7-methoxy-4-(4-methoxyphenyl)coumarin | 23982-32-3

• 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: 7-methoxy-4-(4-methoxyphenyl)coumarin
• 英文别名: 7-methoxy-4-(4-methoxy-phenyl)-coumarin；7-Methoxy-4-(4-methoxy-phenyl)-cumarin；7-Methoxy-4-(4'-methoxyphenyl)-coumarin；7-Methoxy-4-(4-methoxyphenyl)-cumarin；7-methoxy-4-(4-methoxyphenyl)-2H-chromen-2-one；7-methoxy-4-(4-methoxyphenyl)chromen-2-one
• CAS: 23982-32-3
• 化学式: C₁₇H₁₄O₄
• mdl: MFCD03267201
• 分子量: 282.296
• InChiKey: OLCZQQVEYPSHCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-methoxy-4-(4-methoxyphenyl)coumarin 在 吡啶盐酸盐 作用下， 反应 0.4h， 以64%的产率得到7-Hydroxy-4-(4-hydroxy-phenyl)-cumarin
  参考文献：
  名称：

  细胞毒性 4-芳基香豆素的短合成

  摘要：

  摘要描述了在 CF3COOH 存在下，通过酚类与肉桂酸缩合，然后用 DDQ 脱氢，快速合成细胞毒性 4-芳基香豆素。

  DOI：

  10.1080/00397910500501235
• 作为产物：
  描述：

  4-甲氧基肉桂酸 在 氯化亚砜 、 溴 、 三氟乙酸 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 10.33h， 生成 7-methoxy-4-(4-methoxyphenyl)coumarin
  参考文献：
  名称：

  Efficient synthesis and biological evaluation of 4-arylcoumarin derivatives

  摘要：

  Two bioactive natural 4-arylcoumarins, 5,7,4'-trimethoxy-4-phenylcoumarin (1a), 5,7-dimethoxy-4-phenylcoumarin (1b) and five closely related derivatives 1c-g were synthesized. In vitro evaluation with a catechol subunit for antioxidant and antimicrobial activity, these compounds using standard methods showed that compounds id, if displayed promise radical scavenging activity and if was found to be the most active one against Bacillus dysenteriae. (C) 2010 Yong Zou. Published by Elsevier BAT. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2010.12.017

文献信息

• N-Heterocyclic Carbene Derived Nickel-Pincer Complexes: Efficient and Applicable Catalysts for Suzuki-Miyaura Coupling Reactions of Aryl/Alkenyl Tosylates and Mesylates
  作者：Jun-ichi Kuroda、Kiyofumi Inamoto、Kou Hiroya、Takayuki Doi

  DOI：10.1002/ejoc.200900067

  日期：2009.5

  activities of NHC-derived nickel–pincer complexes for the Suzuki–Miyaura coupling reactions of aryl/alkenyl tosylates and mesylates are described. In the presence of a catalytic amount of nickelacycle 1a, a wide array of tosylates and mesylates reacted with several aryl- and alkenylboronic acids to afford the coupling products, generally in high yields. Fine tuning of the reaction conditions for each class

  描述了 NHC 衍生的镍钳配合物对芳基/烯基甲苯磺酸酯和甲磺酸酯的 Suzuki-Miyaura 偶联反应的催化活性。在催化量的镍环 1a 存在下，多种甲苯磺酸盐和甲磺酸盐与几种芳基硼酸和烯基硼酸反应得到偶联产物，通常产率很高。只有通过选择合适的反应介质（甲苯磺酸盐为 DME，甲磺酸盐为二恶烷），才能对每类亲电子​​试剂的反应条件进行微调。（© Wiley-VCH Verlag GmbH & Co. KGaA，69451 Weinheim，德国，2009）
• 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。
• Antioxidant and antitumor activities of 4-arylcoumarins and 4-aryl-3,4-dihydrocoumarins
  作者：Keyun Zhang、Weixian Ding、Jie Sun、Bin Zhang、Fujiao Lu、Ren Lai、Yong Zou、Gabriel Yedid

  DOI：10.1016/j.biochi.2014.03.014

  日期：2014.12

  Five 4-arylcoumarins (1c-g) and twelve 3,4-dihydro-4-arylcoumarins (2a-l) were synthesized and tested for antioxidant activity, antitumor activity, toxicity and structure-activity relationships analysis. 4-Arylcoumarins and 3,4-dihydro-4-arylcoumarins that possess two hydroxyl groups in ortho position, such as 1d, 1f, 2a, 2f, 2g and 2h had stronger radical scavenging properties than that of vitamin C (Vit C) in ABTS(center dot+) assay. Kinetic traces of scavenging ABTS(center dot+) and DPPH radicals showed that all the reaction could reached endpoint in 1 min, which was similar with Vit C. 4-Arylcoumarins with 3'-hydroxyl-4'-methylphenyl structural show more efficient NO center dot radical scavenging activity. Three compounds 2e, 1f and 2a, in particular had superior EC50 for NO center dot scavenging than did Vit C. MTT assay indicated that one compound in particular had a potential antitumor effect, inhibiting proliferation of BGC-823 cells and almost completely killing them at a concentration 62.5 mg/L. With same concentration 100 mu g/mL, hemolytic analysis in rabbit red blood cells showed that only two compounds had hemolytic activity with a little more than 5% hemolysis. Injection and oral toxicity tests on Galleria mellonella larvae showed that none of the tested 4-arylcoumarins significantly affected their appetite, viability and mortality. (C) 2014 Elsevier B.V. and Societe francaise de biochimie et biologie Moleculaire (SFBBM). All rights reserved.
• Bargellini; Leonardi, Gazzetta Chimica Italiana, 1911, vol. 41 I, p. 743
  作者：Bargellini、Leonardi

  DOI：——

  日期：——