7-hydroxy-3,4,5-trimethylcoumarin | 109497-58-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 7-hydroxy-3,4,5-trimethylcoumarin
• 英文别名: 7-hydroxy-3,4,5-trimethyl-2H-1-benzopyran-2-one；7-Hydroxy-3,4,5-trimethyl-cumarin；7-hydroxy-3,4,5-trimethylchromen-2-one
• CAS: 109497-58-7
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: VFNRQAVUWZVXPF-UHFFFAOYSA-N

物化性质

• 熔点：
  195-197 °C(Solv: ethanol (64-17-5); acetic acid, 50% (64-19-7))
• 沸点：
  393.7±42.0 °C(Predicted)
• 密度：
  1.217±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  7-hydroxy-3,4,5-trimethylcoumarin 、 碘甲烷 在 potassium carbonate 、 丙酮 作用下， 生成 7-methoxy-3,4,5-trimethyl-coumarin
  参考文献：
  名称：

  Sethna; Shah, Journal of the Indian Chemical Society, 1940, vol. 17, p. 487,490

  摘要：

  DOI：
• 作为产物：
  描述：

  7-hydroxy-3,5-dimethyl-4-(2-oxo-butyl)-chromen-2-one 在 sodium hydroxide 作用下， 生成 7-hydroxy-3,4,5-trimethylcoumarin
  参考文献：
  名称：

  Sethna; Shah, Journal of the Indian Chemical Society, 1940, vol. 17, p. 487,490

  摘要：

  DOI：

文献信息

• 7-(2-Oxoalkoxy)coumarins: Synthesis and Anti-Inflammatory Activity of a Series of Substituted Coumarins
  作者：Juri Timonen、Katriina Vuolteenaho、Tiina Leppänen、Riina Nieminen、Eeva Moilanen、Paula Aulaskari、Janne Jänis

  DOI：10.1002/jhet.2173

  日期：2015.9

  A series of 7‐(2‐oxoalkoxy)coumarins have been synthesized by conjugating substituted 7‐hydroxycoumarins with different chloroketones. The anti‐inflammatory properties of 7‐(2‐oxoalkoxy)coumarins were studied in LPS‐induced inflammatory response in J774 macrophages. Western blot was used to determine the expression of iNOS and COX‐2, NO was determined by measuring its metabolite nitrite by Griess reaction

  通过将取代的7-羟基香豆素与不同的氯酮缀合，可以合成一系列7-（2-氧代烷氧基）香豆素。在L774诱导的J774巨噬细胞的炎症反应中研究了7-（2-氧代烷氧基）香豆素的抗炎特性。用Western印迹法测定iNOS和COX-2的表达，通过Griess反应测定其代谢产物亚硝酸盐测定NO，通过ELISA测定IL-6。在100μM的浓度下，有17种被研究的化合物抑制NO和IL-6的产生超过50％。最佳抑制剂的IC 50值对于化合物12为21μM/ 24μM（NO / IL-6），对于化合物20为30μM/ 10μM（NO / IL-6）。主要结果是，被7-（2-氧代烷氧基）取代可改善大多数研究的7-羟基香豆素的抗炎特性。
• Synthesis and anti-inflammatory effects of a series of novel 7-hydroxycoumarin derivatives
  作者：Juri M. Timonen、Riina M. Nieminen、Outi Sareila、Antonis Goulas、Lauri J. Moilanen、Matti Haukka、Pirjo Vainiotalo、Eeva Moilanen、Paula H. Aulaskari

  DOI：10.1016/j.ejmech.2011.05.052

  日期：2011.9

  A number of 7-hydroxycoumarins have been synthesised by Pechmann cyclisation using differently substituted resorcinols employing perchloric acid as the condensing agent. All the compounds have been characterised by analytical and spectroscopic methods. The anti-inflammatory properties were tested with LPS-induced inflammation in J774 macrophages. Expression of iNOS and COX-2 was determined by Western

  使用高氯酸作为缩合剂，使用不同取代的间苯二酚，通过Pechmann环化合成了许多7-羟基香豆素。所有化合物均已通过分析和光谱方法表征。用LPS诱导的J774巨噬细胞中的炎症测试了抗炎特性。通过蛋白质印迹法测定iNOS和COX-2的表达，通过亚硝酸盐测定法测定NO，通过ELISA分析测定IL-6。被测试的7-羟基香豆素中有15种也抑制IL-6的产生，但是它们都没有对COX-2的表达产生任何重要的抑制作用。
• Introduction of poly(4-vinylpyridinium) perchlorate as a new, efficient, and versatile solid acid catalyst for one-pot synthesis of substituted coumarins under ultrasonic irradiation
  作者：Nader Ghaffari Khaligh、Farhad Shirini

  DOI：10.1016/j.ultsonch.2012.07.013

  日期：2013.1

  Poly(4-vinylpyridinium) perchlorate, is a supported, recyclable, eco-benign catalyst for synthesis of substituted coumarins via Pechmann reaction using ultrasound irradiation at room temperature and neat condition in high yields with short reaction times. The catalyst was studied by FT-IR, X-ray diffraction, scanning electron microscope, thermo-gravimetric and energy dispersion X-ray analyses. All the products were extensively characterized by H-1 NMR, FT-IR, MS and melting point analyses. This methodology offers momentous improvements over various options for the synthesis of coumarins with regard to yield of products, simplicity in operation and green aspects by avoiding toxic catalysts and solvents. Further, the catalyst can be reused and recovered for several times without loss of activity. (C) 2012 Elsevier B.V. All rights reserved.
• SYNTHESIS OF COUMARINS CATALYZED BY ECO-FRIENDLY W/ZrO₂SOLID ACID CATALYST
  作者：Benjaram M. Reddy、Vangala R. Reddy、D. Giridhar

  DOI：10.1081/scc-100107007

  日期：2001.1

  Synthesis of substituted coumarins via reactions of resorcinol and substituted resorcinol with ethyl acetoacetate and ethyl alpha -methylacetoacetate (Pechmann reaction) are reported, in which the production of environmentally harmful waste streams is minimized by the use of a novel solid acid catalyst.
• Synthesis, anti-browning effect and mechanism research of kojic acid-coumarin derivatives as anti-tyrosinase inhibitors
  作者：Min He、Jinfeng Zhang、Na Li、Lu Chen、Yan He、Zhiyun Peng、Guangcheng Wang

  DOI：10.1016/j.fochx.2024.101128

  日期：2024.3