3-(3-(3-hydroxyphenyl)acryloyl)-2H-chromen-2-one | 676618-09-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-(3-(3-hydroxyphenyl)acryloyl)-2H-chromen-2-one
• 英文别名: 3-(3-hydroxycinnamoyl)-coumarin；3-(3-(3-Hydroxyphenyl)acryloyl)-2h-chromen-2-one；3-[3-(3-hydroxyphenyl)prop-2-enoyl]chromen-2-one
• CAS: 676618-09-0
• 化学式: C₁₈H₁₂O₄
• 分子量: 292.291
• InChiKey: VLNRAHCOOOZSCF-UHFFFAOYSA-N

物化性质

• 熔点：
  139-140 °C(Solv: methanol (67-56-1))
• 沸点：
  564.5±50.0 °C(Predicted)
• 密度：
  1.368±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(3-(3-hydroxyphenyl)acryloyl)-2H-chromen-2-one 、 (4-甲基-2-氧代-2H-色烯-7-氧基)-乙酸肼 在 吡啶 作用下， 反应 6.0h， 以85%的产率得到5-(3-hydroxyphenyl)-3-(2-oxo-2H-chromen-3-yl)-1-(4-methyl-2-oxo-2H-chromen-7-yloxyacetyl)-2-pyrazoline
  参考文献：
  名称：

  Synthesis and Biological Evaluation of a Novel Series of 1,3-Dicoumarinyl-5-aryl-2-pyrazolines

  摘要：

  In the present paper novel 1,3,5-trisubstituted 2-pyrazolines (4a-q) were synthesized via condensation of different substituted 3-cinnamoyl-2-oxo-2H-chromenes (2a-q) with 2-(4-methyl-2-oxo-2H-chromen-7-yloxy)acetohydrazide (3). Chalcones were prepared via Claisen-Schmidt condensation by refluxing 3-acetyl-2-oxo-2H-chromen (1) with corresponding aldehydes in ethanol, in the presence of piperidine. All of these compounds were characterized by means of their IR, (1)H NMR and LC/MS/MS spectroscopic data and elemental microanalysis. Chalcones and pyrazolines were screened for their antioxidant and iron chelating activity.

  DOI：

  10.3987/com-11-12196
• 作为产物：
  描述：

  水杨醛 在 哌啶 作用下， 以 氯仿 为溶剂， 反应 1.5h， 生成 3-(3-(3-hydroxyphenyl)acryloyl)-2H-chromen-2-one
  参考文献：
  名称：

  Synthesis and Biological Evaluation of a Novel Series of 1,3-Dicoumarinyl-5-aryl-2-pyrazolines

  摘要：

  In the present paper novel 1,3,5-trisubstituted 2-pyrazolines (4a-q) were synthesized via condensation of different substituted 3-cinnamoyl-2-oxo-2H-chromenes (2a-q) with 2-(4-methyl-2-oxo-2H-chromen-7-yloxy)acetohydrazide (3). Chalcones were prepared via Claisen-Schmidt condensation by refluxing 3-acetyl-2-oxo-2H-chromen (1) with corresponding aldehydes in ethanol, in the presence of piperidine. All of these compounds were characterized by means of their IR, (1)H NMR and LC/MS/MS spectroscopic data and elemental microanalysis. Chalcones and pyrazolines were screened for their antioxidant and iron chelating activity.

  DOI：

  10.3987/com-11-12196

文献信息

• Microwave-assisted synthesis and evaluation of antimicrobial activity of 3-{3-(s-aryl and s-heteroaromatic)acryloyl}-2<i>H</i>-chromen-2-one derivatives
  作者：Olayinka O. Ajani、Obinna C. Nwinyi

  DOI：10.1002/jhet.298

  日期：——

  analytical and spectral data. All the synthesized compounds were screened for their antibacterial activity and 3-3-(4-dimethylaminophenyl)acryloyl}-2H-chromen-2-one () was discovered to be the most active at minimum inhibitory concentration (MIC) value of 7.8 μg/mL. J. Heterocyclic Chem., (2010).

  在本文中，利用缩合反应的方法对微波作为杂环合成能源的潜在利用进行了探索。3-乙酰香豆素（）与芳族和杂芳族醛形成相应的芳族查耳酮（）和杂芳族查耳酮（ 和 ）分别在1-3分钟内达到良好或优异的产量。化学结构通过分析和光谱数据证实。所有合成的化合物筛选它们的抗菌活性和3- 3-（4-二甲基氨基苯基）丙烯酰基} -2- ħ -色烯-2-酮（发现）在7.8μg/ mL的最小抑菌浓度（MIC）值下活性最高。J.杂环化​​学。（2010）。
• Electrochemistry and Reactivity Against Superoxide Anion Radicals of Hydroxycoumarins and Its Derivatives
  作者：C. Barrientos、P. Navarrete-Encina、J. A. Squella

  DOI：10.1149/1945-7111/abcf52

  日期：2020.12.1

  which a radical can act. Electrochemistry is a useful tool for this purpose. In this work, the cyclic voltammetry-based methodology was used to generate superoxide anion radical through oxygen one-electron reduction in a dimethyl sulfoxide solution. Plotting the remaining percentage of initial current against compound concentration we can establish a Reactivity Index (RI50), for comparative purpose

  本研究揭示了对合成香豆素的超氧化物自由基阴离子反应性。自由基在许多疾病中都起着重要作用，并且还具有保护功能。因此，我们必须保持其浓度平衡，这就是香豆素等外源抗氧化剂变得重要的地方。由于自由基可以发挥多种作用机理，因此有多种方法可以量化抗氧化剂的效率。电化学是用于此目的的有用工具。在这项工作中，使用基于循环伏安法的方法通过在二甲亚砜溶液中通过氧单电子还原生成超氧阴离子自由基。将剩余的初始电流百分比与化合物浓度作图，我们可以建立反应活性指数（RI 50），以作比较。该指数是指将初始峰值电流降低50％的浓度值。对电生成的超氧阴离子自由基反应性最高的香豆素是3-乙酰基-7,8-二羟基香豆素（7,8-香豆）。
• Cu(II) and Ni(II) complexes of coumarin derivatives with fourth generation flouroquinolone: synthesis, characterization, microbicidal and antioxidant assay
  作者：Jiten Patel、Hitesh Dholariya、Ketan Patel、Jaimin Bhatt、Kanuprasad Patel

  DOI：10.1007/s00044-014-0943-y

  日期：2014.8
• Synthesis and Biological Evaluation of a Novel Series of 1,3-Dicoumarinyl-5-aryl-2-pyrazolines
  作者：Milan Čačić、Maja Molnar、Ivica Strelec

  DOI：10.3987/com-11-12196

  日期：——

  In the present paper novel 1,3,5-trisubstituted 2-pyrazolines (4a-q) were synthesized via condensation of different substituted 3-cinnamoyl-2-oxo-2H-chromenes (2a-q) with 2-(4-methyl-2-oxo-2H-chromen-7-yloxy)acetohydrazide (3). Chalcones were prepared via Claisen-Schmidt condensation by refluxing 3-acetyl-2-oxo-2H-chromen (1) with corresponding aldehydes in ethanol, in the presence of piperidine. All of these compounds were characterized by means of their IR, (1)H NMR and LC/MS/MS spectroscopic data and elemental microanalysis. Chalcones and pyrazolines were screened for their antioxidant and iron chelating activity.