(E)-1-(3-bromo-2-hydroxyl-4,6-dimethoxyphenyl)-3-(4-chlorophenyl)prop-2-en-1-one | 861137-52-2

• 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-hydroxyl-4,6-dimethoxyphenyl)-3-(4-chlorophenyl)prop-2-en-1-one
• 英文别名: (E)-1-(3-bromo-2-hydroxy-4,6-dimethoxyphenyl)-3-(4-chlorophenyl)prop-2-en-1-one
• CAS: 861137-52-2
• 化学式: C₁₇H₁₄BrClO₄
• 分子量: 397.653
• InChiKey: QWOMWULHOKUELE-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (E)-3-(4-chlorophenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)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90%的产率得到(E)-1-(3-bromo-2-hydroxyl-4,6-dimethoxyphenyl)-3-(4-chlorophenyl)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

• Synthesis and biological evaluation of novel series of chalcone derivatives as inhibitors of cyclooxygenase and LPS-induced TNF-α with potent antioxidant properties
  作者：Babasaheb P. Bandgar、Baliram S. Hote、Nagesh A. Dhole、Rajesh N. Gacche

  DOI：10.1007/s00044-011-9746-6

  日期：2012.9

  Novel series of chalcones were synthesized and were evaluated as possible anti-inflammatory agents targeting the cyclooxygenase-1 and 2 (COX-1 and 2), beta-glucuronidase, trypsin, and TNF-alpha. Amongst the tested chalcones the compound 4k was found to be most effective inhibitor of TNF-alpha exhibiting 85% inhibition activity (IC50 = 0.1 mu M). The compounds 4a, 4f, 4l, and 4m were found to inhibit the COX-1 activity in as a range of 79.95-68.47% and COX-2 inhibition ranging 84.45-74.77%. The compounds 4l (81.71%) and 4f (72.10%) were found to be excellent inhibitors of trypsin and beta-glucuronidase, respectively.
• 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.