2,6,8-triphenyl-2,3-dihydroquinolin-4(1H)-one | 1332337-51-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,6,8-triphenyl-2,3-dihydroquinolin-4(1H)-one
• 英文别名: 2,6,8-triphenyl-2,3-dihydro-1H-quinolin-4-one
• CAS: 1332337-51-5
• 化学式: C₂₇H₂₁NO
• 分子量: 375.47
• InChiKey: GZSLCIRQOCOKGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,6,8-triphenyl-2,3-dihydroquinolin-4(1H)-one 在 thallium(III) p-tosylate 作用下， 以 乙二醇二甲醚 为溶剂， 反应 0.5h， 以66%的产率得到2,6,8-triphenylquinolin-4(1H)-one
  参考文献：
  名称：

  Suzuki–Miyaura cross-coupling of 2-aryl-6,8-dibromo-1,2,3,4-tetrahydroquinolin-4-ones and subsequent dehydrogenation and oxidative aromatization of the resulting 2,6,8-triaryl-1,2,3,4-tetrahydroquinolin-4-ones

  摘要：

  Dichlorobis(triphenylphosphine)palladium(II)/tricyclohexylphosphine-catalyzed Suzuki-Miyaura cross-coupling of the 2-aryl-6,8-dibromo-1,2,3,4-tetrahydroquinolin-4-ones with arylboronic acids afforded the corresponding 2,6,8-triaryl-1,2,3,4-tetrahydroquinolin-4-ones, exclusively. The latter was subjected to thallium(III) p-tolylsulfonate (TTS) in dimethoxyethane under reflux or to molecular iodine in methanol at reflux to afford the 2,6,8-triarylquinolin-4-(1H)-ones and 2,6,8-triaryl-4-methoxyquinoline derivatives, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.085
• 作为产物：
  描述：

  2,3-二氢-2-苯基-4(1H)-喹啉 在 bis-triphenylphosphine-palladium(II) chloride 、 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 、 三环己基膦 作用下， 以 1,4-二氧六环 、 四氯化碳 、 氯仿 、 水 为溶剂， 反应 21.0h， 生成 2,6,8-triphenyl-2,3-dihydroquinolin-4(1H)-one
  参考文献：
  名称：

  Suzuki–Miyaura cross-coupling of 2-aryl-6,8-dibromo-1,2,3,4-tetrahydroquinolin-4-ones and subsequent dehydrogenation and oxidative aromatization of the resulting 2,6,8-triaryl-1,2,3,4-tetrahydroquinolin-4-ones

  摘要：

  Dichlorobis(triphenylphosphine)palladium(II)/tricyclohexylphosphine-catalyzed Suzuki-Miyaura cross-coupling of the 2-aryl-6,8-dibromo-1,2,3,4-tetrahydroquinolin-4-ones with arylboronic acids afforded the corresponding 2,6,8-triaryl-1,2,3,4-tetrahydroquinolin-4-ones, exclusively. The latter was subjected to thallium(III) p-tolylsulfonate (TTS) in dimethoxyethane under reflux or to molecular iodine in methanol at reflux to afford the 2,6,8-triarylquinolin-4-(1H)-ones and 2,6,8-triaryl-4-methoxyquinoline derivatives, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.085

文献信息

• Suzuki–Miyaura cross-coupling of 2-aryl-6,8-dibromo-1,2,3,4-tetrahydroquinolin-4-ones and subsequent dehydrogenation and oxidative aromatization of the resulting 2,6,8-triaryl-1,2,3,4-tetrahydroquinolin-4-ones
  作者：Malose J. Mphahlele、Felix A. Oyeyiola

  DOI：10.1016/j.tet.2011.06.085

  日期：2011.9

  Dichlorobis(triphenylphosphine)palladium(II)/tricyclohexylphosphine-catalyzed Suzuki-Miyaura cross-coupling of the 2-aryl-6,8-dibromo-1,2,3,4-tetrahydroquinolin-4-ones with arylboronic acids afforded the corresponding 2,6,8-triaryl-1,2,3,4-tetrahydroquinolin-4-ones, exclusively. The latter was subjected to thallium(III) p-tolylsulfonate (TTS) in dimethoxyethane under reflux or to molecular iodine in methanol at reflux to afford the 2,6,8-triarylquinolin-4-(1H)-ones and 2,6,8-triaryl-4-methoxyquinoline derivatives, respectively. (C) 2011 Elsevier Ltd. All rights reserved.