5-羟基-7-甲氧基-8-(3-甲基丁-2-烯基)-2-苯基-2,3-二氢色烯-4-酮 | 75291-75-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 5-羟基-7-甲氧基-8-(3-甲基丁-2-烯基)-2-苯基-2,3-二氢色烯-4-酮
• 英文名称: 5-hydroxy-7-methoxy-3-C-prenylflavone
• 英文别名: 5-hydroxyisoderricin；8-prenylpinostrobin；7-methylglabranine；7-methylglabranin；7,7-methylglabranin；5-Hydroxy-7-methoxy-8-prenyl-flavanon；Tephrinone；5-hydroxy-7-methoxy-8-(3-methylbut-2-enyl)-2-phenyl-2,3-dihydrochromen-4-one
• CAS: 75291-75-7
• 化学式: C₂₁H₂₂O₄
• 分子量: 338.403
• InChiKey: NISHDQWTPMJBJI-UHFFFAOYSA-N

物化性质

• 熔点：
  112-113 °C(Solv: hexane (110-54-3))
• 沸点：
  537.1±50.0 °C(Predicted)
• 密度：
  1.182±0.06 g/cm3(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

• 作为反应物：
  描述：

  5-羟基-7-甲氧基-8-(3-甲基丁-2-烯基)-2-苯基-2,3-二氢色烯-4-酮 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 2-hydroxy-4,6-dimethoxy-3-prenylacetophenone
  参考文献：
  名称：

  A new prenylated flavanone from Tephrosia villosa

  摘要：

  DOI：

  10.1016/0031-9422(80)83111-6
• 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-羟基-7-甲氧基-8-(3-甲基丁-2-烯基)-2-苯基-2,3-二氢色烯-4-酮
  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

• Antimicrobial agents from higher plants: Prenylated flavonoids and other phenols from Glycyrrhiza lepidota
  作者：Lester A. Mitscher、G.S. Raghav Rao、Ish Khanna、Tarik Veysoglu、Steven Drake

  DOI：10.1016/0031-9422(83)83049-0

  日期：1983.1

  of extracts of American licorice, Glycyrrhiza lepidota (Leguminosae), resulted in identification of the known bibenzyl, 3,5-dihydroxy-4-(3-methyl-2-butenyl)-bibenzyl, and the known flavanones, glabranin and pinocembrin, as well as the isolation and structure determination of the new flavonol, glepidotin A and the new dihydroflavonol, glepidotin B as antimicrobial agents.

  摘要 对美国甘草、甘草 (豆科) 提取物进行生物测定定向分馏，鉴定了已知的联苄、3,5-二羟基-4-(3-甲基-2-丁烯基)-联苄和已知的黄烷酮、光甘草素和松香素，以及作为抗菌剂的新型黄酮醇格列吡汀 A 和新型二氢黄酮醇格列吡汀 B 的分离和结构测定。
• Hossain, M. Amzad, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 4, p. 431 - 433
  作者：Hossain, M. Amzad

  DOI：——

  日期：——
• 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.
• Suarez, L. E. Cuca; Monache, F. Delle; Bettolo, G. B. Marini, Farmaco, Edizione Scientifica, 1980, vol. 35, # 9, p. 796 - 800
  作者：Suarez, L. E. Cuca、Monache, F. Delle、Bettolo, G. B. Marini、Menichini, F.

  DOI：——

  日期：——