2-(2',6'-difluorophenyl)-1,10-phenanthroline | 1272029-49-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-(2',6'-difluorophenyl)-1,10-phenanthroline
• 英文别名: 2-(o-difluorophenyl)-1,10-phenanthroline；odfp-phen；2-(2,6-Difluorophenyl)-1,10-phenanthroline；2-(2,6-difluorophenyl)-1,10-phenanthroline
• CAS: 1272029-49-8
• 化学式: C₁₈H₁₀F₂N₂
• 分子量: 292.288
• InChiKey: UHSQGUUYAWIARO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2',6'-difluorophenyl)-1,10-phenanthroline 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 生成 3-Fluoro-2-(1,10-phenanthrolin-2-yl)phenolate;palladium(2+);acetate
  参考文献：
  名称：

  Oxidatively Resistant Ligands for Palladium-Catalyzed Aerobic Alcohol Oxidation

  摘要：

  The complex [(neocuproine)Pd(OAc)](2)[OTf](2) (1) catalyzes the aerobic oxidation of 2-heptanol at room temperature, but Competitive ligand oxidation leads to low catalyst lifetimes. In an effort to mitigate the oxidative degradation of the ligand, a variety of Pd complexes ligated by fluorinated phenanthrolines (bis-2,9-(trifluoromethyl)-1,10-phenanthroline (btfm-phen), 4-methyl-2-(trifluoromethyl)-1,10-phenanthroline (tfmm-phen), and 2-(o-difluoropheny1)-1,10-phenanthroline (odfp-phen)) were prepared and tested. Active catalyst precursors were generated by in situ conproportionation of (N- N)Pd(OAc)(2) and [(N-N)Pd(NCCH3)(2)[OTf](2). Pd complexes derived from tfmm-phen catalyzed the aerobic oxidation of 2-heptanol at room temperature with up to 22 turnovers, nearly double that of 1.

  DOI：

  10.1021/om101037k
• 作为产物：
  描述：

  2,6-二氟苯乙酮 、 8-胺基-7-醛基喹啉 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 15.0h， 以58%的产率得到2-(2',6'-difluorophenyl)-1,10-phenanthroline
  参考文献：
  名称：

  Oxidatively Resistant Ligands for Palladium-Catalyzed Aerobic Alcohol Oxidation

  摘要：

  The complex [(neocuproine)Pd(OAc)](2)[OTf](2) (1) catalyzes the aerobic oxidation of 2-heptanol at room temperature, but Competitive ligand oxidation leads to low catalyst lifetimes. In an effort to mitigate the oxidative degradation of the ligand, a variety of Pd complexes ligated by fluorinated phenanthrolines (bis-2,9-(trifluoromethyl)-1,10-phenanthroline (btfm-phen), 4-methyl-2-(trifluoromethyl)-1,10-phenanthroline (tfmm-phen), and 2-(o-difluoropheny1)-1,10-phenanthroline (odfp-phen)) were prepared and tested. Active catalyst precursors were generated by in situ conproportionation of (N- N)Pd(OAc)(2) and [(N-N)Pd(NCCH3)(2)[OTf](2). Pd complexes derived from tfmm-phen catalyzed the aerobic oxidation of 2-heptanol at room temperature with up to 22 turnovers, nearly double that of 1.

  DOI：

  10.1021/om101037k

文献信息

• Oxidatively Resistant Ligands for Palladium-Catalyzed Aerobic Alcohol Oxidation
  作者：David M. Pearson、Nicholas R. Conley、Robert M. Waymouth

  DOI：10.1021/om101037k

  日期：2011.3.28

  The complex [(neocuproine)Pd(OAc)](2)[OTf](2) (1) catalyzes the aerobic oxidation of 2-heptanol at room temperature, but Competitive ligand oxidation leads to low catalyst lifetimes. In an effort to mitigate the oxidative degradation of the ligand, a variety of Pd complexes ligated by fluorinated phenanthrolines (bis-2,9-(trifluoromethyl)-1,10-phenanthroline (btfm-phen), 4-methyl-2-(trifluoromethyl)-1,10-phenanthroline (tfmm-phen), and 2-(o-difluoropheny1)-1,10-phenanthroline (odfp-phen)) were prepared and tested. Active catalyst precursors were generated by in situ conproportionation of (N- N)Pd(OAc)(2) and [(N-N)Pd(NCCH3)(2)[OTf](2). Pd complexes derived from tfmm-phen catalyzed the aerobic oxidation of 2-heptanol at room temperature with up to 22 turnovers, nearly double that of 1.