6-methoxy-3-(4-methoxybenzoyl)-2H-chromen-2-one | 1448688-04-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-methoxy-3-(4-methoxybenzoyl)-2H-chromen-2-one
• 英文别名: 6-methoxy-3-(4-methoxybenzoyl)coumarin
• CAS: 1448688-04-7
• 化学式: C₁₈H₁₄O₅
• 分子量: 310.306
• InChiKey: ZDQPHACKQDDXQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  65.74
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  6-methoxy-3-(4-methoxybenzoyl)-2H-chromen-2-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以65%的产率得到6-hydroxy-3-(4-hydroxybenzoyl)coumarin
  参考文献：
  名称：

  Synthesis and Electrochemical and Biological Studies of Novel Coumarin–Chalcone Hybrid Compounds

  摘要：

  A series of novel hydroxy-coumarin chalcone hybrid compounds 2a-i has been synthesized by employing a simple and efficient methodology. An electrochemical characterization using cyclic voltammetry and ESR spectroscopy were carried out to characterize the oxidation mechanism for the target compounds. The antioxidant capacity and reactivity were determined by ORAC and ESR assays, respectively. Biological assays were assessed to evaluate the cytotoxicity and cytoprotection capacity against ROS/RNS on BAEC. The results revealed that all tested compounds present ORAC values that are much higher than other well-known antioxidant compounds such as quercetin and catechin. Compound 2e showed the highest ORAC value (14.1) and also presented a low oxidation potential, good scavenging capacity against hydroxyl radicals, low cytotoxicity, and high cytoprotective activity.

  DOI：

  10.1021/jm400546y
• 作为产物：
  描述：

  2-羟基-5-甲氧基苯甲醛 、 3-(4-甲氧苯基)-3-氧代丙酸乙酯 在 哌啶 作用下， 以 乙醇 为溶剂， 以80%的产率得到6-methoxy-3-(4-methoxybenzoyl)-2H-chromen-2-one
  参考文献：
  名称：

  Synthesis and Electrochemical and Biological Studies of Novel Coumarin–Chalcone Hybrid Compounds

  摘要：

  A series of novel hydroxy-coumarin chalcone hybrid compounds 2a-i has been synthesized by employing a simple and efficient methodology. An electrochemical characterization using cyclic voltammetry and ESR spectroscopy were carried out to characterize the oxidation mechanism for the target compounds. The antioxidant capacity and reactivity were determined by ORAC and ESR assays, respectively. Biological assays were assessed to evaluate the cytotoxicity and cytoprotection capacity against ROS/RNS on BAEC. The results revealed that all tested compounds present ORAC values that are much higher than other well-known antioxidant compounds such as quercetin and catechin. Compound 2e showed the highest ORAC value (14.1) and also presented a low oxidation potential, good scavenging capacity against hydroxyl radicals, low cytotoxicity, and high cytoprotective activity.

  DOI：

  10.1021/jm400546y

文献信息

• Diastereoselective Synthesis of Rauhut–Currier-Type Adducts via an Unexpected α-Addition of α,β-Unsaturated γ-Butyrolactams to Coumarin Derivatives
  作者：Shu-Mei Yang、Ganapuram Madhusudhan Reddy、Meng-Hsien Liu、Tzu-Ping Wang、Jhen-Kuei Yu、Wenwei Lin

  DOI：10.1021/acs.joc.6b02526

  日期：2017.1.6

  highly diastereoselective direct Michael addition-isomerization sequence is presented for the efficient synthesis of Rauhut–Currier-type adducts. An unexpected α-addition of γ-butyrolactam onto the 3-acyl coumarin derivatives was observed rather than the γ-addition, which is more common. The adducts could further undergo hydrolysis/decarboxylation to generate the products which are equivalent to those

  为有效合成Rauhut-Currier型加合物，提出了一种新颖的碱催化且高度非对映选择性的直接Michael加成异构序列。观察到在3-酰基香豆素衍生物上意外地将γ-丁内酰胺α-加成，而不是更普遍的γ-加成。加合物可以进一步进行水解/脱羧以产生与通过将γ-丁内酰胺α加成到相应的查耳酮上所获得的产物等同的产物。