(2S,3S,4S)-4-butyl-2-methyl-2,3-dihydropyran-3,4-diol | 61199-74-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4S)-4-butyl-2-methyl-2,3-dihydropyran-3,4-diol
• CAS: 61199-74-4
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: CXNBJUZQKNVEHU-GUBZILKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S)-4-butyl-2-methyl-2,3-dihydropyran-3,4-diol 、 N-甲基苯胺 在 indium(III) bromide 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以76%的产率得到2-butyl-5-methyl-4-(methyl(phenyl)amino)cyclopent-2-enone
  参考文献：
  名称：

  InBr₃-Catalyzed Glycosidation of Glycals with Arylamines: An Alternative Approach To Access 4-Aminocyclopent-2-enones

  摘要：

  To turn side products into major products, a novel strategy to access biologically active 4-aminocyclopent-2-enones was developed. These compounds were originally identified as side products but became major products when 3,5-dimethylpyran-3,4-diol 7a was used as the substrate and 30% InBr3 as the catalyst. Aryl- or heteroarylamines as well as variously substituted glycals can be used in this reaction, and the corresponding 4-aminocyclopent-2-enones were obtained in moderate to good yields. These compounds can be further used to prepare 4-aminocarbocyclic nucleosides.

  DOI：

  10.1021/jo200243d