4-benzoyl-2,3-dihydro-1H-5-phenylpyrrole-2,3-dione | 61350-69-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 4-benzoyl-2,3-dihydro-1H-5-phenylpyrrole-2,3-dione
• 英文别名: 4-benzoyl-5-phenyl-1H-pyrrole-2,3-dione；4-benzoyl-5-phenyl-pyrrole-2,3-dione；4-Benzoyl-2,3-dioxo-5-phenyl-2,3-dihydropyrrol
• CAS: 61350-69-4
• 化学式: C₁₇H₁₁NO₃
• 分子量: 277.279
• InChiKey: BNYWGBYTAQQZAD-UHFFFAOYSA-N

物化性质

• 熔点：
  175 °C
• 密度：
  1.331±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.98
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.24
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-benzoyl-2,3-dihydro-1H-5-phenylpyrrole-2,3-dione 以 gas 为溶剂， 500.0 ℃ 、0.01 Pa 条件下， 生成 2-(Imino-phenyl-methyl)-3-phenyl-propene-1,3-dione
  参考文献：
  名称：

  Reactive nitrogenous molecules from Meldrum's acid derivatives, pyrrole-2,3-diones, and isoxazolones

  摘要：

  DOI：

  10.1021/jo00189a025
• 作为产物：
  描述：

  4-benzoyl-5-phenyl-furan-2,3-dione 在 氨 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以73%的产率得到4-benzoyl-2,3-dihydro-1H-5-phenylpyrrole-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

• Chemoselective [3 + 2] annulation of oxime acetate with 2-aryl-3-ethoxycarbonyl-pyrroline-4,5-dione: an entry to pyrrolo[2,3-<i>b</i>]pyrrole derivatives
  作者：Andhavaram Ramaraju、Atul Upare、Ewan W Blanch、Subashani Maniam、Balasubramanian Sridhar、Surendar Reddy Bathula、Chada Raji Reddy

  DOI：10.1039/d1ob00990g

  日期：——

  A novel chemoselective [3 + 2] annulation reaction of easily accessible ketoxime acetate with 2-aryl-3-ethoxycarbonyl pyrroline-4,5-dione has been developed for the synthesis of unknown pyrrolo[2,3-b]pyrrole frameworks. This method involves copper-mediated N–O bond cleavage followed by the formation of carbon–carbon and carbon–nitrogen bonds. This operationally simple protocol provides broader functional

  已经开发了一种易于获得的醋酸酮肟与 2-aryl-3-ethoxycarbonyl pyrroline-4,5-dione 的新型化学选择性 [3 + 2] 环化反应，用于合成未知的 pyrrolo[2,3- b ] 吡咯骨架。该方法涉及铜介导的 N-O 键断裂，然后形成碳-碳和碳-氮键。这种操作简单的协议提供了更广泛的功能组兼容性和良好的产量。
• BRIEHL, H.;LUKOSCH, A.;WENTRUP, C., J. ORG. CHEM., 1984, 49, N 15, 2772-2779
  作者：BRIEHL, H.、LUKOSCH, A.、WENTRUP, C.

  DOI：——

  日期：——
• OTT W.; KOLLENZ G.; ZIEGLER E., SYNTHESIS <SYNT-BF>, 1976, NO 8, 546-547
  作者：OTT W.、 KOLLENZ G.、 ZIEGLER E.

  DOI：——

  日期：——
• Reactive nitrogenous molecules from Meldrum's acid derivatives, pyrrole-2,3-diones, and isoxazolones
  作者：Horst Briehl、Adelheid Lukosch、Curt Wentrup

  DOI：10.1021/jo00189a025

  日期：1984.7
• 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.