4-hydroxy-3-(1H-pyrazol-5-yl)chromen-2-one | 1101196-09-1

• 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-(1H-pyrazol-5-yl)chromen-2-one
• CAS: 1101196-09-1
• 化学式: C₁₂H₈N₂O₃
• 分子量: 228.207
• InChiKey: ASPFFMMXJVCLAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-乙酰基-2-羟基苯并吡喃-4-酮 在 一水合肼 作用下， 以 neat (no solvent) 为溶剂， 反应 0.08h， 生成 4-hydroxy-3-(1H-pyrazol-5-yl)chromen-2-one
  参考文献：
  名称：

  Silica supported sodium hydrogen sulfate (NaHSO4–SiO2): A novel, green catalyst for synthesis of pyrazole and pyranyl pyridine derivatives under solvent-free condition via heterocyclic β-enaminones

  摘要：

  NaHSO4-SiO2 is used as an efficient, mild and reusable catalyst for the synthesis of novel heterocyclic pyrazole (5a-h) and pyranyl pyridine (7a-h) derivatives via heterocyclic beta-enaminones (3a-d) under thermal solvent-free conditions. The remarkable features of this green, new methodology are high conversions, cleaner reaction profile, simple experimental and work-up procedures. Structures of the newly synthesized compounds have been elucidated on the basis of elemental analysis and spectral data (IR, H-1 NMR, C-13 NMR and mass spectrometry). The catalyst is characterized for the first time by using scanning electron microscopy-energy dispersive X-ray (SEM-EDX) and powder XRD. The catalyst can be reused several times without significant loss of its catalytic activity. (c) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2012.07.024

文献信息

• Synthesis, spectroscopic and antibacterial investigations of new hydroxy ethers and heterocyclic coumarin derivatives
  作者：Naceur Hamdi、Mustapha Saoud、Antonio Romerosa、Rached Ben Hassen

  DOI：10.1002/jhet.5570450644

  日期：2008.11

  hydroxy ethers 3 and 4 containing coumarin moieties in good yield. The synthesis of 3-(3-(dimethylamino)acryloyl)-4-hydroxy-2H-chromen-2-one 5 and new heterocyclic compounds 4-hydroxy-3-(1H-pyrazol-3-yl)-2H-chromen-2-one 6a, 4-hydroxy-3-(1-phenylpyrazol-3-yl)-2H-chromen-2-one 6b and 4-hydroxy-3-(isoxazol-3-yl)-2H-chromen-2-one 6c is also described. All compounds were characterized by 1H NMR, 13C1H}

  寡乙二醇二缩水甘油醚2a-c与7-羟基-4-甲基-2 H-铬烯-2-酮和4-羟基-2 H-铬烯-2-酮之间的反应导致新的羟基醚3和4含有香豆素部分具有良好的产率。3-（3-（二甲基氨基）丙烯酰基）-4-羟基-2 H-铬烯-2-一5和新的杂环化合物4-羟基-3-（1 H-吡唑-3-基）-2 H的合成-chromen-2-one 6a，4-hydroxy-3-（1-phenylpyrazol-3-yl）-2 H -chromen-2-one 6b和4-hydroxy-3-（isoxazol-3-yl）-2 H -chromen-2-one 6c也进行了描述。所有化合物通过1 H NMR，13 C 1 H} NMR，2D- 1 H- 13 C HMBC，2D- 1 H NOESY NMR，IR和MS光谱进行表征。另外，评估了含有香豆素部分的新产品的抗菌活性。这种活性显然取决于化合物的化学结构。