2,6-Dibenzoyloxy-acetophenon | 40296-16-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 2,6-Dibenzoyloxy-acetophenon
• 英文别名: 2-Acetyl-3-(benzoyloxy)phenyl benzoate；(2-acetyl-3-benzoyloxyphenyl) benzoate
• CAS: 40296-16-0
• 化学式: C₂₂H₁₆O₅
• 分子量: 360.366
• InChiKey: QYFZYFIBENTTAX-UHFFFAOYSA-N

物化性质

• 沸点：
  572.2±45.0 °C(Predicted)
• 密度：
  1.252±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,6-Dibenzoyloxy-acetophenon 在 potassium carbonate 、 potassium iodide 作用下， 以 吡啶 、 丙酮 为溶剂， 反应 14.0h， 生成 3-benzoyl-5-benzyloxyflavone
  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：

  8-乙酰基-7-羟基-4-甲基-2H-1-苯并吡喃-2-酮 在 吡啶 、 sodium hydroxide 作用下， 生成 2,6-Dibenzoyloxy-acetophenon
  参考文献：
  名称：

  429.尝试合成5：6-二羟基黄酮（primetin）

  摘要：

  DOI：

  10.1039/jr9340001953

文献信息

• Baker-Venkataraman Rearrangement Under Microwave Irradiation: A New Strategy for the Synthesis of 3-Aroyl-5-hydroxyflavones
  作者：Artur Silva、Diana Pinto、José Cavaleiro

  DOI：10.1055/s-2007-984525

  日期：2007.7

  Microwave irradiation selectively induces the Baker-Venkataraman rearrangement of 2′,6′-diaroyloxyacetophenones to give 3-aroyl-5-hydroxyflavones, in a very short reaction time. ­Under classical heating conditions these reactions afforded 5-hydroxyflavones as byproducts.

  微波辐照能在极短的反应时间内选择性地诱导 2′,6′-二芳酰氧基苯乙酮发生贝克-文卡塔拉曼重排反应，生成 3-芳酰基-5-羟基黄酮。在传统的加热条件下，这些反应的副产物为 5-羟基黄酮。
• Limaye; Gangal, Rasayanam, 1936, vol. 1, p. 64,66
  作者：Limaye、Gangal

  DOI：——

  日期：——
• 344. Chromones of the naphthalene series. Part I. Transformation of o-aroyloxyacetoarones into o-hydroxydiaroylmethanes
  作者：V. V. Virkar、T. S. Wheeler

  DOI：10.1039/jr9390001679

  日期：——
• Iyer; Venkataraman, Proceedings - Indian Academy of Sciences, Section A, 1953, vol. 37, p. 629,636
  作者：Iyer、Venkataraman

  DOI：——

  日期：——
• 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.