4'-chloro-3-(4-chlorobenzoyl)-5-hydroxyflavone | 196610-57-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 高异黄酮
• 英文名称: 4'-chloro-3-(4-chlorobenzoyl)-5-hydroxyflavone
• 英文别名: 3-(4-chlorobenzoyl)-5-hydroxy-4'-chloroflavone；3-(4-chlorobenzoyl)-2-(4-chlorophenyl)-5-hydroxychromen-4-one
• CAS: 196610-57-8
• 化学式: C₂₂H₁₂Cl₂O₄
• 分子量: 411.241
• InChiKey: TZHKDLFGBMQLIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4'-chloro-3-(4-chlorobenzoyl)-5-hydroxyflavone 在 potassium carbonate 作用下， 反应 12.0h， 生成 4'-Chloro-5-hydroxyflavone
  参考文献：
  名称：

  3-Aroyl-5-hydroxyflavones: Synthesis and Transformation into Aroylpyrazoles

  摘要：

  DOI：

  10.1002/1099-0690(200211)2002:22<3807::aid-ejoc3807>3.0.co;2-2
• 作为产物：
  描述：

  2,6-二羟基苯乙酮 在 吡啶 、 potassium carbonate 作用下， 以 吡啶 为溶剂， 反应 14.0h， 生成 4'-chloro-3-(4-chlorobenzoyl)-5-hydroxyflavone
  参考文献：
  名称：

  3-Aroyl-5-hydroxyflavones: Synthesis and Transformation into Aroylpyrazoles

  摘要：

  DOI：

  10.1002/1099-0690(200211)2002:22<3807::aid-ejoc3807>3.0.co;2-2

文献信息

• An Efficient One-Pot Synthesis and Anticancer Activity of 4'-Substituted Flavonoids
  作者：X. Wang、J. Liu、Y. Zhang

  DOI：10.1134/s1070363218050328

  日期：2018.5

  A number of 4'-substituted (R = H, Me, Cl, F) flavone derivatives is synthesized from 2-hydroxyacetophenones using the modified Baker–Venkataraman reaction. Compound [3-(4-fluorobenzoyl)-5- hydroxy-4'-fluoroflavone] was synthesized for the first time with the yield of 12%. Antiproliferative assays indicate that the synthesized flavones with F substituent at the 4' position demonstrate higher activity

  使用修饰的Baker-Venkataraman反应，由2-羟基苯乙酮合成了许多4'-取代的（R = H，Me，Cl，F）黄酮衍生物。首次合成化合物[3-（4-氟苯甲酰基）-5-羟基-4'-氟黄酮]，产率为12％。抗增殖试验表明，合成的黄酮在4'位具有F取代基，显示出比其他黄酮衍生物更高的活性，特别是针对HeLa和MCF-7的IC 50为9.5和2.7μM。
• 3-Aroyl-5-hydroxyflavones: synthesis and mechanistic studies by mass spectrometry
  作者：Ana M. Cardoso、Artur M. S. Silva、Cristina M. F. Barros、Lúcia M. P. M. Almeida、A. J. Ferrer-Correia、José A. S. Cavaleiro

  DOI：10.1002/(sici)1096-9888(199709)32:9<930::aid-jms549>3.0.co;2-e

  日期：1997.9

  The synthesis and mass spectra of three 3-aroyl-5-hydroxyflavones are reported. The interpretation of the mechanistic pathways for the fragmentation of the metastable molecular ions of these compounds was achieved through the analysis of their mass-analysed ion kinetic energy (MIKE) spectra and of the B-2/E spectra of a few fragment ions. Labelling of the hydroxyl proton with deuterium and the analysis of the MIKE spectra of a model compound with chlorine atoms in the 2',6'- and 2 '',6 ''-positions led to a mechanism for the losses of OH. and HCO. which involves hydrogen migration from the 2 ''- or 6 ''-position to the 4-carbonyl oxygen atom. A mechanism for the loss of a neutral molecule of anisole from the molecular ion of the 3-aroyl-5-hydroxyflavone with a methoxyl group in the 4'- and 4 ''-positions is also suggested. For the flavones with hydrogen or chlorine substituents at these positions, loss of a phenyl (or chlorophenyl) radical occurs instead. (C) 1997 by John Wiley & Sons, Ltd.
• 3-Aroyl-5-hydroxyflavones: Synthesis and Transformation into Aroylpyrazoles
  作者：Diana C. G. A. Pinto、Artur M. S. Silva、Lúcia M. P. M. Almeida、José A. S. Cavaleiro、José Elguero

  DOI：10.1002/1099-0690(200211)2002:22<3807::aid-ejoc3807>3.0.co;2-2

  日期：2002.11