(2S,4R,5R)-2-(2-propyl)-4-hydroxy-5-azido-7-methyloctanoic acid, γ-lactone | 144490-44-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (2S,4R,5R)-2-(2-propyl)-4-hydroxy-5-azido-7-methyloctanoic acid, γ-lactone
• 英文别名: (3S,5R)-5-[(1R)-1-azido-3-methylbutyl]-3-propan-2-yloxolan-2-one
• CAS: 144490-44-8
• 化学式: C₁₂H₂₁N₃O₂
• 分子量: 239.318
• InChiKey: JJLMCSJFMPSXRN-HBNTYKKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  40.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 (2S,4R,5R)-2-(2-propyl)-4-hydroxy-5-azido-7-methyloctanoic acid, γ-lactone 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 以80%的产率得到(2S,4R,5R)-2-(2-propyl)-4-hydroxy-5-<(tert-butyloxycarbonyl)amino>-7-methyloctanoic acid, γ-lactone
  参考文献：
  名称：

  Synthesis of the hydroxyethylene isostere of Leu-Val

  摘要：

  The hydroxyethylene isostere of the dipeptide leu-val was synthesized from isovaleryl aldehyde in nine steps in 15% overall yield without the use of chromatographic separations. A key finding is the ability of an amide to selectively direct an epoxidation in an acyclic system and that the selectivity is a function of the amide's size.

  DOI：

  10.1021/jo00051a005
• 作为产物：
  描述：

  (E)-(S)-2-Isopropyl-7-methyl-oct-4-enoic acid ((S)-1-phenyl-ethyl)-amide 在 PEG 300 、 sodium azide 、 硫酸 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 27.17h， 生成 (2S,4R,5R)-2-(2-propyl)-4-hydroxy-5-azido-7-methyloctanoic acid, γ-lactone
  参考文献：
  名称：

  Synthesis of the hydroxyethylene isostere of Leu-Val

  摘要：

  The hydroxyethylene isostere of the dipeptide leu-val was synthesized from isovaleryl aldehyde in nine steps in 15% overall yield without the use of chromatographic separations. A key finding is the ability of an amide to selectively direct an epoxidation in an acyclic system and that the selectivity is a function of the amide's size.

  DOI：

  10.1021/jo00051a005

文献信息

• Synthesis of the hydroxyethylene isostere of Leu-Val
  作者：Peter G. M. Wuts、Allen R. Ritter、Lynn E. Pruitt

  DOI：10.1021/jo00051a005

  日期：1992.12

  The hydroxyethylene isostere of the dipeptide leu-val was synthesized from isovaleryl aldehyde in nine steps in 15% overall yield without the use of chromatographic separations. A key finding is the ability of an amide to selectively direct an epoxidation in an acyclic system and that the selectivity is a function of the amide's size.