5-Acetylamino-1-benzyl-2-methyl-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid ethyl ester | 185856-12-6

• 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: 5-Acetylamino-1-benzyl-2-methyl-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid ethyl ester
• 英文别名: Ethyl 3-acetamido-1-benzyl-6-methyl-2-oxo-3,4-dihydropyridine-5-carboxylate
• CAS: 185856-12-6
• 化学式: C₁₈H₂₂N₂O₄
• 分子量: 330.384
• InChiKey: MYEJMWFSZQDBKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-Acetylamino-1-benzyl-2-methyl-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid ethyl ester 在 氢氧化钾 、 氯甲酸乙酯 、 sodium hydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 水 、 甲苯 为溶剂， 反应 16.0h， 生成 (R)-[(5-Acetylamino-1-benzyl-2-methyl-6-oxo-1,6-dihydro-pyridine-3-carbonyl)-amino]-phenyl-acetic acid ethyl ester
  参考文献：
  名称：

  Formation of Dihydropyridone- and Pyridone-Based Peptide Analogs through Aza-Annulation of β-Enamino Ester and Amide Substrates with α-Amido Acrylate Derivatives

  摘要：

  The aza-annulation of beta-enamino ester and amide substrates with the mixed anhydride of 2-acetamidoacrylic acid was used for the efficient construction of highly substituted alpha-acetamido delta-lactam products. With the alpha-acetamido substituent, lactam functionality, and gamma-carboxylate group, these delta-lactam products represent an interesting class of conformationally restricted dipeptide analogs. The framework of this lactam hub is structurally related to that of an alpha-amino acid coupled with a beta-amino acid. When alpha-amino esters derived from naturally occurring amino acids were used in the enamine formation step, subsequent aza-annulation led to branched peptide surrogates with two C-termini that extended from a common N-terminus. Oxidation of the aza-annulation products resulted in the generation of a planar system with peptide functionality radiating from the 1, 3, and 5 positions of the pyridone hub. Alternatively, pyridone products could be formed directly from the enamino amides by reaction with 2-phenyl-4-(ethoxymethylene)oxazolone. Subsequent hydrolysis of the acetamido and ester substituents of the N-benzylpyridones was selectively performed to access unique beta-amino acid products. Formation of the mixed anhydride of this acid, followed by amide bond formation with the ester of an alpha-amino acid, allowed extension of the peptide chain from the dihydropyridone structure.

  DOI：

  10.1021/jo9600520
• 作为产物：
  描述：

  ethyl (Z)-3-(benzylamino)-2-butenoate 、 sodium;N-(1-carboxyethenyl)ethanimidate 在 氯甲酸乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 生成 5-Acetylamino-1-benzyl-2-methyl-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Formation of Dihydropyridone- and Pyridone-Based Peptide Analogs through Aza-Annulation of β-Enamino Ester and Amide Substrates with α-Amido Acrylate Derivatives

  摘要：

  The aza-annulation of beta-enamino ester and amide substrates with the mixed anhydride of 2-acetamidoacrylic acid was used for the efficient construction of highly substituted alpha-acetamido delta-lactam products. With the alpha-acetamido substituent, lactam functionality, and gamma-carboxylate group, these delta-lactam products represent an interesting class of conformationally restricted dipeptide analogs. The framework of this lactam hub is structurally related to that of an alpha-amino acid coupled with a beta-amino acid. When alpha-amino esters derived from naturally occurring amino acids were used in the enamine formation step, subsequent aza-annulation led to branched peptide surrogates with two C-termini that extended from a common N-terminus. Oxidation of the aza-annulation products resulted in the generation of a planar system with peptide functionality radiating from the 1, 3, and 5 positions of the pyridone hub. Alternatively, pyridone products could be formed directly from the enamino amides by reaction with 2-phenyl-4-(ethoxymethylene)oxazolone. Subsequent hydrolysis of the acetamido and ester substituents of the N-benzylpyridones was selectively performed to access unique beta-amino acid products. Formation of the mixed anhydride of this acid, followed by amide bond formation with the ester of an alpha-amino acid, allowed extension of the peptide chain from the dihydropyridone structure.

  DOI：

  10.1021/jo9600520