9-Phenylphosphindolo[2,3-b]pyridine | 1312012-30-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 9-Phenylphosphindolo[2,3-b]pyridine
• 英文别名: 9-phenylphosphindolo[2,3-b]pyridine
• CAS: 1312012-30-8
• 化学式: C₁₇H₁₂NP
• 分子量: 261.263
• InChiKey: DQZWBNOBUGCELX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 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：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  9-Phenylphosphindolo[2,3-b]pyridine 在 N-溴代丁二酰亚胺(NBS) 、 硫酸 、 双氧水 、 三氟乙酸 作用下， 以 氯仿 、 水 为溶剂， 反应 2.0h， 生成
  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：

  2-溴苯基硼酸 在 四(三苯基膦)钯 、 叔丁基锂 、 三溴化磷 、 potassium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 四氢呋喃 、 乙醚 、 水 、 正戊烷 为溶剂， 反应 113.0h， 生成 9-Phenylphosphindolo[2,3-b]pyridine
  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

• 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.