C6H8C2P(2-pyridyl)2(phenyl) | 222042-11-7

• 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: C6H8C2P(2-pyridyl)2(phenyl)
• 英文别名: 2,5-bis(2-pyridyl)-1-phenylphosphole；2-(2-Phenyl-3-pyridin-2-YL-4,5,6,7-tetrahydro-2H-isophosphindol-1-YL)pyridine；2-(2-phenyl-3-pyridin-2-yl-4,5,6,7-tetrahydroisophosphindol-1-yl)pyridine
• CAS: 222042-11-7
• 化学式: C₂₄H₂₁N₂P
• 分子量: 368.418
• InChiKey: GSKNNHAAFLPYHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 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：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  C6H8C2P(2-pyridyl)2(phenyl) 在 双(三甲基硅基)过氧化物 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以95%的产率得到2-Phenyl-1,3-dipyridin-2-yl-4,5,6,7-tetrahydroisophosphindole 2-oxide
  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
• 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 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 26.0h， 生成 C6H8C2P(2-pyridyl)2(phenyl)
  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

• Enantiomerically Pure P,N Chelates Based on Phospholene Rings: Palladium Complexes and Catalytic Applications in Allylic Substitution
  作者：François Leca、Fernando Fernández、Guillermo Muller、Christophe Lescop、Régis Réau、Montserrat Gómez

  DOI：10.1002/ejic.200900892

  日期：2009.12

  The synthesis of optically pure 2-pyridylphospholene ligands by diastereomeric resolution of PdII complexes, bearing the corresponding racemic P,N ligand and (R)-α-methylbenzylamine, by means of fractional crystallisation is described. A full coordination study of palladium complexes containing 2-pyridylphospholene and the corresponding phosphole ligands, both in solution (by means of NMR spectroscopy)

  描述了通过 PdII 配合物的非对映异构拆分合成光学纯的 2-吡啶基磷烯配体, 带有相应的外消旋 P,N 配体和 (R)-α-甲基苄胺, 通过分步结晶。进行了包含 2-吡啶基磷烯和相应磷光体配体的钯配合物在溶液中（通过 NMR 光谱）和固态（通过 X 射线衍射）的完整配位研究。这些配体在 Pd 催化的外消旋底物（rac-3-acetoxy-1,3-diphenyl-1-propene 和 rac-3-acetoxy-1-cyclohexene）和 (E)-3-acetoxy-1 的烯丙基取代中进行了评估-苯基-1-丙烯。对钯烯丙基中间体进行了建模研究，以证明用 2-吡啶基磷烯配体观察到的不对称诱导是正确的。 (© Wiley-VCH Verlag GmbH &
• Can Coordination‐Driven Supramolecular Self‐Assembly Reactions Be Conducted from Fully Aliphatic Linkers?
  作者：Mehdi Elsayed Moussa、Sloane Evariste、Barbara Krämer、Régis Réau、Manfred Scheer、Christophe Lescop

  DOI：10.1002/anie.201709119

  日期：2018.1.15

  The reaction between a preassembled CuI bimetallic molecular clip with a short intermetallic distance and a series of fully aliphatic cyano‐capped ditopic linkers with increasing lengths was investigated. It is shown that, depending on the length of the ditopic linkers, the rational design of unprecedented supramolecular compact metallacycles containing fully aliphatic walls is possible. The specific

  预组装Cu I之间的反应研究了金属间距离短的双金属分子夹和一系列长度增加的全脂族氰基封端的二位连接体。结果表明，根据双位连接体的长度，合理设计包含完全脂族壁的前所未有的超分子致密金属环可能是可行的。所使用的分子夹的特定的预先组织的分子排列有利于稳定交联剂伦敦分散体相互作用，这允许随着交联剂长度的增加而选择性地形成离散的致密金属环，而以一维配位聚合物为代价。完全脂肪族的氰基封端的连接基与另外两种预组装的Cu I的反应证明了这种方法的通用性。 双金属分子夹也具有较短的金属间距离。
• 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。
• METHOD FOR SELECTIVE PALLADIUM-CATALYZED TELOMERIZATION OF SUBSTITUTED DIENES
  申请人：INTERNATIONAL FLAVORS & FRAGRANCES INC.

  公开号：US20170275235A1

  公开（公告）日：2017-09-28

  A method for the selective synthesis of a tail-to-head, or a head-to-head, or a tail-to-tail telomer from an unsymmetrical diene by polymerizing the diene in the presence of [Pd(C 3 H 5 )COD]BF 4 and dicyclohexyl-[1-(2,4,6-trimethylphenyl)imidazol-2-yl]phosphane, Pd(OAc) 2 and triphenylphosphine, or [Pd(C 3 H 5 )COD]BF 4 and tris(2,4-di-tert-butylphenyl)phosphite in combination with a polar protic alcohol, an acidic polar protic alcohol, a polar aprotic ether, or a non-polar aprotic hydrocarbon is provided.

  提供了一种从非对称二烯通过在[Pd(C3H5)COD]BF4和二环己基-[1-(2,4,6-三甲基苯基)咪唑-2-基]膦烷，Pd(OAc)2和三苯基膦，或[Pd(C3H5)COD]BF4和三(2,4-二叔丁基苯基)磷酸酯的存在下，通过在极性质子醇，酸性极性质子醇，极性无水醚或非极性无水碳氢化合物中聚合二烯的方法，选择性地合成尾-头，头-头或尾-尾缩聚物。
• 2-Pyridyl-2-phospholenes: New P,N ligands for the palladium-catalyzed isoprene telomerization
  作者：F LECA、R REAU

  DOI：10.1016/j.jcat.2006.01.010

  日期：2006.3.10

  ligands for the palladium-catalyzed telomerization of isoprene with diethylamine. Good selectivities for the tail-to-head or tail-to-tail aminoterpenes are achieved on optimization of the ligand substituents and of the reaction conditions, such as the nature of the catalyst precursor and of the solvent. Moreover, excellent catalytic activities are achieved on photochemical activation or addition of acidic

  2-（2-吡啶基）-2-膦烯是异戊二烯与二乙胺在钯催化的端粒化反应中有效的配体。通过优化配体取代基和反应条件，例如催化剂前体和溶剂的性质，可以实现尾对头或尾对尾氨基萜的良好选择性。此外，在光化学活化或添加酸性助催化剂时，可获得优异的催化活性。