1-phenyl-2,5-(2-pyridyl)thioxophosphole | 222042-08-2

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 1-phenyl-2,5-(2-pyridyl)thioxophosphole
• 英文别名: 2-(2-Phenyl-3-pyridin-2-yl-2-sulfanylidene-4,5,6,7-tetrahydroisophosphindol-1-yl)pyridine
• CAS: 222042-08-2
• 化学式: C₂₄H₂₁N₂PS
• 分子量: 400.484
• InChiKey: CMPBBSBSRCOWPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  57.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-phenyl-2,5-(2-pyridyl)thioxophosphole 以 四氢呋喃 为溶剂， 反应 48.0h， 以100%的产率得到2-(2-Phenyl-3-pyridin-2-yl-2-sulfanylidene-1,4,5,6-tetrahydroisophosphindol-1-yl)pyridine
  参考文献：
  名称：

  An aromatic–antiaromatic switch in P-heteroles. A small change in delocalisation makes a big reactivity difference

  摘要：

  通过氧化磷原子，可以将磷环的低芳香性转变为低反芳香性。这种分散模式的微妙变化大大改变了这些杂环的化学特性。

  DOI：

  10.1039/b516836h
• 作为产物：
  描述：

  1,7-辛二炔 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 正丁基锂 、 二氯二茂锆 、 sulfur 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 62.0h， 生成 1-phenyl-2,5-(2-pyridyl)thioxophosphole
  参考文献：
  名称：

  Phosphole-Containing π-Conjugated Systems: From Model Molecules to Polymer Films on Electrodes

  摘要：

  Two series of 2.5-dipyridyl and 2.5-dithienylphosphole derivatives containing sigma (3)- or sigma (4)-P atoms were prepared. and their optical (UV/Vis absorption, fluorescence spectra) and electrochemical properties were systematically evaluated. These physical properties depend mainly on the natures of the 2.5-substituents and of the phosphorus moiety, and they revealed that these compounds contain extended pi- conjugated systems. Structure -property relationships were established on the basis of these experimental data and ab initio calculations on the parent molecules. The limited aromatic character and low-lying LUMO of the phosphole ring appear to be crucial for achieving a highly delocalised pi system. Electrooxidation of 2,5-dithienylphosphole derivatives affords electroactive films with low optical band gaps. As observed for the corresponding monomers, the optical and electrochemical properties of the polymers can be varied over a wide range by modifying the nature of the phosphorus moiety.

  DOI：

  10.1002/1521-3765(20011001)7:19<4222::aid-chem4222>3.0.co;2-3

文献信息

• Syntheses of CuI polymetallic assemblies from reaction of ligands bearing the 2,5-bis(2-pyridyl)phosphole fragment with CuII precursors
  作者：Mehdi El Sayed Moussa、Fabian Friess、Wenting Shen、Muriel Hissler、Régis Réau、Christophe Lescop

  DOI：10.1039/c3cc42955e

  日期：——

  Upon reaction with ligands A, 1 and 3 bearing the 2,5-bis(2-pyridyl)phosphole fragment, an unexpected conversion of Cu(II) metal centers to Cu(I) centers is observed affording either bimetallic complexes bearing a bridging phosphane coordination mode or hexametallic metallacycles.

  与带有2,5-双（2-吡啶基）磷脂片段的配体A，1和3反应后，观察到Cu（II）金属中心向Cu（I）中心的意外转化，从而得到带有桥联膦的双金属配合物配位模式或六金属金属环。
• 2,5-Di(2-pyridyl)phospholes: model compounds for the engineering of π-conjugated donor–acceptor co-oligomers with a chemically tunable HOMO–LUMO gap
  作者：Caroline Hay、Delphine Le Vilain、Valérie Deborde、Régis Réau、Loïc Toupet

  DOI：10.1039/a808408d

  日期：——

  2,5-Di(2-pyridyl)phospholes possess an extended π-conjugated system with a charge transfer structure; high yielding chemical modifications involving the phosphorus atom allow fine tuning of the HOMO–LUMO gap.

  2,5-二(2-吡啶基)磷烯具有扩展的π-共轭系统和电荷转移结构；涉及磷原子的高产率化学修饰允许对HOMO-LUMO能隙进行精细调节。