6-hydroxy-4-(3,4-dimethoxyphenyl)-3,4-dihydrobenzopyran-2-one | 1259079-13-4

• 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: 6-hydroxy-4-(3,4-dimethoxyphenyl)-3,4-dihydrobenzopyran-2-one
• 英文别名: (+/-)-6-Hydroxy-4-(3,4-dimethoxyphenyl)-3,4-dihydrocoumarin；4-(3,4-dimethoxyphenyl)-6-hydroxy-3,4-dihydrochromen-2-one
• CAS: 1259079-13-4
• 化学式: C₁₇H₁₆O₅
• 分子量: 300.311
• InChiKey: KHSMGTGMAKODQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,4-二甲氧基苯甲醛 在 哌啶 、 吡啶 作用下， 以 硝基苯 为溶剂， 反应 8.0h， 生成 6-hydroxy-4-(3,4-dimethoxyphenyl)-3,4-dihydrobenzopyran-2-one
  参考文献：
  名称：

  新型新黄酮衍生物作为潜在的抗糖尿病药的合成和生物学评估†

  摘要：

  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。

  DOI：

  10.1039/c7ra06457h

文献信息

• Synthesis and antimicrobial activities of 4-aryl-3,4-dihydrocoumarins and 4-arylcoumarins
  作者：Jie Sun、Wei-Xian Ding、Xiao-Ping Hong、Ke-Yun Zhang、Yong Zou

  DOI：10.1007/s10600-012-0149-9

  日期：2012.3

  A new series of 4-aryl-3,4-dihydrocoumarins and 4-arylcoumarins were synthesized by the reaction of substituted cinnamic acids and 3-arylpropiolic acid with the corresponding phenols. These compounds were evaluated for antibacterial activity in vitro. The synthesized compounds displayed different degrees of antimicrobial activity against Staphylococcus aureus, Escherichia coli, and Bacillus dysenteriae, and Candida albicans (a fungus). Compounds with catechol moieties and 7,8-substituted dihydroxyls in the A ring were the most active antimicrobial agents.

  通过取代肉桂酸和3-芳基炔酸与相应的酚反应，合成了一系列4-芳基-3,4-二氢香豆素和4-芳基香豆素。这些化合物在体外评估了抗菌活性。合成的化合物对金黄色葡萄球菌、大肠杆菌、痢疾杆菌和白色念珠菌（真菌）表现出不同程度的抗微生物活性。具有羟基苯环和7,8-取代二羟基的A环化合物是最活跃的抗微生物剂。
• Synthesis and NMR of 4-Aryl-3,4-dihydrocoumarins and 4-Arylcoumarins
  作者：Jie Sun、Yanfeng Wang

  DOI：10.14233/ajchem.2014.17751

  日期：——

  This paper described the synthesis and 1H and 13C NMR chemical shifts of a series of 4-aryl-3,4-dihydrocoumarin and 4-arylcoumarin derivatives based on a combination of 1H and 13C NMR, HSQC and HMBC experiments.

  本文结合 1H 和 13C NMR、HSQC 和 HMBC 实验，描述了一系列 4-芳基-3,4-二氢香豆素和 4-芳基香豆素衍生物的合成以及 1H 和 13C NMR 化学位移。
• 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.
• Molecular iodine catalyst promoted synthesis of chromans and 4-aryl-3,4-dihydrobenzopyran-2-ones via [3+3] cyclocoupling
  作者：Mayuri M. Naik、Durga P. Kamat、Santosh G. Tilve、Vijayendra P. Kamat

  DOI：10.1016/j.tet.2014.05.093

  日期：2014.8

  Molecular iodine as an inexpensive catalyst is described in the construction of 2-substituted or 2,2-disubstituted chromans and 4-aryl-3,4-dihydrobenzopyran-2-ones via [3+3] cyclocoupling. For the synthesis of chromans, phenols and allylic alcohols were refluxed in chloroform in presence of 20 mol % I-2 while [3+3] cyclocoupling of phenols and cinnamic acids proceeded to give 4-aryl-3,4-dihydrobenzopyran-2-ones using 30 mol % I-2. Later reaction occurs via a tandem hydroarylation-esterification process at 120-130 degrees C under solvent free conditions. Chromans were obtained in 20-92% yields and substituted 4-aryl-3,4-dihydrobenzopyran-2-ones were obtained in 5-85% yields. (C) 2014 Elsevier Ltd. All rights reserved.