5-Hydroxy-7-methoxy-6-prenyl-flavanon | 59718-54-6

• 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: 5-Hydroxy-7-methoxy-6-prenyl-flavanon
• 英文别名: 5-hydroxy-7-methoxy-6-(3-methyl-but-2-enyl)flavanone；5-Hydroxy-7-methoxy-6-C-prenylflavanone；5-hydroxy-7-methoxy-6-(3-methylbut-2-enyl)-2-phenyl-2,3-dihydrochromen-4-one
• CAS: 59718-54-6
• 化学式: C₂₁H₂₂O₄
• 分子量: 338.403
• InChiKey: SIGVEYBZDIDQLH-UHFFFAOYSA-N

物化性质

• 熔点：
  90-91 °C(Solvent: Hexane; Ethyl acetate)
• 沸点：
  537.1±50.0 °C(predicted)
• 密度：
  1.182±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  松属素 在 氢氧化钾 、 18-冠醚-6 作用下， 以 甲醇 为溶剂， 反应 28.0h， 生成 5-Hydroxy-7-methoxy-6-prenyl-flavanon
  参考文献：
  名称：

  Variations in the Chemical Shift of the 5-Hydroxyl Proton of 7-O-Prenylated Flavanones

  摘要：

  DOI：

  10.3987/com-96-7415

文献信息

• Efficient microwave-assisted prenylation of pinostrobin and biological evaluation of its derivatives as antitumor agents
  作者：Hadi Poerwono、Shigeru Sasaki、Yoshiyuki Hattori、Kimio Higashiyama

  DOI：10.1016/j.bmcl.2010.02.068

  日期：2010.4

  Pinostrobin (5-hydroxy-7-methoxyflavanone) obtained in relatively large amounts from fingerroot (Boesenbergia pandurata) was converted to its C-6 and C-8 prenylated derivatives. The Mitsunobu reaction, europium(III)-catalyzed Claisen-Cope rearrangement, and Claisen reaction coupled with cross-metathesis were used as the key steps. Using a sealed-vessel microwave reactor, the Mitsunobu and Claisen/Cope reactions occurred smoothly with short reaction times and in satisfactory yields. The target compounds and five new intermediary substances showed cytotoxic activity toward SK-BR-3, MCF-7, PC-3, and Colo-320DM human tumor cell lines, and all of them had significantly lower IC50 (mu M) values than pinostrobin. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.
• Variations in the Chemical Shift of the 5-Hydroxyl Proton of 7-O-Prenylated Flavanones
  作者：Taro Nomura、Toshio Fukai

  DOI：10.3987/com-96-7415

  日期：——