6,8-dibromo-4',7-dimethoxyflavone | 38493-28-6

• 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: 6,8-dibromo-4',7-dimethoxyflavone
• 英文别名: 6,8-Dibrom-7,4'-dimethoxyflavon；6,8-dibromo-7-methoxy-2-(4-methoxy-phenyl)-chromen-4-one；6,8-Dibromo-7-methoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one；6,8-dibromo-7-methoxy-2-(4-methoxyphenyl)chromen-4-one
• CAS: 38493-28-6
• 化学式: C₁₇H₁₂Br₂O₄
• 分子量: 440.088
• InChiKey: GCBUQLQUKBDROP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,6,8-tribromo-4',7-dimethoxyflavanone 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 以84%的产率得到6,8-dibromo-4',7-dimethoxyflavone
  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

• A highly efficient and environmentally benign synthesis of 6,8-dibromoflavones, 8-bromoflavones, 5,7-dibromoaurones and 7-bromoaurones
  作者：Abu T. Khan、Papori Goswami

  DOI：10.1016/j.tetlet.2005.05.102

  日期：2005.7

  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.