2,9-diacetyl-1,10-phenanthroline | 864510-41-8

• 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: 2,9-diacetyl-1,10-phenanthroline
• 英文别名: 1,1'-(1,10-Phenanthroline-2,9-diyl)diethanone；1-(9-acetyl-1,10-phenanthrolin-2-yl)ethanone
• CAS: 864510-41-8
• 化学式: C₁₆H₁₂N₂O₂
• 分子量: 264.283
• InChiKey: GKQUHQZSJKDCPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  59.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,9-diacetyl-1,10-phenanthroline 、 2-氨基-3-吡啶甲醛 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 以77%的产率得到2,9-di(1,8-naphthyrid-2-yl)-1,10-phenanthroline
  参考文献：
  名称：

  Synthetic Approaches to Polypyridyl Bridging Ligands with Proximal Multidentate Binding Sites

  摘要：

  A series of 12 bridging ligands was prepared. These ligands include a central linker appended to two 1,8-naphthyrid-2-yl or two 1,10-phenanthrolin-2-yl units. The linkers include pyridazin-3.6-diyl, 1,8-naphthyrid-2,7-diyl, 2,2'-bipyrid-6,6'-diyl, 1, 10-phenanthrolin-2,9-diyl, 1,2-di(2'-pyrid-6'-yl)ethyne, and 3,6-di(2'-pyrid-6'-yl)pyridazine. The ligands were synthesized from the diacetyl derivative of the central linker by a Friedlander condensation with either 2-aminonicotinaldehyde or 8-amino-7-quinolinecarbaldehyde. The precursor diacetyl derivatives were, in turn, prepared by pathways involving Stille and Sonogashira couplings. Examination of the electronic absorption spectra of the bridging ligands shows the strongest correlation to be between pairs of ligands having the same central linker. Complexation studies will follow.

  DOI：

  10.1021/jo051937r
• 作为产物：
  描述：

  2,9-二氯-1,10-菲罗啉 在 bis(triphenylphosphine)palladium(II)-chloride 盐酸 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 80.0h， 生成 2,9-diacetyl-1,10-phenanthroline
  参考文献：
  名称：

  Synthetic Approaches to Polypyridyl Bridging Ligands with Proximal Multidentate Binding Sites

  摘要：

  A series of 12 bridging ligands was prepared. These ligands include a central linker appended to two 1,8-naphthyrid-2-yl or two 1,10-phenanthrolin-2-yl units. The linkers include pyridazin-3.6-diyl, 1,8-naphthyrid-2,7-diyl, 2,2'-bipyrid-6,6'-diyl, 1, 10-phenanthrolin-2,9-diyl, 1,2-di(2'-pyrid-6'-yl)ethyne, and 3,6-di(2'-pyrid-6'-yl)pyridazine. The ligands were synthesized from the diacetyl derivative of the central linker by a Friedlander condensation with either 2-aminonicotinaldehyde or 8-amino-7-quinolinecarbaldehyde. The precursor diacetyl derivatives were, in turn, prepared by pathways involving Stille and Sonogashira couplings. Examination of the electronic absorption spectra of the bridging ligands shows the strongest correlation to be between pairs of ligands having the same central linker. Complexation studies will follow.

  DOI：

  10.1021/jo051937r

文献信息

• Chemoselective, osmium-free, dihydroxylation/oxidative cleavage of heteroaryl isoprenes by a contemporary Malaprade reaction
  作者：Zachary Z. Gulledge、Connor C. Pinson、Alexander M. Stovall、Fortune O. Dzeagu、Jesse D. Carrick

  DOI：10.1039/d2ob01643e

  日期：——

  oxidative-cleavage strategies, frequently result in diminished performance over carbon-based arenes. In this work we present the development and application of an oxidative cleavage reaction of various pyridinyl isoprenes towards accessing the downstream methyl ketone for utilization in advanced cyclizations for the preparation of soft-N-donor complexant scaffolds. This efficient protocol parallels the principles

  甲基酮是构建先进杂芳基支架和系统的核心合成构件。包括氧化环化策略在内的反应通常取决于对这种普遍存在的部分的有效访问。在芳烃的背景下，利用马尔科夫尼科夫水合/氧化或 C-C π 键的氧化裂解的标准方法通常可以提供令人满意的性能。然而，当底物包含缺电子杂芳基核心时，传统的 Malaprade 反应和相关的氧化裂解策略通常会导致性能低于碳基芳烃。在这项工作中，我们介绍了各种吡啶基异戊二烯的氧化裂解反应的开发和应用，以获取下游甲基酮，用于高级环化以制备软 N 供体络合剂支架。这种高效的协议通过交换 KMnO 与绿色化学的原理平行4用于有毒的 OsO 4，并为最终用户提供了一种高效、更环保的选择，使用高锰酸钾和过碘酸钠作为协同有效的氧化裂解系统，在一小时的反应时间内获得杂芳基甲基酮。广泛的底物范围定义了获得简单和先进的杂芳基甲基酮的途径。本文描述了方法开发、优化、底物范围、初步机制观察和放大反应。
• Synthetic Approaches to Polypyridyl Bridging Ligands with Proximal Multidentate Binding Sites
  作者：Ruifa Zong、Dong Wang、Richard Hammitt、Randolph P. Thummel

  DOI：10.1021/jo051937r

  日期：2006.1.1

  A series of 12 bridging ligands was prepared. These ligands include a central linker appended to two 1,8-naphthyrid-2-yl or two 1,10-phenanthrolin-2-yl units. The linkers include pyridazin-3.6-diyl, 1,8-naphthyrid-2,7-diyl, 2,2'-bipyrid-6,6'-diyl, 1, 10-phenanthrolin-2,9-diyl, 1,2-di(2'-pyrid-6'-yl)ethyne, and 3,6-di(2'-pyrid-6'-yl)pyridazine. The ligands were synthesized from the diacetyl derivative of the central linker by a Friedlander condensation with either 2-aminonicotinaldehyde or 8-amino-7-quinolinecarbaldehyde. The precursor diacetyl derivatives were, in turn, prepared by pathways involving Stille and Sonogashira couplings. Examination of the electronic absorption spectra of the bridging ligands shows the strongest correlation to be between pairs of ligands having the same central linker. Complexation studies will follow.