C-(4-chlorophenyl)-N-(D-glucoso)-nitrone | 154512-80-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: C-(4-chlorophenyl)-N-(D-glucoso)-nitrone
• CAS: 154512-80-8；154512-81-9
• 化学式: C₁₃H₁₆ClNO₆
• 分子量: 317.726
• InChiKey: NUUYYVLITNPZAP-ARDSGTFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.93
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  116.22
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-(2,6-二甲基苯基)-1H-吡咯-2,5-二酮 、 C-(4-chlorophenyl)-N-(D-glucoso)-nitrone 以 乙醇 为溶剂， 反应 48.0h， 以30%的产率得到(3R,3aR,6aS)-2-(D-glucoso)-3-(4-chlorophenyl)-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 ofD-glucose-derived nitrones to N-arylmaleimides

  摘要：

  Nitrones 2 derived from D-glucose oxime and benzaldehydes without employing any protection of hydroxyl group were isolated in pure state. The 1,3-dipolar cycloaddition of 2 to N-arylmaleimides gave predominantly the anti isoxazolidines 3 and was rationalized by Z/E isomerization of N-glycosylnitrones 2. The structure and steric configuration of the products have been assigned on the basis of H-1- and C-13-NMR spectroscopy. AM1 calculations of the nitrones and MM2 calculations of the adducts were performed.

  DOI：

  10.1007/bf00814148
• 作为产物：
  描述：

  可得然胶 在 盐酸羟胺 、 sodium methylate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 2.0h， 生成 C-(4-chlorophenyl)-N-(D-glucoso)-nitrone
  参考文献：
  名称：

  Preparation and stereoselectivity of 1,3-dipolar cycloaddition ofD-glucose-derived nitrones to N-arylmaleimides

  摘要：

  Nitrones 2 derived from D-glucose oxime and benzaldehydes without employing any protection of hydroxyl group were isolated in pure state. The 1,3-dipolar cycloaddition of 2 to N-arylmaleimides gave predominantly the anti isoxazolidines 3 and was rationalized by Z/E isomerization of N-glycosylnitrones 2. The structure and steric configuration of the products have been assigned on the basis of H-1- and C-13-NMR spectroscopy. AM1 calculations of the nitrones and MM2 calculations of the adducts were performed.

  DOI：

  10.1007/bf00814148