5-Acetylamino-1-benzyl-6-oxo-2-[1-phenyl-meth-(E)-ylidene]-piperidine-3-carboxylic acid ethyl ester | 185856-25-1

• 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-6-oxo-2-[1-phenyl-meth-(E)-ylidene]-piperidine-3-carboxylic acid ethyl ester
• 英文别名: ethyl 5-acetamido-1-benzyl-2-benzylidene-6-oxopiperidine-3-carboxylate
• CAS: 185856-25-1
• 化学式: C₂₄H₂₆N₂O₄
• 分子量: 406.481
• InChiKey: LJMCRLUOKCNXCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  75.71
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-Acetylamino-1-benzyl-6-oxo-2-[1-phenyl-meth-(E)-ylidene]-piperidine-3-carboxylic acid ethyl ester 在 palladium on activated charcoal 氢气 、 sodium carbonate 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以94%的产率得到(2R,3R)-5-Acetylamino-1,2-dibenzyl-6-oxo-piperidine-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
• 作为产物：
  描述：

  4-phenylbut-2-ynoic acid ethyl ester 在 三氟化硼乙醚 、 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-6-oxo-2-[1-phenyl-meth-(E)-ylidene]-piperidine-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