8-bromo-4',5,7-trimethoxyflavone | 35095-45-5

• 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: 8-bromo-4',5,7-trimethoxyflavone
• 英文别名: 8-Brom-5,7,4'-trimethoxy-flavon；8-Bromo-5,7-dimethoxy-2-(4-methoxyphenyl)chromen-4-one
• CAS: 35095-45-5
• 化学式: C₁₈H₁₅BrO₅
• 分子量: 391.218
• InChiKey: SKEYHWIWSQXUEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  8-bromo-4',5,7-trimethoxyflavone 在 四(三苯基膦)钯 、 三溴化硼 、 caesium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 podocarflavone A
  参考文献：
  名称：

  The first synthesis of podocarflavone A and its analogs and evaluation of their antimycobacterial potential against Mycobacterium tuberculosis with the support of virtual screening

  摘要：

  DOI：

  10.1080/14786419.2021.1893317
• 作为产物：
  描述：

  (E)-1-(2-羟基-4,6-二甲氧基苯基)-3-(4-甲氧基苯基)-2-丙烯-1-酮 在 氢氧化钾 、 溴化铵 、 双氧水 、 vanadia 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 8-bromo-4',5,7-trimethoxyflavone
  参考文献：
  名称：

  A highly efficient and environmentally benign synthesis of 6,8-dibromoflavones, 8-bromoflavones, 5,7-dibromoaurones and 7-bromoaurones

  摘要：

  Various ring substituted 6,8-dibromoflavones (3a-e) as well as 8-bromoflavolics (3f-j) can be synthesized easily from the corresponding 2'-hydroxychalcones (1a-j) in good yields and in two steps under environmentally benign reaction conditions. This can be achieved by bromination with concomitant cyclization by using a combination of vanadium pentoxide, hydrogen peroxide and ammonium bromide in dichloromethane-water at 0-5 degrees C, followed by dehydrobromination of the brominated products 2a-j using 0.2 M ethanolic KOH Solution at ice-bath temperature. On the other hand, various 5,7-dibromoaurones and 7-bromoaurone derivatives 6a-c can be obtained, exclusively, from the corresponding 2'-acetoxychalcones (4a-c) in good yields and in two steps by turing the reaction conditions. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.05.102

文献信息

• Efficient synthesis of polyoxygenated flavones from naturally occurring flavanones
  作者：Paolo Bovicelli、Vittoria D'Angelo、Daniela Collalto、Antonio Verzina、Nicola D'Antona、Daniela Lambusta

  DOI：10.1211/jpp.59.12.0012

  日期：2010.2.18

  of the increasing interest in these molecules, methods for their synthesis and structural modification are of great importance; studies on the biological activities of many of these compounds are insufficient because of their scarcity and/or high cost. We have developed an expeditious synthesis of polyoxygenated flavones, starting from available and inexpensive flavanones, using a bromination-methoxylation

  类黄酮是人类饮食的成分（它们存在于许多饮料和食品中），在生物体中，它们具有多种生物功能，包括抗氧化剂的功能。由于对这些分子的兴趣日益增加，其合成和结构修饰的方法非常重要。由于它们的稀缺性和/或成本高昂，因此对这些化合物中许多生物活性的研究还不够。我们已经开发了一种快速合成多氧合黄酮的方法，该方法从现有的廉价黄烷酮开始，采用溴化-甲氧基化方法。使用这种方法可以制备一系列否则无法获得的类黄酮。举例来说，3'-脱甲氧基苏达壳素
• Regioselective monobromination of (E)-1-(2′-hydroxy-4′,6′-dimethoxyphenyl)-3-aryl-2-propen-1-ones using bromodimethylsulfonium bromide and synthesis of 8-bromoflavones and 7-bromoaurones
  作者：Abu T. Khan、Abhik Choudhury、Shahzad Ali、Md. Musawwer Khan

  DOI：10.1016/j.tetlet.2012.06.122

  日期：2012.9

  A wide variety of monobrominated compounds 2a-I have been prepared in good yields from (E)-1-(2'-hydroxy-4',6'-dimethoxyphenyl)-3-aryl-2-propen-1-ones (1a-I) through regioselective ring bromination using 1.5 equiv of bromodimethylsulfonium bromide (BDMS) at room temperature. Similarly, some of the 2'-hydroxychalcones can be converted directly into tribromides 3 or dibromides 4 by employing 4.0 equiv of BDMS under different reaction conditions which in turn can be transformed into 8-bromoflavones and 7-bromoaurones on treatment with 0.2 M ethanolic KOH solution. Mild reaction conditions, good yields and no chromatographic separation are some of the salient features of the present protocol. (C) 2012 Elsevier Ltd. All rights reserved.
• UENG, TSONG;CHEN, FA-CHING, J. CHIN. CHEM. SOC., 1982, 29, N 2, 99-105
  作者：UENG, TSONG、CHEN, FA-CHING

  DOI：——

  日期：——
• ROBUSTAFLAVONE, INTERMEDIATES AND ANALOGUES AND METHOD FOR PREPARATION THEREOF
  申请人：Advanced Life Sciences, Inc.

  公开号：EP1007528B1

  公开（公告）日：2003-11-26
• US6225481B1
  申请人：——

  公开号：US6225481B1

  公开（公告）日：2001-05-01