3-benzoyl-2-phenyl-4H-1-benzopyran-4-one | 5453-03-2

• 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: 3-benzoyl-2-phenyl-4H-1-benzopyran-4-one
• 英文别名: 3-benzoyl-2-phenylchromone；3-benzoyl-2-phenyl-4H-chromen-4-one；3-Benzoyl-2-phenylchromen-4-one
• CAS: 5453-03-2
• 化学式: C₂₂H₁₄O₃
• 分子量: 326.351
• InChiKey: UGWVLVPQDKBUMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  25
• 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：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2914399090

反应信息

• 作为反应物：
  描述：

  3-benzoyl-2-phenyl-4H-1-benzopyran-4-one 在 碳酸氢钠 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以85%的产率得到黄酮
  参考文献：
  名称：

  An efficient one-pot synthesis of flavones

  摘要：

  Flavones were prepared using a one-pot procedure starting from the corresponding 2'-hydroxyacetophenones. The latter were treated with 3 equiv of aroyl chloride in wet K2CO3/acetone (1% w/w water) to afford a good yield of flavone and a smaller amount of 3-aroylflavone. Evidence was obtained that the reaction proceeds via a triketone intermediate. When the reactants were heated in 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and pyridine, the 3-aroylflavone was obtained exclusively. Use of a stoichiometric amount of aroyl chloride afforded only the corresponding flavone. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.04.022
• 作为产物：
  描述：

  2-iodophenyl benzoate 在 镍 tris(dibenzylideneacetone)dipalladium (0) 、 三苯胂 、 氢气 作用下， 反应 51.5h， 生成 3-benzoyl-2-phenyl-4H-1-benzopyran-4-one
  参考文献：
  名称：

  Ellemose, Steen; Kure, Niels; Torsell, Kurt B. G., Acta Chemica Scandinavica, 1995, vol. 49, # 7, p. 524 - 529

  摘要：

  DOI：

文献信息

• Synthesis and properties of 3-acyl-γ-pyrones, a novel class of flavones and chromones
  作者：A.K. Ganguly、S. Kaur、P.K. Mahata、D. Biswas、B.N. Pramanik、T.M. Chan

  DOI：10.1016/j.tetlet.2005.04.010

  日期：2005.6

  Using modified Baker–Venkataraman reaction a novel class of 3-acyl flavones and chromones have been synthesised. Reaction mechanism for their formation have been elucidated. The properties of 3-acyl flavonoids indicate them to be precursors for the synthesis of flavones.

  使用改良的Baker-Venkataraman反应，可以合成一类新型的3-酰基黄酮和色酮。已经阐明了其形成的反应机理。3-酰基类黄酮的性质表明它们是黄酮合成的前体。
• Synthesis of flavone-3-sulfonylureas
  作者：Werner Löwe、Norbert Matzanke

  DOI：10.1002/jhet.5570330364

  日期：1996.5

  The synthesis of new flavone-3-sulfonylurea derivatives is hereby described. The influence of a phenyl group in the 2-position and an acetate group in the 8-position at the chromone nucleus on the activity was studied. Only weak cytostatic activity of the new compounds was found.

  因此描述了新的黄酮-3-磺酰脲衍生物的合成。研究了色酮核中2-位的苯基和8位的乙酸酯基对活性的影响。仅发现新化合物的弱细胞抑制活性。
• A concise synthesis of 3-aroylflavones via Lewis base 9-azajulolidine-catalyzed tandem acyl transfer–cyclization
  作者：Masahito Yoshida、Koya Saito、Yuta Fujino、Takayuki Doi

  DOI：10.1039/c2cc37015h

  日期：——

  Lewis base-catalyzed tandem acyl transfer-cyclization of acylated o-alkynoylphenols leading to 3-aroylflavones was developed. 9-Azajulolidine smoothly promoted the reaction of the aroyl derivatives at ambient temperature, and the structure-diversed synthesis of 3-aroylflavones with distinct substituents was achieved in moderate to excellent yields.

  开发了路易斯碱催化导致3-芳基黄酮的酰化的邻炔基酚的串联酰基转移环化。9-氮杂唑烷在环境温度下平稳地促进了芳酰基衍生物的反应，并且以中等至优异的产率实现了具有不同取代基的3-芳酰基黄酮的结构多样的合成。
• Synthesis of 2-substituted 3-iodo-4H-chromen-4-ones
  作者：K. A. Myannik、V. N. Yarovenko、M. M. Krayushkin、K. S. Levchenko

  DOI：10.1007/s11172-014-0466-1

  日期：2014.2

  3-Iodochromones containing phenyl and furyl fragments at position 2 were synthesized by heterocyclization of β-ketoenamines.

  通过β-酮烯胺的杂环合成了位置 2 上含有苯基和呋喃基片段的 3-碘色酮。
• New Syntheses of 3-Aroylflavone Derivatives; Knoevenagel Condensation and Oxidation versus One-Pot Synthesis
  作者：Diana Pinto、Artur Silva、Patrícia Vaz、Djenisa Rocha、José Cavaleiro

  DOI：10.1055/s-0032-1317159

  日期：——

  syntheses of 3-aroylflavones have been established. In the first synthesis the use of microwave irradiation led to an improvement in the yields of both the Knoevenagel condensation of β-diketones with aldehydes to afford 3-aroylflavanones and of their oxidation to 3-aroylflavones. In the second and more general synthesis, a novel and efficient procedure for 3-aroylflavones involves a one-pot reaction between

  已经建立了 3-芳酰基黄酮的两种合成方法。在第一次合成中，微波辐射的使用导致 β-二酮与醛的 Knoevenagel 缩合得到 3-芳酰基黄烷酮以及它们氧化为 3-芳酰基黄酮的产率的提高。在第二个和更一般的合成中，3-芳酰基黄酮的新型有效程序涉及在双（三甲基甲硅烷基）氨基锂存在下 2'-羟基苯乙酮和芳酰氯之间的一锅反应。