9-(4-trifluoromethylbenzyl)-1,4-dihydroxytriptycene | 852123-48-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9-(4-trifluoromethylbenzyl)-1,4-dihydroxytriptycene
• 英文别名: 1-[[4-(Trifluoromethyl)phenyl]methyl]pentacyclo[6.6.6.02,7.09,14.015,20]icosa-2,4,6,9,11,13,15,17,19-nonaene-3,6-diol
• CAS: 852123-48-9
• 化学式: C₂₈H₁₉F₃O₂
• 分子量: 444.453
• InChiKey: IGLDRPDKUNLCFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  33
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9-(4-trifluoromethylbenzyl)-1,4-dihydroxytriptycene 、 五氟苯甲酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 6.17h， 以67%的产率得到[6-(2,3,4,5,6-Pentafluorobenzoyl)oxy-8-[[4-(trifluoromethyl)phenyl]methyl]-3-pentacyclo[6.6.6.02,7.09,14.015,20]icosa-2,4,6,9,11,13,15,17,19-nonaenyl] 2,3,4,5,6-pentafluorobenzoate
  参考文献：
  名称：

  芳香相互作用中电荷转移的阈值？π-堆积相互作用的定量研究

  摘要：

  已使用三萜烯衍生的分子构象报告分子定量研究了平行取代结构中取代的芳烃之间的吸引力相互作用。在强供体和受体之间相互作用的模型中观察到电荷转移带。取代基对芳族相互作用强度的影响遵循强电子缺乏型芳烃和轻度扰动芳烃的相反趋势。具有强电子给体和受体的模型的相互作用自由能在哈米特图中不遵循线性关系。仅静电模型不能解决自由能取代基图的非线性问题。

  DOI：

  10.1021/jo051808a
• 作为产物：
  描述：

  对三氟甲基苯甲醛 在 sodium tetrahydroborate 、 正丁基锂 、 potassium acetate 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 69.08h， 生成 9-(4-trifluoromethylbenzyl)-1,4-dihydroxytriptycene
  参考文献：
  名称：

  The Strength of Parallel-Displaced Arene−Arene Interactions in Chloroform

  摘要：

  Triptycene-derived compounds have been prepared to serve as conformational equilibrium reporters for direct measurements of arene-arene interactions in the parallel-displaced orientation. A series of such compounds bearing arenes with different substituents were synthesized, and the ratios of the syn and anti conformers were determined by variable-temperature NMR spectroscopy. The syn conformer allows attached arenes to interact with each other while the anti conformer does not. The free energies derived from the syn/anti ratios in chloroform range from slightly positive (0.2 kcal/mol) to considerably negative (-0.98 kcal mol) values. The interactions between the arenes bearing electron-donating groups (EDG) are either negligible or slightly repulsive, while the interactions between arenes bearing electron-withdrawing groups (EWG) are attractive. Intermediate free energy values are obtained for those compounds bearing arenes with one EDG and one EWG.

  DOI：

  10.1021/jo050049t

文献信息

• A Threshold for Charge Transfer in Aromatic Interactions? A Quantitative Study of π-Stacking Interactions
  作者：Benjamin W. Gung、Mehul Patel、Xiaowen Xue

  DOI：10.1021/jo051808a

  日期：2005.12.1

  Attractive interactions between substituted arenes in the parallel displaced configuration have been quantitatively studied using triptycene-derived molecular conformational reporters. Charge-transfer bands are observed for models where the interactions are between strong donor and acceptors. Substituent effects on the strength of the aromatic interaction follow opposite trends for strongly electron-deficient

  已使用三萜烯衍生的分子构象报告分子定量研究了平行取代结构中取代的芳烃之间的吸引力相互作用。在强供体和受体之间相互作用的模型中观察到电荷转移带。取代基对芳族相互作用强度的影响遵循强电子缺乏型芳烃和轻度扰动芳烃的相反趋势。具有强电子给体和受体的模型的相互作用自由能在哈米特图中不遵循线性关系。仅静电模型不能解决自由能取代基图的非线性问题。
• The Strength of Parallel-Displaced Arene−Arene Interactions in Chloroform
  作者：Benjamin W. Gung、Xiaowen Xue、Hans J. Reich

  DOI：10.1021/jo050049t

  日期：2005.4.1

  Triptycene-derived compounds have been prepared to serve as conformational equilibrium reporters for direct measurements of arene-arene interactions in the parallel-displaced orientation. A series of such compounds bearing arenes with different substituents were synthesized, and the ratios of the syn and anti conformers were determined by variable-temperature NMR spectroscopy. The syn conformer allows attached arenes to interact with each other while the anti conformer does not. The free energies derived from the syn/anti ratios in chloroform range from slightly positive (0.2 kcal/mol) to considerably negative (-0.98 kcal mol) values. The interactions between the arenes bearing electron-donating groups (EDG) are either negligible or slightly repulsive, while the interactions between arenes bearing electron-withdrawing groups (EWG) are attractive. Intermediate free energy values are obtained for those compounds bearing arenes with one EDG and one EWG.