3 S）和反式（2 S，3 S）-2,3-哌啶二羧酸

  摘要：

  从相同的手性引发剂：2-苯基甘氨醇以对映纯形式获得2，3-哌啶二羧酸的顺式和反式异构体。该合成主要基于经由Stille的氮杂-环化/氢化程序的δ-内酰胺形成，该程序在此包括不对称诱导。

  DOI：

  10.1016/0040-4039(95)00088-t
• 作为产物：
  描述：

  [(S)-2-Oxo-5-phenyl-morpholin-(3Z)-ylidene]-acetic acid methyl ester 在 palladium dihydroxide 、 palladium on activated charcoal 硼烷四氢呋喃络合物 、 氢气 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 7.0h， 生成 (2S,3S)-piperidine-2,3-dicarboxylic acid 3-methyl ester
  参考文献：
  名称：

  Enantioselective Synthesis of Conformationally Restricted Analogs of NMDA:  cis- and trans-Piperidine-2,3-dicarboxylic Acids and Methylated Derivatives

  摘要：

  Various enantiopure stereoisomeric cyclic amino diacids belonging to the 2,3-piperidinedicarboxylic acid series mere obtained via an aza-annulation reaction between enamino esters and acryloyl, methacryloyl, or crotonyl chloride. Enantioselective syntheses of these conformationnally restricted analogs of N-methyl-D-aspartic acid were realized owing to a chiral induction originated from (2S)-2-phenylglycinol. New information about the mechanism of the aza-annulation process is inferred from AM1 calculations which were performed in order to explain the steroselectivity displayed during the formation of the C-4 stereocenter In compound 4.

  DOI：

  10.1021/jo9606158

文献信息

• Neuromediator analogs: Synthesis of cis (2R,3S) and trans (2S,3S)-2,3-piperidine dicarboxylic acids from (2S)-2-phenylglycinol
  作者：Claude Agami、Catherine Kadouri-Puchot、Valérie Le Guen、Jacqueline Vaissermann

  DOI：10.1016/0040-4039(95)00088-t

  日期：1995.3

  The cis and trans isomers of 2,3-piperidine dicarboxylic acids were obtained in enantiopure forms from the same chiral inductor: 2-phenylglycinol. This synthesis was mainly based on a δ-lactam formation via Stille's aza-annulation/hydrogenation procedure which includes here an asymmetric induction.

  从相同的手性引发剂：2-苯基甘氨醇以对映纯形式获得2，3-哌啶二羧酸的顺式和反式异构体。该合成主要基于经由Stille的氮杂-环化/氢化程序的δ-内酰胺形成，该程序在此包括不对称诱导。
• Enantioselective Synthesis of Conformationally Restricted Analogs of NMDA:  <i>cis</i>- and <i>trans</i>-Piperidine-2,3-dicarboxylic Acids and Methylated Derivatives
  作者：Claude Agami、Louis Hamon、Catherine Kadouri-Puchot、Valérie Le Guen

  DOI：10.1021/jo9606158

  日期：1996.1.1

  Various enantiopure stereoisomeric cyclic amino diacids belonging to the 2,3-piperidinedicarboxylic acid series mere obtained via an aza-annulation reaction between enamino esters and acryloyl, methacryloyl, or crotonyl chloride. Enantioselective syntheses of these conformationnally restricted analogs of N-methyl-D-aspartic acid were realized owing to a chiral induction originated from (2S)-2-phenylglycinol. New information about the mechanism of the aza-annulation process is inferred from AM1 calculations which were performed in order to explain the steroselectivity displayed during the formation of the C-4 stereocenter In compound 4.