(3a,4,9,9a)-4,9-diphenyl-2-(o-tolyl)-3a,4,5,6,9,9a-hexahydro-1H-4,9-epoxybenzo[f]isoindole-1,3(2H)-dione | 1394284-85-5

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基四氢萘木脂素
• 英文名称: (3a,4,9,9a)-4,9-diphenyl-2-(o-tolyl)-3a,4,5,6,9,9a-hexahydro-1H-4,9-epoxybenzo[f]isoindole-1,3(2H)-dione
• 英文别名: (1S,8R,9R,13S)-11-(2-methylphenyl)-1,8-diphenyl-14-oxa-11-azatetracyclo[6.5.1.02,7.09,13]tetradeca-2,4,6-triene-10,12-dione
• CAS: 1394284-85-5
• 化学式: C₃₁H₂₃NO₃
• 分子量: 457.529
• InChiKey: ITLSSJQRPFUSPN-AKAXLSRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  35
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,3-二苯基异苯并呋喃 以 溶剂黄146 、 甲苯 为溶剂， 生成 (3a,4,9,9a)-4,9-diphenyl-2-(o-tolyl)-3a,4,5,6,9,9a-hexahydro-1H-4,9-epoxybenzo[f]isoindole-1,3(2H)-dione
  参考文献：
  名称：

  Do Deuteriums Form Stronger CH−π Interactions?

  摘要：

  The D/H isotope effect for the CH-pi interaction was studied experimentally and computationally. First, a series of molecular balances that are very sensitive to changes in the strength of the CH-pi interactions in solution were designed. Balances with deuterated and non-deuterated alkyl groups were synthesized, and their intramolecular CH-pi interactions were compared. The geometries of their intramolecular CH-pi and CD-pi interactions were characterized in the solid state by X-ray analysis, and the strength of each interaction was characterized in solution by the folded/unfolded ratio as measured by H-1 NMR spectra. Second, the relative strengths of the CH-pi and CD-pi interactions were also assessed computationally using dispersion-corrected DFT (PDE-D2/6-31+G*). No significant differencee was observed in either the experimental or theoretical studies, indicating that the D/H isotope effect for the CH-pi interaction is either very small or nonexistent.

  DOI：

  10.1021/ja305788p

文献信息

• Direct Experimental Evidence for Halogen-Aryl π Interactions in Solution from Molecular Torsion Balances
  作者：Han Sun、André Horatscheck、Vera Martos、Max Bartetzko、Ulrike Uhrig、Dieter Lentz、Peter Schmieder、Marc Nazaré

  DOI：10.1002/anie.201700520

  日期：2017.6.1

  dissected halogen–aryl π interactions experimentally using a bicyclic N-arylimide based molecular torsion balances system, which is based on the influence of the non-bonded interaction on the equilibria between folded and unfolded states. Through comparison of balances modulated by higher halogens with fluorine balances, we determined the magnitude of the halogen–aryl π interactions in our unimolecular

  我们使用基于双环N-芳基酰亚胺的分子扭转平衡系统实验性地分析了卤素-芳基π相互作用，该系统基于非键相互作用对折叠状态和未折叠状态之间的平衡的影响。通过比较高级卤素调节的平衡与氟平衡，我们确定了我们单分子体系中卤素-芳基π相互作用的幅度大于-5.0 kJ mol -1，这与生物分子体系中估计的幅度相当。我们的研究提供了溶液中卤素-芳基π相互作用的直接实验证据，到目前为止，该相互作用仅在固态下才得以揭示，并通过量子力学计算从理论上进行了评估。