5,7-dihydroxy-3-(3',5'-dihydroxyphenyl)coumarin | 1255948-02-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 5,7-dihydroxy-3-(3',5'-dihydroxyphenyl)coumarin
• 英文别名: 3-(3,5-Dihydroxyphenyl)-5,7-dihydroxychromen-2-one；3-(3,5-dihydroxyphenyl)-5,7-dihydroxychromen-2-one
• CAS: 1255948-02-7
• 化学式: C₁₅H₁₀O₆
• 分子量: 286.241
• InChiKey: NHTNTNOJCRKGIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 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：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5,7-diacetoxy-3-(3',5'-diacetoxyphenyl)coumarin 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 以94%的产率得到5,7-dihydroxy-3-(3',5'-dihydroxyphenyl)coumarin
  参考文献：
  名称：

  Hydroxyl Substitutional Effect on Selective Synthesis of cis, trans Stilbenes and 3-Arylcoumarins Through Perkin Condensation

  摘要：

  The substitutional effect in the selective synthesis of cis, trans stilbenes and 3-arylcoumarins has been described. The regio- and geometrical selectivity for synthesis of stilbene derivatives under the Perkin strategy strongly depends on the presence or absence of hydroxyl group as well as their positions in the phenyl ring. As a result, practical synthetic strategies were established for preparing various natural stilbenes including combretastatin A-4, pterostilbene, and resveratrol with satisfactory yields (49.2-63.7%).

  DOI：

  10.1080/00397911.2010.538889

文献信息

• Design, synthesis and antitumor activity of a series of novel coumarin–stilbenes hybrids, the 3-arylcoumarins
  作者：Chun Fen Xiao、Li Yang Tao、Hong Yi Sun、Wen Wei、Yu Chen、Li Wu Fu、Yong Zou

  DOI：10.1016/j.cclet.2010.04.034

  日期：2010.11

  A series of novel coumarin-stilbenes hybrids called 3-arylcoumarins were synthesized via Perkin reaction and evaluated as potential antitumor agents. The results showed that some compounds exhibited in vitro activity against KB, KV, MCF-7, MCF-7/ADR cell lines to some extent. Compound 3a showed remarkable effect against KB tumor cells with an IC50 value of 5.18 mu mol/L. (C) 2010 Yong Zou. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
• Hydroxyl Substitutional Effect on Selective Synthesis of <i>cis, trans</i> Stilbenes and 3-Arylcoumarins Through Perkin Condensation
  作者：Chun-Fen Xiao、Yong Zou、Jian-Li Du、Hong-Yi Sun、Xian-Ke Liu

  DOI：10.1080/00397911.2010.538889

  日期：2012.5.1

  The substitutional effect in the selective synthesis of cis, trans stilbenes and 3-arylcoumarins has been described. The regio- and geometrical selectivity for synthesis of stilbene derivatives under the Perkin strategy strongly depends on the presence or absence of hydroxyl group as well as their positions in the phenyl ring. As a result, practical synthetic strategies were established for preparing various natural stilbenes including combretastatin A-4, pterostilbene, and resveratrol with satisfactory yields (49.2-63.7%).