3-benzoyl-5,6-diphenylpyran-2-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-benzoyl-5,6-diphenylpyran-2-one
• 化学式: C₂₄H₁₆O₃
• 分子量: 352.389
• InChiKey: FRFHLDAILXFUAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-benzoyl-5-phenyl-furan-2,3-dione 以 甲苯 、 乙腈 为溶剂， 反应 5.5h， 生成 3-benzoyl-5,6-diphenylpyran-2-one
  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

• Synthesis of 3,5,6-trisubstituted α-pyrones from Baylis–Hillman adducts
  作者：Seong Jin Kim、Hyun Seung Lee、Jae Nyoung Kim

  DOI：10.1016/j.tetlet.2006.11.180

  日期：2007.2

  3,5,6-Trisubstituted α-pyrones were synthesized starting from the Baylis–Hillman adducts. The synthesis was carried out via the sequential introduction of ketone at the primary position of Baylis–Hillman adduct, lactonization, and the following oxidation with PCC.

  从Baylis-Hillman加合物开始合成3,5,6-三取代的α-吡喃酮。合成是通过在Baylis-Hillman加合物的主要位置依次引入酮，内酯化以及随后的PCC氧化来进行的。
• 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.