methyl (3aS,6aR)-4,6-dioxo-5-phenyl-4,5,6,6a-tetrahydro-3aH-pyrrolo[3,4-d]isoxazole-3-carboxylate

• 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: methyl (3aS,6aR)-4,6-dioxo-5-phenyl-4,5,6,6a-tetrahydro-3aH-pyrrolo[3,4-d]isoxazole-3-carboxylate
• 英文别名: methyl (3aS,6aR)-4,6-dioxo-5-phenyl-3a,6a-dihydropyrrolo[3,4-d][1,2]oxazole-3-carboxylate
• 化学式: C₁₃H₁₀N₂O₅
• 分子量: 274.233
• InChiKey: KBVIPRCJINMKIJ-WCBMZHEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  85.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-苯基马来酰亚胺 、 2,5-bis(methoxycarbonyl)-3,4-diazacyclopentadienone dioxide 以 苯 为溶剂， 以17%的产率得到
  参考文献：
  名称：

  Role of CH/O and CH/π Interactions in Structural Stability. Effect on Endo Selectivity in 1,3-Dipolar Reaction of Electron-Deficient 4-Oxo-4H-pyrazole 1,2-Dioxide with N-Substituted Maleimides

  摘要：

  The molecular structure of the 1:2 cycloadduct derived from 1,3-dipolar reaction of 3,5-bis(methoxycarbonyl)-4-oxo-4H-pyrazole 1,2-dioxide (1a) with N-phenyl maleimide (2a) was established to be an anti-endo-endo form by the single crystal X-ray analysis. The weak attractive CH/O interaction between la and 2a is conjectured to play an important role in the preferential formation of the endo transition-state. The formation mechanism of the adduct is discussed on the basis of transition-state structures optimized at the B3LYP/6-31G(d) level of theory.

  DOI：

  10.3987/com-12-12623