2-Methyl-3-(1,2-O-isopropylidene-α-D-xylo-tetrofuranos-4-yl)-5-(2,6-dimethylphenyl)-4,6-dioxo-2,3,3a,4,6,6a-hexahydropyrrolo<3,4-d>isoxazole | 146815-01-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 2-Methyl-3-(1,2-O-isopropylidene-α-D-xylo-tetrofuranos-4-yl)-5-(2,6-dimethylphenyl)-4,6-dioxo-2,3,3a,4,6,6a-hexahydropyrrolo<3,4-d>isoxazole
• CAS: 146815-01-2
• 化学式: C₂₁H₂₆N₂O₇
• 分子量: 418.447
• InChiKey: ZEFASWPLXVLEMR-OXPRTTQYSA-N

物化性质

• 熔点：
  145-147 °C
• 沸点：
  630.5±65.0 °C(predicted)
• 密度：
  1.345±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.64
• 重原子数：
  30.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  97.77
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  1-(2,6-二甲基苯基)-1H-吡咯-2,5-二酮 、 1,2-O-isopropylidene-α-D-xylo-pentodialdo-1,4-furanose 5-(N-methyloxime) 以 甲苯 为溶剂， 反应 1.0h， 以78%的产率得到2-Methyl-3-(1,2-O-isopropylidene-α-D-xylo-tetrofuranos-4-yl)-5-(2,6-dimethylphenyl)-4,6-dioxo-2,3,3a,4,6,6a-hexahydropyrrolo<3,4-d>isoxazole
  参考文献：
  名称：

  Preparation and stereoselectivity of 1,3-dipolar cycloaddition of C-glycosyl nitrones to N-arylmaleimides

  摘要：

  The cycloaddition of 3'-hydroxyglycosyl-N-methylnitrone (1) to N-arylmaleimides gave the syn isoxazolidines 6, whereas 3'-acetoxyglycosyl-N-methylnitrone (2) afforded the anti isoxazolidines 8 and 10. The formation of 6 was rationalized by an exo attack, stereoelectronically preferred through the hydrogen bond between the pentose hydroxyl group and one of the carbonyl groups of N-arylmaleimide. The sterically preferred endo attack avoiding the repulsions between N-arylmaleimide and sugar moiety was proposed for addition of 2. The structure and steric configuration of the products have been assigned on the basis of H-1 and C-13-NMR spectroscopy, mainly by nuclear Overhauser effect difference spectroscopy. AM1 calculations of the nitrones and MM2 calculations of the adducts were performed.

  DOI：

  10.1007/bf00810931