(±)-5,7-dihydroxy-4-(4-methoxyphenyl)-3,4-dihydrocoumarin | 196817-57-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: (±)-5,7-dihydroxy-4-(4-methoxyphenyl)-3,4-dihydrocoumarin
• 英文别名: 5,7-dihydroxy-4-(4-methyoxyphenyl)-3,4-dihydrocoumarin；5,7-dihydroxy-4-(4-methoxyphenyl)-3,4-dihydrocoumarin；5,7-dihydroxy-4-(4-methoxyphenyl)-chroman-2-one；5,7-dihydroxy-4-(4-methoxyphenyl)chroman-2-one；4-(4-Methoxyphenyl)-5,7-dihydroxychroman-2-one；5,7-dihydroxy-4-(4-methoxyphenyl)-3,4-dihydrochromen-2-one
• CAS: 196817-57-9
• 化学式: C₁₆H₁₄O₅
• 分子量: 286.284
• InChiKey: OKBWVJGQTFYYQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2E)-3-(4-甲氧基苯基)丙烯酰氯 、 (±)-5,7-dihydroxy-4-(4-methoxyphenyl)-3,4-dihydrocoumarin 在 montmorillonite K-10 作用下， 以 硝基苯 为溶剂， 反应 12.0h， 以1.9 g的产率得到9-hydroxy-4,8-di(4-methoxyphenyl)-dichroman-2,6-dione
  参考文献：
  名称：

  An Efficient Synthesis of Neoflavonoid Antioxidants Based on Montmorillonite K-10 Catalysis

  摘要：

  描述了一种基于高产量的蒙脱石K-10催化的内酯环形成环化过程的合成新黄酮类化合物的新方法。通过制备取代的4-苯基新黄酮1-8，展示了该方法的应用价值。评估了这些物质的自由基清除特性。观察到模拟七叶亭类抗氧化剂的新黄酮1和5能清除羟自由基。

  DOI：

  10.1055/s-2001-18436
• 作为产物：
  描述：

  反式-4-甲氧基肉桂酸 在 氯化亚砜 、 montmorillonite K-10 作用下， 以 二氯甲烷 、 硝基苯 为溶剂， 反应 15.0h， 生成 (±)-5,7-dihydroxy-4-(4-methoxyphenyl)-3,4-dihydrocoumarin
  参考文献：
  名称：

  An Efficient Synthesis of Neoflavonoid Antioxidants Based on Montmorillonite K-10 Catalysis

  摘要：

  描述了一种基于高产量的蒙脱石K-10催化的内酯环形成环化过程的合成新黄酮类化合物的新方法。通过制备取代的4-苯基新黄酮1-8，展示了该方法的应用价值。评估了这些物质的自由基清除特性。观察到模拟七叶亭类抗氧化剂的新黄酮1和5能清除羟自由基。

  DOI：

  10.1055/s-2001-18436

文献信息

• Synthesis and biological evaluation of novel neoflavonoid derivatives as potential antidiabetic agents
  作者：Bing Wang、Na Li、Teng Liu、Jie Sun、Xiaojing Wang

  DOI：10.1039/c7ra06457h

  日期：——

  Various substituted neoflavonoid derivatives were synthesized using sulfated montmorillonite K-10 as a catalyst. This method is environmental friendly, sustainable and economical, convenient in isolation and purification processes, with little byproducts, using earth-abundant catalysts and has relatively high yield. Those neoflavonoid derivatives were screened for antioxidant, a-glucosidase inhibitory

