(9R,9aS,12aR,13S)9,13-diphenyl-11-(2-(pyridin-3-yloxy)phenyl)-12a,13-dihydro-9H-9,13-methanophenanthro[9,10-f]isoindole-10,12,14(9aH,11H)-trione | 1438384-23-6

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: (9R,9aS,12aR,13S)9,13-diphenyl-11-(2-(pyridin-3-yloxy)phenyl)-12a,13-dihydro-9H-9,13-methanophenanthro[9,10-f]isoindole-10,12,14(9aH,11H)-trione
• 英文别名: (1S,16R,17R,21S)-1,16-diphenyl-19-(2-pyridin-3-yloxyphenyl)-19-azahexacyclo[14.5.1.02,15.03,8.09,14.017,21]docosa-2(15),3,5,7,9,11,13-heptaene-18,20,22-trione
• CAS: 1438384-23-6
• 化学式: C₄₄H₂₈N₂O₄
• 分子量: 648.717
• InChiKey: WVZKDXVITGBGGS-PMWRMWSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  50
• 可旋转键数：
  5
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  76.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (9R,9aS,12aR,13S)9,13-diphenyl-11-(2-(pyridin-3-yloxy)phenyl)-12a,13-dihydro-9H-9,13-methanophenanthro[9,10-f]isoindole-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1-methyl-3-(2-((9R,9aR,12aS,13S)-10,12,14-trioxo-9,13-diphenyl-9a,10,12a,13-tetrahydro-9H-9,13-methanophenanthro[9,10-f]isoindolo-11(12H)-yl)phenoxy)-pyridin-1-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：

  3-(2-nitrophenoxy)pyridine 在 palladium on activated charcoal 、 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 (9R,9aS,12aR,13S)9,13-diphenyl-11-(2-(pyridin-3-yloxy)phenyl)-12a,13-dihydro-9H-9,13-methanophenanthro[9,10-f]isoindole-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