2,3-bis(4-hydroxyphenyl)-9H-xanthen-9-one | 1011792-21-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2,3-bis(4-hydroxyphenyl)-9H-xanthen-9-one
• 英文别名: 2,3-Bis(4-hydroxyphenyl)xanthen-9-one
• CAS: 1011792-21-4
• 化学式: C₂₅H₁₆O₄
• 分子量: 380.4
• InChiKey: UAZPKVGRYLIMBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,3-bis(4-methoxyphenyl)-9H-xanthen-9-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以94%的产率得到2,3-bis(4-hydroxyphenyl)-9H-xanthen-9-one
  参考文献：
  名称：

  合成羟基化 2,3-二芳基氧杂蒽的新途径

  摘要：

  描述了一种合成羟基化 2,3-二芳基氧杂蒽酮的新型、有效和通用的路线。该合成的关键中间体 3-Bromo-2-styrylchromone 是通过适当的 2'-肉桂酰氧基苯乙酮的 Baker-Venkataraman 重排，然后与苯-基三甲基三溴化铵进行一锅反应获得的。这些溴色酮与取代苯乙烯的 Heck 反应生成甲氧基化的 2,3-二芳基氧杂蒽酮。用 BBr 3 裂解甲基得到所需的羟基化 2,3-二芳基氧杂蒽酮。

  DOI：

  10.1055/s-2007-990900

文献信息

• Efficient Syntheses of New Polyhydroxylated 2,3-Diaryl-9<i>H</i>-xanthen-9-ones
  作者：Clementina M. M. Santos、Artur M. S. Silva、José A. S. Cavaleiro

  DOI：10.1002/ejoc.200900026

  日期：2009.6

  between 3-bromo-2-methyl-4H-chromen-4-one and benzaldehydes, or through Baker–Venkataraman rearrangements of 2-acetylphenyl cinnamates, followed by one-pot bromination/cyclisation with phenyltrimethylammonium tribromide. The 2,3-diaryl-9H-xanthene-9-ones were obtained in one-pot transformations involving Heck reactions between (E)-3-bromo-2-styryl-4H-chromen-4-ones and styrenes, followed by electrocyclisation

  已经通过两种不同的方法合成了大量羟基化的 2,3-二芳基-9H-xanthen-9-ones，从 3-bromo-2-methyl-4H-chromen-4-one 或 (E)- 3-bromo-2-styryl-4H-chromen-4-ones。前一种方法涉及 3-bromo-2-methyl-4H-chromen-4-one 和苯乙烯之间的 Heck 反应，导致 (E)-2-methyl-3-styryl-4H-chromen-4-ones; 这些与苯甲醛缩合得到 (E,E)-2,3-distyryl-4H-chromen-4-ones，这导致所需的 2,3-diaryl-9H-xanthen-9-ones 在 1,2 中回流,4-三氯苯。3-Bromo-2-styryl-4H-chromen-4-ones 是通过 3-bromo-2-methyl-4H-chromen-4-one 和苯甲醛之间的羟醛缩合获得的，或者通过
• A Novel and Efficient Route for the Synthesis of Hydroxylated 2,3-Diarylxanthones
  作者：Artur Silva、Clementina Santos、José Cavaleiro

  DOI：10.1055/s-2007-990900

  日期：——

  A novel, efficient and general route for the synthesis of hydroxylated 2,3-diarylxanthones is described. 3-Bromo-2-styrylchromone, the key intermediate of this synthesis, is obtained by a Baker-Venkataraman rearrangement of the appropriate 2′-cinnamoyloxyacetophenone, followed by a one-pot reaction with phen-yltrimethylammonium tribromide. The Heck reaction of these bromochromones with substituted

  描述了一种合成羟基化 2,3-二芳基氧杂蒽酮的新型、有效和通用的路线。该合成的关键中间体 3-Bromo-2-styrylchromone 是通过适当的 2'-肉桂酰氧基苯乙酮的 Baker-Venkataraman 重排，然后与苯-基三甲基三溴化铵进行一锅反应获得的。这些溴色酮与取代苯乙烯的 Heck 反应生成甲氧基化的 2,3-二芳基氧杂蒽酮。用 BBr 3 裂解甲基得到所需的羟基化 2,3-二芳基氧杂蒽酮。
• 2,3-Diarylxanthones as strong scavengers of reactive oxygen and nitrogen species: A structure–activity relationship study
  作者：Clementina M.M. Santos、Marisa Freitas、Daniela Ribeiro、Ana Gomes、Artur M.S. Silva、José A.S. Cavaleiro、Eduarda Fernandes

  DOI：10.1016/j.bmc.2010.07.044

  日期：2010.9

  Xanthones are a class of oxygen-containing heterocyclic compounds widely distributed in nature. The natural derivatives can present different substitutions in the xanthone core that include hydroxyl, methoxyl, prenyl and glycosyl groups. The inclusion of aryl groups has only been reported for a few synthetic derivatives, the 2,3-diaryl moiety being recently introduced by our group. Xanthones are endowed with a broad spectrum of biological activities, many of them related to their antioxidant ability, including the scavenging of reactive oxygen species (ROS) and reactive nitrogen species (RNS), as well as metal chelating effects. Considering the interesting and promising antioxidant activities present in compounds derived from the xanthone core, the main goal of this work was to evaluate the scavenging activity of the new 2,3-diarylxanthones for ROS, including superoxide radical (O-2(center dot-)), hydrogen peroxide (H2O2), singlet oxygen (O-1(2)), peroxyl radical (ROO center dot) and hypochlorous acid (HOCl), and RNS, including nitric oxide ((NO)-N-center dot) and peroxynitrite anion (ONOO center dot). The obtained results revealed that the tested 2,3-diarylxanthones are endowed with outstanding ROS and RNS scavenging properties, considering the nanomolar to micromolar range of the IC50 values found. The xanthones with two catechol rings were the most potent scavengers of all tested ROS and RNS. In conclusion, the new 2,3-diarylxanthones are promising molecules to be used for their potential antioxidant properties. (C) 2010 Elsevier Ltd. All rights reserved.