  使用硫酸化的蒙脱石K-10作为催化剂合成了各种取代的新类黄酮衍生物。该方法是环境友好的，可持续的和经济的，使用丰富的地球催化剂，在分离和纯化过程中方便，副产物少，副产物少。筛选那些新类黄酮衍生物的抗氧化剂，α-葡萄糖苷酶抑制作用，醛糖还原酶2（ALR2）抑制作用和晚期糖基化终产物形成抑制作用。大多数化合物显示出显着的抗氧化剂和先进的糖基化终产物（AGE）形成抑制活性。有趣的是，在30种化合物中，8k和8l被发现比标准药物槲皮素具有更高的ALR2抑制活性。药理研究表明，具有相邻7,8-二羟基基团的新黄酮类化合物在抑制ALR2方面更有效。抗糖尿病活性研究表明，化合物8l和8m在体内与标准药物glibenclamide等效。总之，目标化合物81提供了用于开发糖尿病和糖尿病并发症的治疗剂或预防剂的潜在药物设计概念。
• Uncatalyzed Reaction of Phenols and Naphthols with Methyl Cinnamates. A Simple Synthesis of 4-Arylchroman-2-ones and 1-Arylbenzo[f]chroman-3-ones
  作者：Giovanna Speranza、Antonella Di Meo、Simona Zanzola、Gabriele Fontana、Paolo Manitto

  DOI：10.1055/s-1997-1293

  日期：1997.8

  4-Arylchroman-2-ones and 1-arylbenzo[f]chroman-3-ones can be prepared in moderate to good yields by reaction of phenols or β-naphthols with p-substituted methyl cinnamates in o-xylene under reflux.

  苯酚或δ-萘酚与对取代的肉桂酸甲酯在邻二甲苯中在回流条件下发生反应，可制备 4-芳基苯并[f]色满-2-酮和 1-芳基苯并[f]色满-3-酮，收率中等至良好。
• Synthesis and Hydroxyl Radical Scavenging Activity of 4-Aryl-3,4-Dihydrocoumarins
  作者：Na Li、Bing Wang、Jing-yong Sun、Xiao-jing Wang、Jie Sun

  DOI：10.1007/s10600-017-2141-x

  日期：2017.9

  Twelve 4-aryl-3,4-dihydrocoumarins were synthesized by the condensation of phenols with the corresponding substituted cinnamic acids in the presence of nitrobenzene and sulfated montmorillonite K-10. This method displayed the property of green chemistry with respect of reuse of the catalyst. These compounds were evaluated for hydroxyl radical scavenging activity in vitro. Results showed that compounds with 7,8-dihydroxy groups had relatively strong hydroxyl radical scavenging activity.

  在硝基苯和硫酸化蒙脱石 K-10 的存在下，通过苯酚与相应的取代肉桂酸缩合，合成了 12 种 4-芳基-3,4-二氢香豆素。这种方法具有催化剂可重复使用的绿色化学特性。对这些化合物进行了体外羟基自由基清除活性评估。结果表明，带有 7,8- 二羟基的化合物具有相对较强的羟自由基清除活性。
• Synthesis and biological evaluation of 4-arylcoumarins as potential anti-Alzheimer’s disease agents
  作者：Yinling Yun、Jie Yang、Yuhang Miao、Xiaojing Wang、Jie Sun

  DOI：10.1016/j.bmcl.2019.126900

  日期：2020.2

  Alzheimer's disease (AD) is a progressive neurological degenerative disease that has complex pathogenesis. A variety of studies in humans indicate that several enzymes inhibitors can be useful in the treatment of AD, including acetylcholinesterase (AchE), butyrylcholinesterase (BuChE) and monoamine oxidase (MAO). Various substituted 4-arylcoumarin derivatives were synthesised, and their activity in vitro were investigated, including AChE/BuChE inhibitory activity, MAO inhibitory activity, and antioxidant activity. Most of the compounds were found to exhibit high inhibitory activity, and individual compounds have extremely excellent activities. Therefore 4-arylcoumarins provides an idea for drugs design for the development of therapeutic or preventive agents for AD.
• An efficient and fast synthesis of 4-aryl-3,4-dihydrocoumarins by (CF3SO3)3Y catalysis under microwave irradiation
  作者：Cláudio E. Rodrigues-Santos、Aurea Echevarria

  DOI：10.1016/j.tetlet.2007.04.144

  日期：2007.6

  A new and efficient synthesis of eleven 4-aryl-3,4-dihydrocoumarins, in which six are new compounds, was performed using (CF3SO3)(3)Y as catalyst under microwave irradiation. The target compounds were obtained in good yields (68-80%) and remarkable time (7-20 min) when compared to the literature reports (1-40 h). (c) 2007 Elsevier Ltd. All rights reserved.