6-allyl-5-hydroxy-7-methoxy-2-phenylchroman-4-one | 1220680-32-9

• 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: 6-allyl-5-hydroxy-7-methoxy-2-phenylchroman-4-one
• 英文别名: 5-hydroxy-7-methoxy-6-(prop-2-enyl)flavanone；5-hydroxy-7-methoxy-2-phenyl-6-prop-2-enyl-2,3-dihydrochromen-4-one
• CAS: 1220680-32-9
• 化学式: C₁₉H₁₈O₄
• 分子量: 310.35
• InChiKey: GPZBTGQYJHAVKB-UHFFFAOYSA-N

物化性质

• 熔点：
  86-87 °C
• 沸点：
  518.3±50.0 °C(predicted)
• 密度：
  1.217±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-allyl-5-hydroxy-7-methoxy-2-phenylchroman-4-one 、 异丁烯 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到5-Hydroxy-7-methoxy-6-prenyl-flavanon
  参考文献：
  名称：

  Efficient microwave-assisted prenylation of pinostrobin and biological evaluation of its derivatives as antitumor agents

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2010.02.068
• 作为产物：
  描述：

  7-methoxy-5-(prop-2-enyloxy)flavanone 以 氯仿 为溶剂， 反应 2.0h， 以70%的产率得到6-allyl-5-hydroxy-7-methoxy-2-phenylchroman-4-one
  参考文献：
  名称：

  Efficient microwave-assisted prenylation of pinostrobin and biological evaluation of its derivatives as antitumor agents

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2010.02.068

文献信息

• Ethylation And Allylation Reactions of Pinostrobin from the Rhizome of Kaempferia pandurata
  作者：S. D. Marliyana、M. Firdaus、M. W. Wartono、U. W. Apriani、D. I. Utami

  DOI：10.1007/s10600-023-04197-z

  日期：2023.11
• 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.