(E)-1-(3-bromo-2-hydroxy-4,6-dimethoxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one | 1394173-48-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-1-(3-bromo-2-hydroxy-4,6-dimethoxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
• CAS: 1394173-48-8
• 化学式: C₂₀H₂₁BrO₇
• 分子量: 453.287
• InChiKey: FNNZAOQRPPCQPL-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one 在 溴化二甲基溴化锍 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到(E)-1-(3-bromo-2-hydroxy-4,6-dimethoxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2012.06.122

文献信息

• 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.