[(S)-2-Oxo-5-phenyl-morpholin-(3Z)-ylidene]-acetic acid methyl ester | 163191-45-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: [(S)-2-Oxo-5-phenyl-morpholin-(3Z)-ylidene]-acetic acid methyl ester
• 英文别名: methyl (2Z)-2-[(5S)-2-oxo-5-phenylmorpholin-3-ylidene]acetate
• CAS: 163191-45-5
• 化学式: C₁₃H₁₃NO₄
• 分子量: 247.251
• InChiKey: ARIREUUUPLVFGD-ZJRUKIMVSA-N

物化性质

• 沸点：
  465.8±45.0 °C(Predicted)
• 密度：
  1.291±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(S)-2-Oxo-5-phenyl-morpholin-(3Z)-ylidene]-acetic acid methyl ester 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 5.0h， 生成 [4S-4α,8α,9α,9aα]-1,6-dioxo-8-methyl-4-phenyloctahydropyrido[2,1-c][1,4]oxazine-9-carboxylic acid 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
• 作为产物：
  描述：

  L-苯甘氨醇 、 丁炔二酸二甲酯 以88%的产率得到[(S)-2-Oxo-5-phenyl-morpholin-(3Z)-ylidene]-acetic acid 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