(3R,5S)-5-((R)-1-Hydroxy-3-methyl-butyl)-3-isopropyl-dihydro-furan-2-one

• 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: (3R,5S)-5-((R)-1-Hydroxy-3-methyl-butyl)-3-isopropyl-dihydro-furan-2-one
• 英文别名: (3R,5S)-5-[(1R)-1-hydroxy-3-methylbutyl]-3-propan-2-yloxolan-2-one
• 化学式: C₁₂H₂₂O₃
• 分子量: 214.305
• InChiKey: SOYSKASPSUCNRG-MXWKQRLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (S)-2-((2S,3S)-3-Isobutyl-oxiranylmethyl)-3-methyl-N-((S)-1-phenyl-ethyl)-butyramide 在 硫酸 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 (3R,5R)-5-((S)-1-Hydroxy-3-methyl-butyl)-3-isopropyl-dihydro-furan-2-one 、 (3R,5S)-5-((R)-1-Hydroxy-3-methyl-butyl)-3-isopropyl-dihydro-furan-2-one 、 (2S,4R,5S)-4,5-dihydroxy-2-isopropyl-7-methyloctanoic acid, γ-lactone 、 (2S,4S,5R)-4,5-dihydroxy-2-isopropyl-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.