(S)-4,4-dichloro-3-isopropylisoxazolidin-5-one | 1301708-25-7

• 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: (S)-4,4-dichloro-3-isopropylisoxazolidin-5-one
• 英文别名: (3S)-4,4-dichloro-3-propan-2-yl-1,2-oxazolidin-5-one
• CAS: 1301708-25-7
• 化学式: C₆H₉Cl₂NO₂
• 分子量: 198.049
• InChiKey: BVLUNQUKSDFEJV-BYPYZUCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-4,4-dichloro-3-isopropylisoxazolidin-5-one 在 potassium oxalate 作用下， 以 甲醇 、 水 为溶剂， 反应 44.0h， 生成 (S)-4-methyl-2-oxo-3-(2-phenylacetamido)pentanoic acid
  参考文献：
  名称：

  α,α-Dichloroisoxazolidinones for the Synthesis and Chemoselective Peptide Ligation of α-Peptide α-Ketoacids

  摘要：

  In seeking to develop an iterative approach to the preparation of alpha-oligopeptides by the chemoselective amide-forming coupling of alpha-ketoacids and hydroxylamines, we have designed and synthesized novel enantiopure monomers. Key to our approach is the use of alpha,alpha-dichloroacids as masked alpha-ketoacids. The preparation of these monomers, their coupling with alpha-ketoacids, and the conversion of the alpha,alpha-dichloroacids to alpha-ketoacids is described. These studies provide a first step to a conceptually unique approach to peptide synthesis that does not require activating reagents or produce chemical byproducts.

  DOI：

  10.3987/com-10-s(e)106
• 作为产物：
  描述：

  (S)-4,4-dichloro-2-((3aR,4R,6S,6aR)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-3-isopropylisoxazolidin-5-one 在 高氯酸 作用下， 以 水 、 乙腈 为溶剂， 反应 1.5h， 以72%的产率得到(S)-4,4-dichloro-3-isopropylisoxazolidin-5-one
  参考文献：
  名称：

  α,α-Dichloroisoxazolidinones for the Synthesis and Chemoselective Peptide Ligation of α-Peptide α-Ketoacids

  摘要：

  In seeking to develop an iterative approach to the preparation of alpha-oligopeptides by the chemoselective amide-forming coupling of alpha-ketoacids and hydroxylamines, we have designed and synthesized novel enantiopure monomers. Key to our approach is the use of alpha,alpha-dichloroacids as masked alpha-ketoacids. The preparation of these monomers, their coupling with alpha-ketoacids, and the conversion of the alpha,alpha-dichloroacids to alpha-ketoacids is described. These studies provide a first step to a conceptually unique approach to peptide synthesis that does not require activating reagents or produce chemical byproducts.

  DOI：

  10.3987/com-10-s(e)106