tert-butyl N-[(1S)-1-[(2R)-1-(4-methylphenyl)-3,4-dioxoazetidin-2-yl]ethyl]carbamate | 159612-07-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丁烷
• 英文名称: tert-butyl N-[(1S)-1-[(2R)-1-(4-methylphenyl)-3,4-dioxoazetidin-2-yl]ethyl]carbamate
• CAS: 159612-07-4
• 化学式: C₁₇H₂₂N₂O₄
• 分子量: 318.373
• InChiKey: LVTWBCMMPURQPQ-WCQYABFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  tert-butyl N-[(1S)-1-[(2R)-1-(4-methylphenyl)-3,4-dioxoazetidin-2-yl]ethyl]carbamate 在 三甲基氯硅烷 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 生成 methyl (2R,3S)-3-amino-2-(4-methylanilino)butanoate
  参考文献：
  名称：

  New Synthesis of .alpha.-Amino Acid N-Carboxy Anhydrides through Baeyer-Villiger Oxidation of .alpha.-Keto .beta.-Lactams

  摘要：

  A conceptually new route for the generation of optically active alpha-aminoacid N-carboxy anhydrides (NCAs) and hence alpha-amino acid derivatives is described. The strategy developed is simple and consists of the oxidation of alpha-hydroxy beta-lactams to the corresponding alpha-keto beta-lactams followed by a Baeyer-Villiger rearrangement. By that means, a wide variety of functionalized alpha-aminoacid N-carboxy anhydrides can be obtained, i.e., alpha,beta-diamino acid and alpha-amino beta-hydroxy acid-derived NCAs. The starting alpha-hydroxy(alkoxy) beta-lactams required for the study are easily prepared in large quantities either by the cycloaddition reaction of achiral alkoxyketenes with chiral aldehyde-derived imines or by the addition of Grignard reagents to a 3-(benzyloxy)-4-formylazetidin-2-one. The construction of a wide variety of NCA's from non-amino acid precursors becomes the most remarkable point of the reaction methodology developed.

  DOI：

  10.1021/jo00090a033
• 作为产物：
  描述：

  tert-butyl N-[(1S)-1-[(2R,3S)-3-hydroxy-1-(4-methylphenyl)-4-oxoazetidin-2-yl]ethyl]carbamate 在 phosphorus pentoxide 、 二甲基亚砜 作用下， 反应 16.0h， 以75%的产率得到tert-butyl N-[(1S)-1-[(2R)-1-(4-methylphenyl)-3,4-dioxoazetidin-2-yl]ethyl]carbamate
  参考文献：
  名称：

  New Synthesis of .alpha.-Amino Acid N-Carboxy Anhydrides through Baeyer-Villiger Oxidation of .alpha.-Keto .beta.-Lactams

  摘要：

  A conceptually new route for the generation of optically active alpha-aminoacid N-carboxy anhydrides (NCAs) and hence alpha-amino acid derivatives is described. The strategy developed is simple and consists of the oxidation of alpha-hydroxy beta-lactams to the corresponding alpha-keto beta-lactams followed by a Baeyer-Villiger rearrangement. By that means, a wide variety of functionalized alpha-aminoacid N-carboxy anhydrides can be obtained, i.e., alpha,beta-diamino acid and alpha-amino beta-hydroxy acid-derived NCAs. The starting alpha-hydroxy(alkoxy) beta-lactams required for the study are easily prepared in large quantities either by the cycloaddition reaction of achiral alkoxyketenes with chiral aldehyde-derived imines or by the addition of Grignard reagents to a 3-(benzyloxy)-4-formylazetidin-2-one. The construction of a wide variety of NCA's from non-amino acid precursors becomes the most remarkable point of the reaction methodology developed.

  DOI：

  10.1021/jo00090a033

文献信息

• New Synthesis of .alpha.-Amino Acid N-Carboxy Anhydrides through Baeyer-Villiger Oxidation of .alpha.-Keto .beta.-Lactams
  作者：Claudio Palomo、Jesus M. Aizpurua、Inaki Ganboa、Francois Carreaux、Carmen Cuevas、Elena Maneiro、Jesus M. Ontoria

  DOI：10.1021/jo00090a033

  日期：1994.6

  A conceptually new route for the generation of optically active alpha-aminoacid N-carboxy anhydrides (NCAs) and hence alpha-amino acid derivatives is described. The strategy developed is simple and consists of the oxidation of alpha-hydroxy beta-lactams to the corresponding alpha-keto beta-lactams followed by a Baeyer-Villiger rearrangement. By that means, a wide variety of functionalized alpha-aminoacid N-carboxy anhydrides can be obtained, i.e., alpha,beta-diamino acid and alpha-amino beta-hydroxy acid-derived NCAs. The starting alpha-hydroxy(alkoxy) beta-lactams required for the study are easily prepared in large quantities either by the cycloaddition reaction of achiral alkoxyketenes with chiral aldehyde-derived imines or by the addition of Grignard reagents to a 3-(benzyloxy)-4-formylazetidin-2-one. The construction of a wide variety of NCA's from non-amino acid precursors becomes the most remarkable point of the reaction methodology developed.