3,10-dimethyldibenzo[b,j][1,10]phenanthroline | 195823-25-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: 3,10-dimethyldibenzo[b,j][1,10]phenanthroline
• 英文别名: 3,10-Dimethylquinolino[3,2-c]acridine
• CAS: 195823-25-7
• 化学式: C₂₂H₁₆N₂
• 分子量: 308.382
• InChiKey: SGSZHCNUFSCBJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,10-dimethyldibenzo[b,j][1,10]phenanthroline 在 selenium(IV) oxide 、 萘 作用下， 反应 2.5h， 以56%的产率得到Acridino[5,6-b]quinoline-3,10-dicarbaldehyde
  参考文献：
  名称：

  Cyclobisintercaland Macrocycles:  Synthesis and Physicochemical Properties of Macrocyclic Polyamines Containing Two Crescent-Shaped Dibenzophenanthroline Subunits

  摘要：

  A general access to isomeric dibenzo[bj]phenanthrolinedicarboxaldehydes is described. These pentacyclic planar quinacridine compounds exhibit crescent-shaped forms that fulfill the geometrical requirements of providing broad overlap of nucleobase pairs or triplets. The dialdehyde derivatives have been condensed with various polyamines to give macrocyclic dimeric structures, cyclobisintercalands, of variable size, charge, and shape. The related water-soluble monomeric quinacridines were prepared from the dialdehydes by grafting ammonium groups; The physicochemical properties of the monomeric quinacridines and of the macrocyclic bis-quinacridines have been investigated by spectroscopic methods (UV-vis, fluorescence, NMR). The results show that some of these macrocyclic compounds could exist as semiclosed conformers suitable to accommodate a pair of nucleotides.

  DOI：

  10.1021/jo970496b
• 作为产物：
  描述：

  1,2-二碘苯 在 copper(l) iodide 、 硫酸 、 sodium 、 三氯化铁 、 铜 、 potassium carbonate 作用下， 以 戊醇 为溶剂， 反应 50.0h， 生成 3,10-dimethyldibenzo[b,j][1,10]phenanthroline
  参考文献：
  名称：

  Cyclobisintercaland Macrocycles:  Synthesis and Physicochemical Properties of Macrocyclic Polyamines Containing Two Crescent-Shaped Dibenzophenanthroline Subunits

  摘要：

  A general access to isomeric dibenzo[bj]phenanthrolinedicarboxaldehydes is described. These pentacyclic planar quinacridine compounds exhibit crescent-shaped forms that fulfill the geometrical requirements of providing broad overlap of nucleobase pairs or triplets. The dialdehyde derivatives have been condensed with various polyamines to give macrocyclic dimeric structures, cyclobisintercalands, of variable size, charge, and shape. The related water-soluble monomeric quinacridines were prepared from the dialdehydes by grafting ammonium groups; The physicochemical properties of the monomeric quinacridines and of the macrocyclic bis-quinacridines have been investigated by spectroscopic methods (UV-vis, fluorescence, NMR). The results show that some of these macrocyclic compounds could exist as semiclosed conformers suitable to accommodate a pair of nucleotides.

  DOI：

  10.1021/jo970496b

文献信息

• Improved Synthesis of Quinacridine Derivatives
  作者：Marie-Paule Teulade-Fichou、Rémy Lartia、Hélène Bertrand

  DOI：10.1055/s-2006-932465

  日期：——

  An efficient synthetic pathway toward various substi­tuted quinacridines 1 and 2 has been developed. Compared to the previous method, higher yields and easier workup were obtained.

  已开发出一条合成多种取代喹吖啶1和2的高效合成途径。与之前的方法相比，该方法产量更高，操作更简便。
• Cyclobisintercaland Macrocycles:  Synthesis and Physicochemical Properties of Macrocyclic Polyamines Containing Two Crescent-Shaped Dibenzophenanthroline Subunits
  作者：Olivier Baudoin、Marie-Paule Teulade-Fichou、Jean-Pierre Vigneron、Jean-Marie Lehn

  DOI：10.1021/jo970496b

  日期：1997.8.1

  A general access to isomeric dibenzo[bj]phenanthrolinedicarboxaldehydes is described. These pentacyclic planar quinacridine compounds exhibit crescent-shaped forms that fulfill the geometrical requirements of providing broad overlap of nucleobase pairs or triplets. The dialdehyde derivatives have been condensed with various polyamines to give macrocyclic dimeric structures, cyclobisintercalands, of variable size, charge, and shape. The related water-soluble monomeric quinacridines were prepared from the dialdehydes by grafting ammonium groups; The physicochemical properties of the monomeric quinacridines and of the macrocyclic bis-quinacridines have been investigated by spectroscopic methods (UV-vis, fluorescence, NMR). The results show that some of these macrocyclic compounds could exist as semiclosed conformers suitable to accommodate a pair of nucleotides.