4-chloro-2'-hydroxy-6'-methoxychalcone | 126494-89-1

• 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: 4-chloro-2'-hydroxy-6'-methoxychalcone
• 英文别名: (E)-3-(4-chlorophenyl)-1-(2-hydroxy-6-methoxyphenyl)prop-2-en-1-one
• CAS: 126494-89-1
• 化学式: C₁₆H₁₃ClO₃
• 分子量: 288.73
• InChiKey: UVLYOABANHYJFS-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-chloro-2'-hydroxy-6'-methoxychalcone 在 sodium carbonate 、 双氧水 作用下， 以 甲醇 、 水 为溶剂， 反应 24.5h， 以27%的产率得到2-(4-chlorophenyl)-3-hydroxy-5-methoxy-4H-chromen-4-one
  参考文献：
  名称：

  通过Algar-Flynn-Oyamada（AFO）反应合成5-取代的黄酮醇：机理上的意义

  摘要：

  本文中，我们报告了一种合成方法，该方法通过使用碳酸钠/过氧化氢，通过Algar-Flynn-Oyamada反应（AFO）对5-取代的黄酮醇进行了改进，具有中等至高收率的一系列5-取代的黄酮醇。阐明了AFO反应的机理。LCMS分析和原位1 H NMR分析表明，在碱性碱/过氧化物条件下，环氧化物参与了从查尔酮到黄酮醇和/或金酮的转化。

  DOI：

  10.1016/j.tet.2017.06.064
• 作为产物：
  描述：

  2,6-二羟基苯乙酮 在 氢氧化钾 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 生成 4-chloro-2'-hydroxy-6'-methoxychalcone
  参考文献：
  名称：

  Synthesis and inhibitory activity against COX-2 catalyzed prostaglandin production of chrysin derivatives

  摘要：

  A series of chrysin derivatives were prepared and evaluated for their inhibitory activities of cyclooxygenase-2 catalyzed prostaglandin production. Chrysin derivatives were prepared from 2-hydroxyacetophenone, 2,4-dihydroxyacetophenone and 2,6-dihydroxyacetophenone in 2 to 4 steps, respectively. Methxoylated chrysin derivatives were converted to the corresponding hydroxylated chrysin derivatives by the reaction with BBr3 in good yields. The inhibitory activity of the chrysin derivatives against prostaglandin production from lipopolysaccharide-treated RAW 264.7 cells was measured. We found that chrysin derivatives with 3',4'-dichloro substituents (5e, 6e and 7e) exhibited good inhibitory activity of prostaglandin production. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.087

文献信息

• Miles, Christopher O.; Main, Lyndsay; Nicholson, Brian K., Australian Journal of Chemistry, 1989, vol. 42, # 7, p. 1103 - 1114
  作者：Miles, Christopher O.、Main, Lyndsay、Nicholson, Brian K.

  DOI：——

  日期：——
• MILES, CHRISTOPHER O.;MAIN, LYNDSAY;NICHOLSON, BRIAN K., AUSTRAL. J. CHEM., 42,(1989) N, C. 1103-1113
  作者：MILES, CHRISTOPHER O.、MAIN, LYNDSAY、NICHOLSON, BRIAN K.

  DOI：——

  日期：——
• Synthesis and inhibitory activity against COX-2 catalyzed prostaglandin production of chrysin derivatives
  作者：Tran Thanh Dao、Yeon Sook Chi、Jeongsoo Kim、Hyun Pyo Kim、Sanghee Kim、Haeil Park

  DOI：10.1016/j.bmcl.2003.12.087

  日期：2004.3

  A series of chrysin derivatives were prepared and evaluated for their inhibitory activities of cyclooxygenase-2 catalyzed prostaglandin production. Chrysin derivatives were prepared from 2-hydroxyacetophenone, 2,4-dihydroxyacetophenone and 2,6-dihydroxyacetophenone in 2 to 4 steps, respectively. Methxoylated chrysin derivatives were converted to the corresponding hydroxylated chrysin derivatives by the reaction with BBr3 in good yields. The inhibitory activity of the chrysin derivatives against prostaglandin production from lipopolysaccharide-treated RAW 264.7 cells was measured. We found that chrysin derivatives with 3',4'-dichloro substituents (5e, 6e and 7e) exhibited good inhibitory activity of prostaglandin production. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis of 5-subsituted flavonols via the Algar-Flynn-Oyamada (AFO) reaction: The mechanistic implication
  作者：Xianyan Shen、Qiang Zhou、Wei Xiong、Wenchen Pu、Wei Zhang、Guolin Zhang、Chun Wang

  DOI：10.1016/j.tet.2017.06.064

  日期：2017.8

  Herein, we report a synthetic method with improved selectivity for 5-substituted flavonols via the Algar-Flynn-Oyamada reaction (AFO), by using of sodium carbonate/hydrogen peroxide A series of 5-substituted flavonols was obtained with moderate to high yields. The mechanism of the AFO reaction was elucidated. LCMS analysis and in situ 1H NMR analysis indicated that the epoxide was involved in the transformation

  本文中，我们报告了一种合成方法，该方法通过使用碳酸钠/过氧化氢，通过Algar-Flynn-Oyamada反应（AFO）对5-取代的黄酮醇进行了改进，具有中等至高收率的一系列5-取代的黄酮醇。阐明了AFO反应的机理。LCMS分析和原位1 H NMR分析表明，在碱性碱/过氧化物条件下，环氧化物参与了从查尔酮到黄酮醇和/或金酮的转化。