endo-3b-phenyl-2,5-di-p-tolyl-hexahydro-7-oxa-2,5,6a-triaza-cyclopenta[a]pentalene-1,3-dione

• 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: endo-3b-phenyl-2,5-di-p-tolyl-hexahydro-7-oxa-2,5,6a-triaza-cyclopenta[a]pentalene-1,3-dione
• 英文别名: (1S,2R,8R)-4,10-bis(4-methylphenyl)-2-phenyl-7-oxa-4,6,10-triazatricyclo[6.3.0.02,6]undecane-9,11-dione
• 化学式: C₂₇H₂₅N₃O₃
• 分子量: 439.514
• InChiKey: AYFHZPQMZNLTCR-XFAFFCHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  33
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  53.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-(4-甲基苯基)-1H-吡咯-2,5-二酮 、 4-phenyl-1-(p-tolyl)-2,5-dihydro-1H-imidazole 3-oxide 以 苯 为溶剂， 反应 10.0h， 以60%的产率得到endo-3b-phenyl-2,5-di-p-tolyl-hexahydro-7-oxa-2,5,6a-triaza-cyclopenta[a]pentalene-1,3-dione
  参考文献：
  名称：

  Dipolar cycloadditions of imidazoline 3-oxides with N-arylmaleimides. Synthesis and diethylamine induced ring-opening of exo and endo hexahydro-7-oxa-2,5,6a-triaza-cyclopenta[a]pentalene-1,3-diones

  摘要：

  14-Diarylimidazoline 3-oxides react with N-arylmaleimides in benzene to give predominantly the corresponding endo adducts. Chiral imidazoline 3-oxides react diastereospecifically (cis configuration of the tetrahydroimidazo ring) and diastereoselectively to give cis-endo adducts. The effects of substituents on the aromatic ring of the maleimide was investigated. The presence of electron-withdrawing or releasing group,; have minor effect on the total yields but more pronounced is the effect on the ratio of exo and endo diastereomers. The adducts undergo an interesting and unprecedented ring-opening in the presence of secondary amines to give deoxygenated 3-imidazoline 3-oxides instead of the expected double cis elimination products. Tertiary amines did not induce any reaction, (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.11.038

文献信息

• Dipolar cycloadditions of imidazoline 3-oxides with N-arylmaleimides. Synthesis and diethylamine induced ring-opening of exo and endo hexahydro-7-oxa-2,5,6a-triaza-cyclopenta[a]pentalene-1,3-diones
  作者：Necdet Coşkun、Habibe Mert、Nevin Arıkan

  DOI：10.1016/j.tet.2005.11.038

  日期：2006.2

  14-Diarylimidazoline 3-oxides react with N-arylmaleimides in benzene to give predominantly the corresponding endo adducts. Chiral imidazoline 3-oxides react diastereospecifically (cis configuration of the tetrahydroimidazo ring) and diastereoselectively to give cis-endo adducts. The effects of substituents on the aromatic ring of the maleimide was investigated. The presence of electron-withdrawing or releasing group,; have minor effect on the total yields but more pronounced is the effect on the ratio of exo and endo diastereomers. The adducts undergo an interesting and unprecedented ring-opening in the presence of secondary amines to give deoxygenated 3-imidazoline 3-oxides instead of the expected double cis elimination products. Tertiary amines did not induce any reaction, (c) 2005 Elsevier Ltd. All rights reserved.