1-(8-hydroxyquinolin-5-yl)-3-phenylprop-2-en-1-one | 107522-64-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-(8-hydroxyquinolin-5-yl)-3-phenylprop-2-en-1-one
• 英文别名: 1-(8-Hydroxyquinolin-5-yl)-3-phenylprop-2-en-1-one
• CAS: 107522-64-5
• 化学式: C₁₈H₁₃NO₂
• 分子量: 275.307
• InChiKey: JLZNHEYGINZCRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-乙酰基-8-羟基喹啉盐酸盐 在 盐酸 、 sodium acetate 作用下， 以 水 为溶剂， 反应 6.0h， 生成 1-(8-hydroxyquinolin-5-yl)-3-phenylprop-2-en-1-one
  参考文献：
  名称：

  SYNTHESIS OF 8-HYDROXYQUINOLINE CHALCONES: TRANS CONFIGURATION, INTRAMOLECULAR HYDROGEN BONDS, BROMINATION, AND ANTIFUNGAL ACTIVITY

  摘要：

  Nine (8-Hydroxyquinolin-5-yl)-arylpropenones were synthesized and their structures demonstrated by IR and NMR spectroscopy. These molecules showed transconfiguration and strong intramolecular hydrogen bonding; in the IR spectra of 5-formyl-8-hydroxyguinoline, 5-acety1-8-hydroxyquinoline, 1-(8-hydroxyguinolin-5-yl)-3-phenylprop-2-en-1-one and 3-(8-hydroxyquinolin-5-yl)-1-phenylprop-2-en-1-one in CHCl3, besides the known intermolecular hydrogen band (similar to 3180 cm(-1)), we identified the intramolecular hydrogen band OH-N (3460 cm(-1)), the hydrogen bond peaks shifted to low frequency in proton-donor solutions such as phenol and acetic acid (with respect to 8-hydroxyquinoline) and the bonds were broken in trifluoroacetic acid solutions, due to OH protonation; the apolar solvent CCl4 and electrophilic substituents in position 5 in the guillotine ring, limited the formation of the intermolecular hydrogen bonds and, therefore. shifted the similar to 3460 cm(-1) intramolecular hydrogen band to lower frequencies and made it stronger and sharper. The bromination of 3-(8-hydroxyquinolin-5yl)-1-(4-tolyl) prop-2-en-1-one occurred on the activated guillotine fragment, producing monobromo and tetrabromo derivatives, instead of bromination on the aliphatic double bond. Three chalcones tested showed strong antifungal activity in vitro.

  DOI：

  10.4067/s0717-97072012000300019

文献信息

• Synthesis, Characterization, Crystallographic Studies of 5-Acetyl-8-hydroxyquinoline and Their Chalcone Derivatives
  作者：C.B. Vagish、Karthik Kumara、N.K. Lokanath、K. Ajay Kumar、P.G. Chandrasherkar

  DOI：10.14233/ajchem.2020.22628

  日期：——

  and one pot synthesis for the Friedel-Craft acetylation reaction of quinolines was developed. The reaction between 8-hydroxyquinoline and acetyl/benzoyl chloride in nitrobenzene immediately flocculates as yellow precipitate. On further addition of Lewis acid causes the Friedel-Craft acetylation leads to formation of acetylated quionlines in good yields. The structure of compound 5-acetyl-8-hydroxyquinoline

  开发了一种高效、简单的一锅法合成喹啉的弗里德尔-克来福特乙酰化反应。8-羟基喹啉与乙酰基/苯甲酰氯在硝基苯中反应，立即絮凝出黄色沉淀。进一步添加路易斯酸会引起弗里德尔-克来福特乙酰化，从而以良好的产率形成乙酰化喹啉。通过单晶 X 射线衍射研究证实了化合物 5-乙酰基-8-羟基喹啉 (3) 的结构。该化合物结晶为单斜晶系，空间群为P21/c。合成的乙酰化喹啉与芳香醛发生缩合反应，生成 8-羟基喹啉查尔酮衍生物。通过光谱研究、元素分析和单晶 X 射线衍射研究对产品进行了表征。
• SYNTHESIS OF 8-HYDROXYQUINOLINE CHALCONES: TRANS CONFIGURATION, INTRAMOLECULAR HYDROGEN BONDS, BROMINATION, AND ANTIFUNGAL ACTIVITY
  作者：ALONSO J MARRUGO-GONZÁLEZ、VALERIE D ORLOV、ROBERTO FERNANDEZ-MAESTRE

  DOI：10.4067/s0717-97072012000300019

  日期：——

  Nine (8-Hydroxyquinolin-5-yl)-arylpropenones were synthesized and their structures demonstrated by IR and NMR spectroscopy. These molecules showed transconfiguration and strong intramolecular hydrogen bonding; in the IR spectra of 5-formyl-8-hydroxyguinoline, 5-acety1-8-hydroxyquinoline, 1-(8-hydroxyguinolin-5-yl)-3-phenylprop-2-en-1-one and 3-(8-hydroxyquinolin-5-yl)-1-phenylprop-2-en-1-one in CHCl3, besides the known intermolecular hydrogen band (similar to 3180 cm(-1)), we identified the intramolecular hydrogen band OH-N (3460 cm(-1)), the hydrogen bond peaks shifted to low frequency in proton-donor solutions such as phenol and acetic acid (with respect to 8-hydroxyquinoline) and the bonds were broken in trifluoroacetic acid solutions, due to OH protonation; the apolar solvent CCl4 and electrophilic substituents in position 5 in the guillotine ring, limited the formation of the intermolecular hydrogen bonds and, therefore. shifted the similar to 3460 cm(-1) intramolecular hydrogen band to lower frequencies and made it stronger and sharper. The bromination of 3-(8-hydroxyquinolin-5yl)-1-(4-tolyl) prop-2-en-1-one occurred on the activated guillotine fragment, producing monobromo and tetrabromo derivatives, instead of bromination on the aliphatic double bond. Three chalcones tested showed strong antifungal activity in vitro.