3,3-dibenzyl-1H-quinoline-2,4-dione | 20886-12-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3,3-dibenzyl-1H-quinoline-2,4-dione
• 英文别名: 3,3-Dibenzyl-2,4-dioxo-1,2,3,4-tetrahydrochinolin
• CAS: 20886-12-8
• 化学式: C₂₃H₁₉NO₂
• 分子量: 341.409
• InChiKey: VLPXLRKHFGGMSG-UHFFFAOYSA-N

物化性质

• 沸点：
  555.5±39.0 °C(Predicted)
• 密度：
  1.217±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,3-dibenzyl-1H-quinoline-2,4-dione 在 sodium tetrahydroborate 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 以99%的产率得到3,3-dibenzyl-4-hydroxy-3,4-dihydro-1H-quinolin-2-one
  参考文献：
  名称：

  Synthesis of symmetrically substituted 3,3-dibenzyl-4-hydroxy-3,4-dihydro-1H-quinolin-2-ones, as novel quinoline derivatives with antibacterial activity

  摘要：

  A novel series of symmetrically substituted 3,3-dibenzy1-4-hydroxy-3,4-dihydro-1H-quinolin-2-ones was synthesized and tested as antimicrobials. The minimum inhibitory concentration (MIC) values of the most active heterocycles were slightly higher than those exhibited by levofloxacin, employed as comparator. Structural factors affecting the activity were explored along three diversification points, including the substituents of the aromatic rings of the 3-benzyl moieties, as well as the functionalization of both, the homocyclic ring of the heterocycle and the quinolonic nitrogen atom. 6-Chloro and 3,3-bis(4'-chlorobenzyl) derivatives showed the lower MIC values. Optimally substituted heterocycles were synthesized, which exhibited enhanced activity. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.024
• 作为产物：
  描述：

  N,N'-二(苯基)丙二酰胺 在 potassium carbonate 作用下， 以 水 、 甲苯 为溶剂， 反应 54.0h， 生成 3,3-dibenzyl-1H-quinoline-2,4-dione
  参考文献：
  名称：

  Synthesis of symmetrically substituted 3,3-dibenzyl-4-hydroxy-3,4-dihydro-1H-quinolin-2-ones, as novel quinoline derivatives with antibacterial activity

  摘要：

  A novel series of symmetrically substituted 3,3-dibenzy1-4-hydroxy-3,4-dihydro-1H-quinolin-2-ones was synthesized and tested as antimicrobials. The minimum inhibitory concentration (MIC) values of the most active heterocycles were slightly higher than those exhibited by levofloxacin, employed as comparator. Structural factors affecting the activity were explored along three diversification points, including the substituents of the aromatic rings of the 3-benzyl moieties, as well as the functionalization of both, the homocyclic ring of the heterocycle and the quinolonic nitrogen atom. 6-Chloro and 3,3-bis(4'-chlorobenzyl) derivatives showed the lower MIC values. Optimally substituted heterocycles were synthesized, which exhibited enhanced activity. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.024

文献信息

• 2,2,2-trifluoroethanol-promoted access to symmetrically 3,3-disubstituted quinoline-2,4-diones
  作者：Marcel Manke Selvero、Gabriela N. Ledesma、Ulrich Abram、Ernesto Schulz-Lang、Ademir Farias Morel、Enrique L. Larghi

  DOI：10.1016/j.jfluchem.2020.109520

  日期：2020.6

  unprecedented use of 2,2,2-trifluoroethanol as reaction solvent provided a facile and convenient access to symmetrically 3,3-disubstitued quinoline-2,4-diones in moderate to excellent yields and high regioselectivity, by reaction of 4-hydroxy-2-quinolones with electrophiles like methyl iodide, as well as benzyl and allyl bromides in the presence of K2CO3. Silver (I) oxide is required to increase the yield of

  通过2,2,2-三氟乙醇作为反应溶剂的空前使用，通过4-羟基-苯酚的反应，以中等至极好的收率和高区域选择性提供了一种方便且便捷的途径，可对称地获得3,3-二取代的喹啉-2,4-二酮。在K 2 CO 3存在下，具有亲电试剂的2-喹诺酮类化合物，如甲基碘，以及苄基和烯丙基溴。需要氧化银（I）以增加甲基化的产率。
• Synthesis of symmetrically substituted 3,3-dibenzyl-4-hydroxy-3,4-dihydro-1H-quinolin-2-ones, as novel quinoline derivatives with antibacterial activity
  作者：Matías D. Ferretti、Alexandre T. Neto、Ademir F. Morel、Teodoro S. Kaufman、Enrique L. Larghi

  DOI：10.1016/j.ejmech.2014.05.024

  日期：2014.6

  A novel series of symmetrically substituted 3,3-dibenzy1-4-hydroxy-3,4-dihydro-1H-quinolin-2-ones was synthesized and tested as antimicrobials. The minimum inhibitory concentration (MIC) values of the most active heterocycles were slightly higher than those exhibited by levofloxacin, employed as comparator. Structural factors affecting the activity were explored along three diversification points, including the substituents of the aromatic rings of the 3-benzyl moieties, as well as the functionalization of both, the homocyclic ring of the heterocycle and the quinolonic nitrogen atom. 6-Chloro and 3,3-bis(4'-chlorobenzyl) derivatives showed the lower MIC values. Optimally substituted heterocycles were synthesized, which exhibited enhanced activity. (C) 2014 Elsevier Masson SAS. All rights reserved.