rel-(3aS,5R,5aS)-3a-benzoyl-5-ethoxy-3a,4,5,5a-tetrahydro-1-methyl-5a-phenylcyclobutapyrrole-2,3-dione

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: rel-(3aS,5R,5aS)-3a-benzoyl-5-ethoxy-3a,4,5,5a-tetrahydro-1-methyl-5a-phenylcyclobutapyrrole-2,3-dione
• 英文别名: (1S,5S,7R)-5-benzoyl-7-ethoxy-2-methyl-1-phenyl-2-azabicyclo[3.2.0]heptane-3,4-dione
• 化学式: C₂₂H₂₁NO₄
• 分子量: 363.413
• InChiKey: NUMDNQFVSCOSHW-VOQZNFBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-benzoyl-5-phenyl-furan-2,3-dione 以 乙二醇二甲醚 、 甲苯 为溶剂， 反应 3.5h， 生成 rel-(3aS,5R,5aS)-3a-benzoyl-5-ethoxy-3a,4,5,5a-tetrahydro-1-methyl-5a-phenylcyclobutapyrrole-2,3-dione
  参考文献：
  名称：

  Regio- and stereoselective photocycloadditions of heterocyclic 2,3-diones — Evidence for an unexpected 1,2-aroyl migration

  摘要：

  Photocyclization of the heterocyclic 2,3-diones 1a-d with electron rich alkenes affords regio- and stereoselectively the 2+2 adducts 2, from Ib with benzophenone as photosensitizer also the Paterno-Buchi adduct 3 is obtained. Similarly, with phenylethyne the cycloadducts 4 are formed in moderate to low yields, in case of Ic the azepinone 6 is the only reaction product. Thermolysis of 4a generates the pyrono compound 5. Irradiation of the N-arylpyrrolediones le, f and ethylvinyl ether give furo[3,2-c]pyrrolones 7 thus making evident an unexpected 1,2-benzoyl migration. Structural elucidation of all ring systems described is based upon X-ray analyses of 2d, 5 and 7f, respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00078-2

文献信息

• Regio- and stereoselective photocycloadditions of heterocyclic 2,3-diones — Evidence for an unexpected 1,2-aroyl migration
  作者：G. Kollenz、E. Terpetschnig、H. Sterk、K. Peters、E.-M. Peters

  DOI：10.1016/s0040-4020(99)00078-2

  日期：1999.3

  Photocyclization of the heterocyclic 2,3-diones 1a-d with electron rich alkenes affords regio- and stereoselectively the 2+2 adducts 2, from Ib with benzophenone as photosensitizer also the Paterno-Buchi adduct 3 is obtained. Similarly, with phenylethyne the cycloadducts 4 are formed in moderate to low yields, in case of Ic the azepinone 6 is the only reaction product. Thermolysis of 4a generates the pyrono compound 5. Irradiation of the N-arylpyrrolediones le, f and ethylvinyl ether give furo[3,2-c]pyrrolones 7 thus making evident an unexpected 1,2-benzoyl migration. Structural elucidation of all ring systems described is based upon X-ray analyses of 2d, 5 and 7f, respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.