4,7-N,N-Dimethyl-4,7-phenanthroline-3,8-dione | 322400-46-4

• 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: 4,7-N,N-Dimethyl-4,7-phenanthroline-3,8-dione
• 英文别名: 4,7-dimethyl-4,7-phenanthroline-3,8(4H,7H)-dione；4,7-dimethyl-4,7-dihydro-[4,7]phenanthroline-3,8-dione；4,7-Dimethyl-4,7-dihydro-[4,7]phenanthrolin-3,8-dion；4,7-Dimethyl-4,7-phenanthroline-3,8-dione；4,7-dimethyl-4,7-phenanthroline-3,8-dione
• CAS: 322400-46-4
• 化学式: C₁₄H₁₂N₂O₂
• 分子量: 240.261
• InChiKey: OLCPULGFJRJLCQ-UHFFFAOYSA-N

物化性质

• 熔点：
  363-364 °C
• 沸点：
  426.5±45.0 °C(Predicted)
• 密度：
  1.300±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.39
• 重原子数：
  18.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  44.0
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4,7-N,N-Dimethyl-4,7-phenanthroline-3,8-dione 在 三溴化磷 、 三溴氧磷 作用下， 反应 36.0h， 以94%的产率得到3,8-dibromo-4,7-phenanthroline
  参考文献：
  名称：

  Adaptive Self-Assembly: Environment-Induced Formation and Reversible Switching of Polynuclear Metallocyclophanes

  摘要：

  Ligand 3 has been shown to self-assemble under coordination of copper(II) cations in a 1:1 ratio in acetonitrile to give equilibrating mixtures of a [2 x 2] grid-type tetranuclear structure 1 and a hexanuclear achitecture of hexagonal shape 2. The latter was confirmed by determination of the crystal structure which further indicated that 2 contained acetonitrile molecules and hydroxo groups bound to the copper(II) centers, which are therefore five-coordinate. The structures assigned to 1 and 2 were further supported by the spectral (mass, UV/Vis) data. The self-assembly process is strongly dependent on the conditions of the medium. An increase in concentration in acetronitrile increases the relative amount of hexamer 2, which appears to be the favored entity at the highest concentrations that can be reached before precipitation occurs. On the other hand, in nitromethane only the tetranuclear complex 1 was detected by mass spectrometry. Replacement of nitromethane by acetonitrile and vice versa indicated the reversible switching between a solution containing either 1 alone or an equilibrium mixture of 1 and 2, respectively. In conclusion, the system described presents several remarkable features: 1) self-assembly with substrate binding, 2) dynamic combinatorial structure generation, and 3) environment-induced structural switching amounting in effect to a process of adaptive self-assembly.

  DOI：

  10.1002/1521-3765(20001117)6:22<4140::aid-chem4140>3.0.co;2-5
• 作为产物：
  描述：

  4,7-Dimethyl-4,7-phenanthrolinium diiodide 在 Eosin Y 、 caesium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以62%的产率得到4,7-N,N-Dimethyl-4,7-phenanthroline-3,8-dione
  参考文献：
  名称：

  N-烷基吡啶鎓盐在有机光催化下的可见光介导好氧氧化

  摘要：

  喹诺酮类和异喹诺酮类具有多种生物和药物活性，它们的合成在温和条件下非常理想。在这里，以曙红Y为有机光催化剂，空气为末端氧化剂，开发了一种高效且环保的可见光介导的易获得的N-烷基吡啶盐的有氧氧化，该反应以良好的收率提供了喹诺酮类和异喹诺酮类。该方法显示出许多优点，包括条件温和、环境友好、效率高、对宽官能团的耐受性和成本低。此外，使用我们的方法有效地制备了具有重要药物活性的4-脱氧亚胺。因此，本方法应为合成和修饰 N-杂环提供一种新颖且有用的策略。

  DOI：

  10.1021/jacs.7b07883

文献信息

• DOUGLAS; JACOMB; KERMACK, Journal of the Chemical Society, 1947, vol. 1, p. 1659 - 1661
  作者：DOUGLAS、JACOMB、KERMACK

  DOI：——

  日期：——
• Kaufmann; Radosevic, Chemische Berichte, 1909, vol. 42, p. 2613 Anm. 1
  作者：Kaufmann、Radosevic

  DOI：——

  日期：——
• DE654444
  申请人：——

  公开号：——

  公开（公告）日：——