9-Phenylphosphindolo[2,3-c]pyridine 9-oxide | 1312012-54-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 9-Phenylphosphindolo[2,3-c]pyridine 9-oxide
• 英文别名: 9-phenylphosphindolo[2,3-c]pyridine 9-oxide
• CAS: 1312012-54-6
• 化学式: C₁₇H₁₂NOP
• 分子量: 277.262
• InChiKey: CKHIEPYIQIDDAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 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：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  potassium tetrachloroplatinate(II) 、 9-Phenylphosphindolo[2,3-c]pyridine 9-oxide 以 乙醇 、 水 为溶剂， 以62%的产率得到
  参考文献：
  名称：

  Azadibenzophospholes: Functional Building Blocks with Pronounced Electron-Acceptor Character

  摘要：

  A series of azadibenzophospholes with varying location of the nitrogen center has been synthesized and comprehensively characterized. In the context of the study, suitably brominated phenylpyridine precursors were accessed via Suzuki-Miyaura cross-coupling for the first time. Despite being nonfluorescent, X-ray crystallographic studies of two azadibenzophosphole oxides revealed planar conjugated scaffolds with high degree of pi-conjugation. The P-oxidized species were found to show desirable reversible reduction features that support promising electron-accepting properties of the materials. The presence of the nitrogen as well as phosphorus centers within the scaffold allowed for further functionalization with transition metals, as well as methyl groups that result in altered absorption and redox features for the materials. Subsequent bromination of the scaffold selectively occurred at the exocydic P-phenyl group, as confirmed via X-ray crystallography. This halogenation allowed for further modification of the system via catalytic cross-coupling with pyridine.

  DOI：

  10.1021/ic200951x
• 作为产物：
  描述：

  3-溴-4-碘吡啶 在 四(三苯基膦)钯 、 双氧水 、 叔丁基锂 、 potassium carbonate 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醚 、 氯仿 、 水 、 正戊烷 为溶剂， 反应 75.0h， 生成 9-Phenylphosphindolo[2,3-c]pyridine 9-oxide
  参考文献：
  名称：

  Azadibenzophospholes: Functional Building Blocks with Pronounced Electron-Acceptor Character

  摘要：

  A series of azadibenzophospholes with varying location of the nitrogen center has been synthesized and comprehensively characterized. In the context of the study, suitably brominated phenylpyridine precursors were accessed via Suzuki-Miyaura cross-coupling for the first time. Despite being nonfluorescent, X-ray crystallographic studies of two azadibenzophosphole oxides revealed planar conjugated scaffolds with high degree of pi-conjugation. The P-oxidized species were found to show desirable reversible reduction features that support promising electron-accepting properties of the materials. The presence of the nitrogen as well as phosphorus centers within the scaffold allowed for further functionalization with transition metals, as well as methyl groups that result in altered absorption and redox features for the materials. Subsequent bromination of the scaffold selectively occurred at the exocydic P-phenyl group, as confirmed via X-ray crystallography. This halogenation allowed for further modification of the system via catalytic cross-coupling with pyridine.

  DOI：

  10.1021/ic200951x

文献信息

• Palladium-Catalyzed Direct Synthesis of Phosphole Derivatives from Triarylphosphines through Cleavage of Carbon-Hydrogen and Carbon-Phosphorus Bonds
  作者：Katsuaki Baba、Mamoru Tobisu、Naoto Chatani

  DOI：10.1002/anie.201307115

  日期：2013.11.4

  (Phosp)hole in one: A palladium‐catalyzed synthesis for directly assembling phosphole skeletons from triarylphosphines through CH and CP bond cleavage was developed. This approach overcomes several of the limitations of the so far reported methods. Phospholes bearing a range of functionalities (including Br, F, CO2Me, Ac, and CN) and an array of fused rings (naphthalenes, anthracenes, furans, and

  在一个（Phosp）孔：一个钯催化合成的用于从至C三芳基膦直接组装磷杂环骨架 H和13 C  P键裂解被开发。这种方法克服了迄今为止报道的方法的一些局限性。可以容易地合成具有一系列功能性（包括Br，F，CO 2 Me，Ac和CN）的磷脂和一系列稠环（萘，蒽，呋喃和吡咯）。
• Azadibenzophospholes: Functional Building Blocks with Pronounced Electron-Acceptor Character
  作者：Stefan Durben、Thomas Baumgartner

  DOI：10.1021/ic200951x

  日期：2011.7.18

  A series of azadibenzophospholes with varying location of the nitrogen center has been synthesized and comprehensively characterized. In the context of the study, suitably brominated phenylpyridine precursors were accessed via Suzuki-Miyaura cross-coupling for the first time. Despite being nonfluorescent, X-ray crystallographic studies of two azadibenzophosphole oxides revealed planar conjugated scaffolds with high degree of pi-conjugation. The P-oxidized species were found to show desirable reversible reduction features that support promising electron-accepting properties of the materials. The presence of the nitrogen as well as phosphorus centers within the scaffold allowed for further functionalization with transition metals, as well as methyl groups that result in altered absorption and redox features for the materials. Subsequent bromination of the scaffold selectively occurred at the exocydic P-phenyl group, as confirmed via X-ray crystallography. This halogenation allowed for further modification of the system via catalytic cross-coupling with pyridine.