(9R,9aS,12aR,13S)-9,13-dimethyl-11-(2-phenoxyphenyl)-12a,13-dihydro-9H-9,13-methanoisoindolo[5,6-f][1,10]-phenthroline-10,12,14(9aH,11H)-trione | 1438243-16-3

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (9R,9aS,12aR,13S)-9,13-dimethyl-11-(2-phenoxyphenyl)-12a,13-dihydro-9H-9,13-methanoisoindolo[5,6-f][1,10]-phenthroline-10,12,14(9aH,11H)-trione
• CAS: 1438243-16-3
• 化学式: C₃₃H₂₃N₃O₄
• 分子量: 525.563
• InChiKey: WVSKUXDFODSCKE-ZAIIWXDFSA-N

物化性质

• 密度：
  1.425±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

反应信息

• 作为反应物：
  描述：

  (9R,9aS,12aR,13S)-9,13-dimethyl-11-(2-phenoxyphenyl)-12a,13-dihydro-9H-9,13-methanoisoindolo[5,6-f][1,10]-phenthroline-10,12,14(9aH,11H)-trione 在 碘甲烷 作用下， 以 丙酮 为溶剂， 反应 12.0h， 以100%的产率得到(9S,9aR,12aS,13R)-4,9,13-trimethyl-10,12,14-trioxo-11-(2-phenoxyphenyl)-9a,10,11,12,12a,13-hexahydro-9H-9,13-methanoisoindolo[5,6-f][1,10]phenanthrolin-4-ium iodide
  参考文献：
  名称：

  Comprehensive Experimental Study of N-Heterocyclic π-Stacking Interactions of Neutral and Cationic Pyridines

  摘要：

  A comprehensive experimental study was carried out by measuring the relative strengths of parallel pi-stacking interactions of N-heterocycles with nonheterocycles. A versatile and rigid model system was developed, which was in equilibrium between a "closed" conformation that forms an intramolecular pi-stacking interaction and an "open" conformation that cannot form the interaction. First, the formation and geometries of the intramolecular N-heterocyclic pi-stacking interactions were verified by X-ray crystallography. Next, the closed/open ratios were measured in solution via integration of the H-1 NMR spectra, providing an accurate comparison of the N-heterocyclic pi-stacking interactions. The synthetic versatility of this model system enabled the systematic and comprehensive comparison of the influences of position, charge, and substituent effects of the nitrogen atom of the N-heterocycles within a single model system. The pi-stacking interactions of the neutral N-heterocyclic rings were slightly stronger than that of nonheterocyclic rings. Cationic N-heterocycles formed significantly stronger pi-stacking interactions than neutral N-heterocycles. The position of the nitrogen atom also had a strong influence on the stability of N-heterocyclic pi-stacking complexes. Interestingly, opposite stability trends were observed for neutral and cationic N-heterocycles. For neural N-heterocycles, geometries with the nitrogen away from the pi-face of the opposing ring were the more stable. For cationic N-heterocycles, geometries with the nitrogen close to the pi-face of the opposing ring were the more stable. Finally, N-methylated heterocycles consistently formed stronger pi-stacking interactions than N-protonated heterocycles.

  DOI：

  10.1021/jo400370e
• 作为产物：
  描述：

  1,10-邻二氮杂菲-5,6-二酮 在 氯化亚砜 、 potassium carbonate 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 (9R,9aS,12aR,13S)-9,13-dimethyl-11-(2-phenoxyphenyl)-12a,13-dihydro-9H-9,13-methanoisoindolo[5,6-f][1,10]-phenthroline-10,12,14(9aH,11H)-trione
  参考文献：
  名称：

  Comprehensive Experimental Study of N-Heterocyclic π-Stacking Interactions of Neutral and Cationic Pyridines

  摘要：

  A comprehensive experimental study was carried out by measuring the relative strengths of parallel pi-stacking interactions of N-heterocycles with nonheterocycles. A versatile and rigid model system was developed, which was in equilibrium between a "closed" conformation that forms an intramolecular pi-stacking interaction and an "open" conformation that cannot form the interaction. First, the formation and geometries of the intramolecular N-heterocyclic pi-stacking interactions were verified by X-ray crystallography. Next, the closed/open ratios were measured in solution via integration of the H-1 NMR spectra, providing an accurate comparison of the N-heterocyclic pi-stacking interactions. The synthetic versatility of this model system enabled the systematic and comprehensive comparison of the influences of position, charge, and substituent effects of the nitrogen atom of the N-heterocycles within a single model system. The pi-stacking interactions of the neutral N-heterocyclic rings were slightly stronger than that of nonheterocyclic rings. Cationic N-heterocycles formed significantly stronger pi-stacking interactions than neutral N-heterocycles. The position of the nitrogen atom also had a strong influence on the stability of N-heterocyclic pi-stacking complexes. Interestingly, opposite stability trends were observed for neutral and cationic N-heterocycles. For neural N-heterocycles, geometries with the nitrogen away from the pi-face of the opposing ring were the more stable. For cationic N-heterocycles, geometries with the nitrogen close to the pi-face of the opposing ring were the more stable. Finally, N-methylated heterocycles consistently formed stronger pi-stacking interactions than N-protonated heterocycles.

  DOI：

  10.1021/jo400370e