[4S-4α,8α]-1,6-dioxo-8-methyl-4-phenyl-1,3,4,6,7,8-hexahydropyrido[2,1-c][1,4]oxazine-9-carboxylic acid methyl ester | 181638-38-0

• 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: [4S-4α,8α]-1,6-dioxo-8-methyl-4-phenyl-1,3,4,6,7,8-hexahydropyrido[2,1-c][1,4]oxazine-9-carboxylic acid methyl ester
• 英文别名: methyl (4S,8S)-8-methyl-1,6-dioxo-4-phenyl-3,4,7,8-tetrahydropyrido[2,1-c][1,4]oxazine-9-carboxylate
• CAS: 181638-38-0
• 化学式: C₁₇H₁₇NO₅
• 分子量: 315.326
• InChiKey: IWKADLZIQQRCLU-CMPLNLGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [4S-4α,8α]-1,6-dioxo-8-methyl-4-phenyl-1,3,4,6,7,8-hexahydropyrido[2,1-c][1,4]oxazine-9-carboxylic acid methyl ester 在 palladium dihydroxide 、 palladium on activated charcoal 硼烷四氢呋喃络合物 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 4.0h， 生成 (2R,3S,4S)-4-methylpiperidine-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
• 作为产物：
  描述：

  L-苯甘氨醇 以 四氢呋喃 为溶剂， 反应 240.0h， 生成 [4S-4α,8α]-1,6-dioxo-8-methyl-4-phenyl-1,3,4,6,7,8-hexahydropyrido[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