3,5-dihydro-5-methyl-2-(2,2-diphenylethenyl)furo[3,2-c]quinolin-4(2H)-one | 1556997-69-3

• 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: 3,5-dihydro-5-methyl-2-(2,2-diphenylethenyl)furo[3,2-c]quinolin-4(2H)-one
• 英文别名: 2-(2,2-Diphenylethenyl)-5-methyl-2,3-dihydrofuro[3,2-c]quinolin-4-one
• CAS: 1556997-69-3
• 化学式: C₂₆H₂₁NO₂
• 分子量: 379.458
• InChiKey: NOBLFDGYQJPNON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-羟基-N-甲基-2-喹啉 、 1,1-二苯基-1,3-丁二烯 在 manganese(III) triacetate dihydrate 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以71%的产率得到3,5-dihydro-5-methyl-2-(2,2-diphenylethenyl)furo[3,2-c]quinolin-4(2H)-one
  参考文献：
  名称：

  Mn(III)-based reaction of alkenes with quinolinones. Formation of peroxyquinolinones and quinoline-related derivatives

  摘要：

  The reactions of 1,1-disubstituted alkenes with 4-hydroxyquinolin-2(1H)-ones under both Mn(III)-catalyzed aerobic oxidation conditions at room temperature and Mn(III)-mediated oxidation conditions at reflux temperature are described. The Mn(III)-catalyzed aerobic oxidation afforded bis(hydroperoxyethyl)quinolinones and azatrioxa[4.431propellanes, while the oxidation with Mn(OAc)(3)center dot 2H(2)O produced furo[3,2-c]quinolin-4-one analogues. The existence of a substituent at the 3-position of the 4-hydroxyquinolin-2(1H)-ones prevented a double reaction with the alkenes, and (endoperoxy)quinolinones and/or (hydroperoxyethyl)quinolinones were obtained under the Mn(III)-catalyzed aerobic conditions, while furo[3,2-c]quinolinone hemiacetals and vinylquinolinones were selectively produced under the Mn(III)-mediated oxidation conditions depending on the reaction temperature and times. Cyclic assembly of quinolinone-related 1,3-dicarbonyl compounds such as dihydropyridinones, pyranones, and dimedone derivatives was also examined under elevated temperature conditions. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.01.013