2,8-dimethoxydibenzo[c,e][1,2]oxaborinin-6-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,8-dimethoxydibenzo[c,e][1,2]oxaborinin-6-ol
• 英文别名: 6-Hydroxy-3,9-dimethoxybenzo[c][1,2]benzoxaborinine；6-hydroxy-3,9-dimethoxybenzo[c][1,2]benzoxaborinine
• 化学式: C₁₄H₁₃BO₄
• 分子量: 256.066
• InChiKey: AOUSUDYXZQURJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.45
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,8-dimethoxydibenzo[c,e][1,2]oxaborinin-6-ol 在 2-双环己基膦-2',6'-二甲氧基联苯 、 吡啶 、 potassium phosphate 、 palladium diacetate 、 三溴化硼 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 72.34h， 生成
  参考文献：
  名称：

  Enhanced Helical Folding of ortho-Phenylenes through the Control of Aromatic Stacking Interactions

  摘要：

  The ortho-phenylenes are a simple class of foldamers, with the formation of helices driven by offset aromatic stacking interactions parallel to the helical axis. For the majority of reported o-phenylene oligomers, the perfectly folded conformer comprises perhaps 5075% of the total population. Given the hundreds or thousands of possible conformers for even short oligomers, this distribution represents a substantial bias toward the folded state. However, next-generation o-phenylenes with better folding properties are needed if these structures are to be exploited as functional units within more complex architectures. Here, we report several new series of o-phenylene oligomers, varying both the nature and orientation of the substituents on every repeat unit. The conformational behavior was probed using a combination of NMR spectroscopy, DFT calculations, and X-ray crystallography. We find that increasing the electron-withdrawing character of the substituents gives oligomers with substantially improved folding properties. With moderately electron-withdrawing groups (acetoxy), we observe >90% of the perfectly folded conformer, and stronger electron withdrawing groups (triflate, cyano) give oligomers for which misfolded states are undetectable by NMR. The folding of these oligomers is only weakly solvent-dependent. General guidelines for the assessment of o-phenylene folding by NMR and UVvis spectroscopy are also discussed.

  DOI：

  10.1021/ja509902m
• 作为产物：
  描述：

  2-溴-5-甲氧基苯基硼酸 在 四(三苯基膦)钯 、 正丁基锂 、 4-甲基苯磺酸吡啶 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 27.55h， 生成 2,8-dimethoxydibenzo[c,e][1,2]oxaborinin-6-ol
  参考文献：
  名称：

  Enhanced Helical Folding of ortho-Phenylenes through the Control of Aromatic Stacking Interactions

  摘要：

  The ortho-phenylenes are a simple class of foldamers, with the formation of helices driven by offset aromatic stacking interactions parallel to the helical axis. For the majority of reported o-phenylene oligomers, the perfectly folded conformer comprises perhaps 5075% of the total population. Given the hundreds or thousands of possible conformers for even short oligomers, this distribution represents a substantial bias toward the folded state. However, next-generation o-phenylenes with better folding properties are needed if these structures are to be exploited as functional units within more complex architectures. Here, we report several new series of o-phenylene oligomers, varying both the nature and orientation of the substituents on every repeat unit. The conformational behavior was probed using a combination of NMR spectroscopy, DFT calculations, and X-ray crystallography. We find that increasing the electron-withdrawing character of the substituents gives oligomers with substantially improved folding properties. With moderately electron-withdrawing groups (acetoxy), we observe >90% of the perfectly folded conformer, and stronger electron withdrawing groups (triflate, cyano) give oligomers for which misfolded states are undetectable by NMR. The folding of these oligomers is only weakly solvent-dependent. General guidelines for the assessment of o-phenylene folding by NMR and UVvis spectroscopy are also discussed.

  DOI：

  10.1021/ja509902m