4-hydroxy-3-[3-(4-methylphenyl)prop-2-enoyl]chromen-2-one | 61444-72-2

• 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: 4-hydroxy-3-[3-(4-methylphenyl)prop-2-enoyl]chromen-2-one
• CAS: 61444-72-2
• 化学式: C₁₉H₁₄O₄
• 分子量: 306.318
• InChiKey: JINVYSWGVHELTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  67.51
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-hydroxy-3-[3-(4-methylphenyl)prop-2-enoyl]chromen-2-one 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以49%的产率得到4-hydroxy-3-[5-(4-methylphenyl)-4,5-dihydro-1H-pyrazol-3-yl]coumarin
  参考文献：
  名称：

  分子间π···π相互作用在新型香豆素基吡唑啉材料的发光行为中的作用

  摘要：

  合成了九种基于香豆素的吡唑啉并对其进行了全面表征，以寻找用于设计刺激响应性铬材料的新型荧光化合物。所有报告的化合物在溶液和固态下均表现为高荧光物质，分子间相互作用在其光物理性质中起关键作用。特别是化合物1a由于分子间π··π过渡的建立和/或破裂而表现出不可逆的热，机械，溶剂化和气相致变色行为，此外，由于添加了几种金属而形成的络合，其离子致变色性质盐。粉末XRD研究已经进行，以解释所述的刺激反应效应。化合物1a分子具有π··π相互作用，这是通过六元环的质心之间的短距离3.61（2）Å和弱的分子间C–H…O氢键来证明的，这些分子将π···π二聚体连接到列。根据具有B3LYP功能的TD DFT方法的量子化学计算，以def2-TZVP为基础，分子间π···π相互作用导致1a的电子吸收（EA）发生强烈的红移（约63 nm）。固态。相反，在2a结构中，没有任何有关π···π堆积的提示，并且从溶液到固态

  DOI：

  10.1016/j.dyepig.2020.108942
• 作为产物：
  描述：

  4-羟基香豆素 在 哌啶 、 三氯氧磷 作用下， 以 氯仿 为溶剂， 生成 4-hydroxy-3-[3-(4-methylphenyl)prop-2-enoyl]chromen-2-one
  参考文献：
  名称：

  Design, synthesis and biological evaluation of some novel 3-cinnamoyl-4-hydroxy-2H-chromen-2-ones as antimalarial agents

  摘要：

  A novel series of 3-cinnamoyl-4-hydroxy-2H-chromen-2-ones were designed, synthesized and screened for antiplasmodial activity. Eleven compounds of the series exhibited micromolar potency against chloroquine sensitive and chloroquine resistant strains. The most potent compound 4-hydroxy-3-(3-(4-nitrophenyl)acryloyl)-2H-chromen-2-one showed inhibitory potency (IC50) of 3.1 and 4 mu g/ml against chloroquine sensitive and chloroquine resistant strains, respectively. A structure activity relationship study was performed by correlating the effect of substituents with the antimalarial activity of the title compounds. The novel 3-cinnamoyl-4-hydroxy-2H-chromen-2-ones reported here should be good lead for further development of antimalarial agents that can overcome resistance.

  DOI：

  10.1007/s00044-011-9694-1

文献信息

• The role of the intermolecular π···π interactions in the luminescence behavior of novel coumarin-based pyrazoline materials
  作者：V.F. Traven、D.A. Cheptsov、J.I. Svetlova、I.V. Ivanov、Cristián Cuerva、Carlos Lodeiro、Frederico Duarte、S.F. Dunaev、V.V. Chernyshev

  DOI：10.1016/j.dyepig.2020.108942

  日期：2021.2

  effects. The compound 1a molecules have π···π interactions proved by short distance of 3.61(2) Å between the centroids of six-membered cycles and weak intermolecular C–H…O hydrogen bonds, which link the π···π dimers into columns. According to quantum chemical calculations by TD DFT method with the B3LYP functional, in the def2-TZVP basis, intermolecular π···π interactions lead to strong red-shift (around

  合成了九种基于香豆素的吡唑啉并对其进行了全面表征，以寻找用于设计刺激响应性铬材料的新型荧光化合物。所有报告的化合物在溶液和固态下均表现为高荧光物质，分子间相互作用在其光物理性质中起关键作用。特别是化合物1a由于分子间π··π过渡的建立和/或破裂而表现出不可逆的热，机械，溶剂化和气相致变色行为，此外，由于添加了几种金属而形成的络合，其离子致变色性质盐。粉末XRD研究已经进行，以解释所述的刺激反应效应。化合物1a分子具有π··π相互作用，这是通过六元环的质心之间的短距离3.61（2）Å和弱的分子间C–H…O氢键来证明的，这些分子将π···π二聚体连接到列。根据具有B3LYP功能的TD DFT方法的量子化学计算，以def2-TZVP为基础，分子间π···π相互作用导致1a的电子吸收（EA）发生强烈的红移（约63 nm）。固态。相反，在2a结构中，没有任何有关π···π堆积的提示，并且从溶液到固态
• Design, synthesis and biological evaluation of some novel 3-cinnamoyl-4-hydroxy-2H-chromen-2-ones as antimalarial agents
  作者：Kuldeep Patel、Chandrabose Karthikeyan、N. S. Hari Narayana Moorthy、Girdhar Singh Deora、Viswas Raja Solomon、Hoyun Lee、Piyush Trivedi

  DOI：10.1007/s00044-011-9694-1

  日期：2012.8

  A novel series of 3-cinnamoyl-4-hydroxy-2H-chromen-2-ones were designed, synthesized and screened for antiplasmodial activity. Eleven compounds of the series exhibited micromolar potency against chloroquine sensitive and chloroquine resistant strains. The most potent compound 4-hydroxy-3-(3-(4-nitrophenyl)acryloyl)-2H-chromen-2-one showed inhibitory potency (IC50) of 3.1 and 4 mu g/ml against chloroquine sensitive and chloroquine resistant strains, respectively. A structure activity relationship study was performed by correlating the effect of substituents with the antimalarial activity of the title compounds. The novel 3-cinnamoyl-4-hydroxy-2H-chromen-2-ones reported here should be good lead for further development of antimalarial agents that can overcome resistance.