2-(1-hydroxypropyl)-1,10-phenanthroline | 691014-07-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: 2-(1-hydroxypropyl)-1,10-phenanthroline
• 英文别名: 1-(1,10-Phenanthrolin-2-yl)propan-1-ol；1-(1,10-phenanthrolin-2-yl)propan-1-ol
• CAS: 691014-07-0
• 化学式: C₁₅H₁₄N₂O
• 分子量: 238.289
• InChiKey: MHYAMUSZFYCNPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1-hydroxypropyl)-1,10-phenanthroline 在 吡啶 、 4-二甲氨基吡啶 、 samarium diiodide 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 反应 17.33h， 生成 2-propyl-1,10-phenanthroline
  参考文献：
  名称：

  Samarium-Promoted Coupling of 1,10-Phenanthroline with Carbonyl Compounds for Synthesis of New Ligands

  摘要：

  1,10-Phenanthroline reacts with aldehydes and ketones in the presence of samarium diiodide to produce 2-(1-hydroxyalkyl)-1,10-phenanthrolines. The hydroxyalkyl substituent can be functionalized in numerous ways or removed to permit further ligand variation. The carbonyl coupling reaction can also be repeated to provide 2,9-disubstituted phenanthrolines. Taken together, these operations provide ready access to a large number of phenanthroline derivatives to serve as ligand libraries for catalyst exploration.

  DOI：

  10.1021/jo0303416
• 作为产物：
  描述：

  1,10-菲罗啉 、 丙醛 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以94%的产率得到2-(1-hydroxypropyl)-1,10-phenanthroline
  参考文献：
  名称：

  Samarium-Promoted Coupling of 1,10-Phenanthroline with Carbonyl Compounds for Synthesis of New Ligands

  摘要：

  1,10-Phenanthroline reacts with aldehydes and ketones in the presence of samarium diiodide to produce 2-(1-hydroxyalkyl)-1,10-phenanthrolines. The hydroxyalkyl substituent can be functionalized in numerous ways or removed to permit further ligand variation. The carbonyl coupling reaction can also be repeated to provide 2,9-disubstituted phenanthrolines. Taken together, these operations provide ready access to a large number of phenanthroline derivatives to serve as ligand libraries for catalyst exploration.

  DOI：

  10.1021/jo0303416

文献信息

• Samarium-Promoted Coupling of Pyridine-Based Heteroaryl Analogues of Benzylic Acetates with Carbonyl Compounds
  作者：Jeremy A. Weitgenant、Jonathan D. Mortison、Paul Helquist

  DOI：10.1021/ol050944z

  日期：2005.8.1

  [GRAPHICS]2-Substituted pyridine, quinoline, isoquinoline, bipyridine, and 1,10-phenanthroline analogues of benzylic acetates undergo Sml(2)-promoted coupling with aldehydes and ketones to afford (2-hydroxyalkyl)heteroaromatics.
• Samarium-Promoted Coupling of 1,10-Phenanthroline with Carbonyl Compounds for Synthesis of New Ligands
  作者：Jeremy A. Weitgenant、Jonathan D. Mortison、David J. O'Neill、Brendan Mowery、Anders Puranen、Paul Helquist

  DOI：10.1021/jo0303416

  日期：2004.4.1

  1,10-Phenanthroline reacts with aldehydes and ketones in the presence of samarium diiodide to produce 2-(1-hydroxyalkyl)-1,10-phenanthrolines. The hydroxyalkyl substituent can be functionalized in numerous ways or removed to permit further ligand variation. The carbonyl coupling reaction can also be repeated to provide 2,9-disubstituted phenanthrolines. Taken together, these operations provide ready access to a large number of phenanthroline derivatives to serve as ligand libraries for catalyst exploration.