4'-Chloro-5-hydroxyflavone

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 4'-Chloro-5-hydroxyflavone
• 英文别名: 5-hydroxy-4'-chloroflavone；2-(4-chlorophenyl)-5-hydroxychromen-4-one
• 化学式: C₁₅H₉ClO₃
• 分子量: 272.688
• InChiKey: RTRDFMNQTNFTKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 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-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 Effective Synthesis of 5,4'-Disubstituted Flavones via a Cesium Enolate Assisted Intramolecular ipso-Substitution Reaction
  作者：Masato Matsugi、Masaki Takeda、Ayano Takahashi、Takahide Tazaki、Hiroto Tamura、Takayuki Shioiri

  DOI：10.1248/cpb.58.1107

  日期：——

  A variety of 5,4′-disubstituted flavones, which are anticipated to be androgen receptor antagonists to treat diseases mediated by the androgen receptor, were synthesized. It was found that an intramolecular ipso-substitution reaction via cesium enolate using 2-fluoro-6-hydroxyacetophenone and various benzoyl chlorides was effective in the preparation of 5-hydroxy-4′-alkylflavones.

  合成了一系列5,4′-二取代黄酮，预计其为雄激素受体拮抗剂，用于治疗由雄激素受体介导的疾病。研究发现，通过铯烯醇与2-氟-6-羟基乙酰苯酮和各种苯甲酰氯进行的分子内ipso取代反应在制备5-羟基-4′-烷基黄酮方面是有效的。
• 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。
• Process for the preparation of flavone derivatives
  申请人：——

  公开号：US20040059100A1

  公开（公告）日：2004-03-25

  The invention relates to a process for the preparation of flavone derivatives in which a 2-hydroxyacetophenone compound is metallated using a lithium compound at low temperatures and subsequently reacted with a keto compound, and where the ratio of the molar equivalents of lithium compound to the 2-hydroxyacetophenone compound functional groups to be metallated is from 1 to 1.2. The resultant &bgr;-diketone compound is subsequently cyclised with warming in an acidic medium.

  本发明涉及一种制备黄酮衍生物的方法，其中使用锂化合物在低温下对2-羟基苯乙酮化合物进行金属化，然后与酮化合物反应，所述锂化合物的摩尔当量与要金属化的2-羟基苯乙酮化合物的官能团的比例为1至1.2。随后，在酸性介质中加热使所得的β-二酮化合物环化。
• Synthesis and inhibitory activity against COX-2 catalyzed prostaglandin production of chrysin derivatives
  作者：Tran Thanh Dao、Yeon Sook Chi、Jeongsoo Kim、Hyun Pyo Kim、Sanghee Kim、Haeil Park

  DOI：10.1016/j.bmcl.2003.12.087

  日期：2004.3

  A series of chrysin derivatives were prepared and evaluated for their inhibitory activities of cyclooxygenase-2 catalyzed prostaglandin production. Chrysin derivatives were prepared from 2-hydroxyacetophenone, 2,4-dihydroxyacetophenone and 2,6-dihydroxyacetophenone in 2 to 4 steps, respectively. Methxoylated chrysin derivatives were converted to the corresponding hydroxylated chrysin derivatives by the reaction with BBr3 in good yields. The inhibitory activity of the chrysin derivatives against prostaglandin production from lipopolysaccharide-treated RAW 264.7 cells was measured. We found that chrysin derivatives with 3',4'-dichloro substituents (5e, 6e and 7e) exhibited good inhibitory activity of prostaglandin production. (C) 2004 Elsevier Ltd. All rights reserved.
• 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.