3,3-bis[2-hydroperoxy-2,2-bis(4-methylphenyl)ethyl]-1-methylquinoline-2,4(1H,3H)-dione

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3,3-bis[2-hydroperoxy-2,2-bis(4-methylphenyl)ethyl]-1-methylquinoline-2,4(1H,3H)-dione
• 英文别名: 3,3-Bis[2-hydroperoxy-2,2-bis(4-methylphenyl)ethyl]-1-methylquinoline-2,4-dione；3,3-bis[2-hydroperoxy-2,2-bis(4-methylphenyl)ethyl]-1-methylquinoline-2,4-dione
• 化学式: C₄₂H₄₁NO₆
• 分子量: 655.791
• InChiKey: GYMWDXJTZNWBJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  49
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  96.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-羟基-N-甲基-2-喹啉 、 1,1-二(对甲苯)乙烯 在 air 、 manganese triacetate 作用下， 以 溶剂黄146 为溶剂， 反应 4.0h， 以59%的产率得到3,3-bis[2-hydroperoxy-2,2-bis(4-methylphenyl)ethyl]-1-methylquinoline-2,4(1H,3H)-dione
  参考文献：
  名称：

  基于Mn（III）催化的好氧氧化的独特过氧化物形成

  摘要：

  在催化量的乙酸锰（III）二水合物存在下，在空气中将1,1-二芳基取代的烯烃4和4-羟基-1 H-喹啉-2-酮5的混合物进行自氧化，得到3,3-bis（ 2-氢过氧乙基）-1 H-喹啉-2,4-二酮6的产率为31-91％，与[4.4.3]丙炔型环状过氧化物7（10-34％）一起产生。3-取代的喹啉酮8的类似的需氧氧化产生环过氧化物衍生物9和/或3-氢过氧乙基化的喹啉二酮10，这取决于取代基。双（氢过氧化物）6（R 1 = Me，Ar = 4-ClC通过X射线晶体学证实了6 H 4）和[4.4.3]丙炔7（R 1 = Me，Ar = Ph）。

  DOI：

  10.1016/j.tetlet.2003.11.054

文献信息

• A unique peroxide formation based on the Mn(III)-catalyzed aerobic oxidation
  作者：Ryoukou Kumabe、Hiroshi Nishino

  DOI：10.1016/j.tetlet.2003.11.054

  日期：2004.1

  1-diarylsubstituted alkenes 4 and 4-hydroxy-1H-quinolin-2-ones 5 in the presence of a catalytic amount of manganese(III) acetate dihydrate in air gave 3,3-bis(2-hydroperoxyethyl)-1H-quinoline-2,4-diones 6 in 31–91% yields together with [4.4.3]propellane-type cyclic peroxides 7 (10–34%). A similar aerobic oxidation of 3-substituted quinolinones 8 yielded cyclic peroxide derivatives 9 and/or 3-hydroperoxyethylated

  在催化量的乙酸锰（III）二水合物存在下，在空气中将1,1-二芳基取代的烯烃4和4-羟基-1 H-喹啉-2-酮5的混合物进行自氧化，得到3,3-bis（ 2-氢过氧乙基）-1 H-喹啉-2,4-二酮6的产率为31-91％，与[4.4.3]丙炔型环状过氧化物7（10-34％）一起产生。3-取代的喹啉酮8的类似的需氧氧化产生环过氧化物衍生物9和/或3-氢过氧乙基化的喹啉二酮10，这取决于取代基。双（氢过氧化物）6（R 1 = Me，Ar = 4-ClC通过X射线晶体学证实了6 H 4）和[4.4.3]丙炔7（R 1 = Me，Ar = Ph）。
• Mn(III)-based reaction of alkenes with quinolinones. Formation of peroxyquinolinones and quinoline-related derivatives
  作者：Hiroshi Nishino、Ryoukou Kumabe、Ryoichi Hamada、Mehtap Yakut

  DOI：10.1016/j.tet.2014.01.013

  日期：2014.2

  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.