3-(8-羟基喹啉-5-基)-1-(4-甲基苯基)丙-2-烯-1-酮 | 833488-10-1

• 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
• 中文名称: 3-(8-羟基喹啉-5-基)-1-(4-甲基苯基)丙-2-烯-1-酮
• 英文名称: 3-(8-hydroxyquinolin-5-yl)-1-(4-tolyl)prop-2-en-1-one
• 英文别名: 3-(8-Hydroxyquinolin-5-yl)-1-(4-methylphenyl)prop-2-en-1-one；3-(8-hydroxyquinolin-5-yl)-1-(4-methylphenyl)prop-2-en-1-one
• CAS: 833488-10-1
• 化学式: C₁₉H₁₅NO₂
• 分子量: 289.334
• InChiKey: UZSKNOLLNHKJTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(8-羟基喹啉-5-基)-1-(4-甲基苯基)丙-2-烯-1-酮 在 溴 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以70%的产率得到3-(7-bromo-8-hydroxyquinolin-5-yl)-1-(4-tolyl)prop-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
• 作为产物：
  描述：

  8-羟基喹啉 在 盐酸 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 20.0h， 生成 3-(8-羟基喹啉-5-基)-1-(4-甲基苯基)丙-2-烯-1-酮
  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 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.