9,12-Dimethoxy-3,3,7,7-tetramethyl-3,4,6,7-tetrahydro-2H-dibenzo[b,j][1,7]phenanthrolin-1-one | 146830-32-2

• 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: 9,12-Dimethoxy-3,3,7,7-tetramethyl-3,4,6,7-tetrahydro-2H-dibenzo[b,j][1,7]phenanthrolin-1-one
• 英文别名: 9,12-dimethoxy-3,3,7,7-tetramethyl-4,6-dihydro-2H-quinolino[2,3-c]acridin-1-one
• CAS: 146830-32-2
• 化学式: C₂₆H₂₈N₂O₃
• 分子量: 416.52
• InChiKey: FMABSLKJRMSFSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  31
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  61.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9,12-Dimethoxy-3,3,7,7-tetramethyl-3,4,6,7-tetrahydro-2H-dibenzo[b,j][1,7]phenanthrolin-1-one 在 吡啶-2,6-二羧酸 n-氧化物 、 氢氧化钾 、 ammonium cerium(IV) nitrate 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 25.0h， 生成 15,15,21,21-Tetramethyl-6,18,33,36,38-pentazanonacyclo[20.16.0.02,19.04,17.05,14.07,12.024,37.026,35.029,34]octatriaconta-1(38),2,4(17),5(14),6,9,12,18,22,24,26(35),29(34),30,32,36-pentadecaene-8,11-dione
  参考文献：
  名称：

  Incorporation of the quinoline-5,8-quinone moiety into polyaza cavities

  摘要：

  Silica gel supported nitric acid treatment of 2,5-dimethoxybenzaldehyde followed by reduction with iron powder provides 3,6-dimethoxy-2-aminobenzaldehyde. Friedlander condensation of this species with a variety of ketones and diketones leads to 5,8-dimethoxyquinoline derivatives which may be oxidized by ceric ammonium nitrate (CAN) and pyridine-2,6-dicarboxylic acid N-oxide (PDANO) to the corresponding quinones. The quinone functionality can be incorporated into larger cavities by a selective stepwise Friedlander approach and the CAN/PDANO oxidation appears to work preferentially for 5,8-dimethoxyquinoline.

  DOI：

  10.1021/jo00059a012
• 作为产物：
  描述：

  3,6-二甲氧基-2-硝基苯甲醛 在 盐酸 、 氢氧化钾 、 铁粉 作用下， 以 乙醇 、 水 、 溶剂黄146 为溶剂， 反应 24.25h， 生成 9,12-Dimethoxy-3,3,7,7-tetramethyl-3,4,6,7-tetrahydro-2H-dibenzo[b,j][1,7]phenanthrolin-1-one
  参考文献：
  名称：

  Incorporation of the quinoline-5,8-quinone moiety into polyaza cavities

  摘要：

  Silica gel supported nitric acid treatment of 2,5-dimethoxybenzaldehyde followed by reduction with iron powder provides 3,6-dimethoxy-2-aminobenzaldehyde. Friedlander condensation of this species with a variety of ketones and diketones leads to 5,8-dimethoxyquinoline derivatives which may be oxidized by ceric ammonium nitrate (CAN) and pyridine-2,6-dicarboxylic acid N-oxide (PDANO) to the corresponding quinones. The quinone functionality can be incorporated into larger cavities by a selective stepwise Friedlander approach and the CAN/PDANO oxidation appears to work preferentially for 5,8-dimethoxyquinoline.

  DOI：

  10.1021/jo00059a012