Diphenyl-2-pyridylmethyl-phosphinoxid | 13119-80-7

• 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: Diphenyl-2-pyridylmethyl-phosphinoxid
• 英文别名: 2-[(Diphenylphosphoryl)methyl]pyridine；2-(diphenylphosphorylmethyl)pyridine
• CAS: 13119-80-7
• 化学式: C₁₈H₁₆NOP
• 分子量: 293.305
• InChiKey: LSPLDENUOBBLOB-UHFFFAOYSA-N

物化性质

• 熔点：
  133-134 °C
• 沸点：
  431.2±28.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  Diphenyl-2-pyridylmethyl-phosphinoxid 在 双氧水 作用下， 以 溶剂黄146 为溶剂， 反应 12.0h， 以62.5%的产率得到(α-pyridylmethyl)diphenylphosphine oxide N-oxide
  参考文献：
  名称：

  Phosphorylmethylpyridines and their N-oxides: Synthesis and equilibrium CH-acidity

  摘要：

  Certain phosphorylmethylpyridines and their N-oxides were synthesized, which are of interest as extractants and complex-forming agents. Their equilibrium CH-acidity with reference to 9-phenylfluorene (K+ counterion) was studied by the indicator method in dimethyl sulfoxide. The acidifying action of a series of pyridine groupings was characterized by means of sigma-C- values.

  DOI：

  10.1007/bf00958579
• 作为产物：
  描述：

  二苯基(吡啶-2-基甲基)膦 在 双氧水 作用下， 以 丙酮 为溶剂， 反应 1.0h， 生成 Diphenyl-2-pyridylmethyl-phosphinoxid
  参考文献：
  名称：

  Syntheses and coordination chemistry of methylpyridylphosphine oxide ligands with copper(II)

  摘要：

  The coordination properties of three heterofunctional phosphine oxide ligands, 2-methylpyridyldiphenylphosphine oxide (L1), phenylphosphino-bis-2-methylpyridine oxide (L2) and phenylphosphino-bis-2-methylpyridine N,N',P-trioxide (L3) with Cu(II) is described. The X-ray crystal structures of the compounds display a distorted octahedral geometry, which exhibit Jahn-Teller distortions. In compounds 1 and 2, the L1 and 12 ligands react with Cu(BF4)(2) in a 2:1 ligand to metal ratio, respectively, with the BF4 anions interacting with the metal center. L3 reacts with Cu(BF4)(2) in 1:1 and 2:1 ligand/metal ratios to form compounds 3 and 4, respectively. Addition of either 2,2'-bipyridine or 4,4'-bipyridine to reaction solutions containing Cu(BF4)(2) and U produces a discrete molecule (5) and a polymeric structure (7), respectively. The reaction of both bipyridines in the presence of Cu(BF4)(2) and L3 gives rise to a discrete molecule (6) characterized by two octahedral coppers interconnected by the 4,4'-bipyridine. The electrochemical and photophysical properties of all compounds were investigated by cyclic voltammetry (CV) and UV-Vis, as they exhibited no emission or excitation in fluorimetric experiments. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2010.02.019

文献信息

• Catalytic Deoxygenative Coupling of Aromatic Esters with Organophosphorus Compounds
  作者：Miki B. Kurosawa、Ryota Isshiki、Kei Muto、Junichiro Yamaguchi

  DOI：10.1021/jacs.0c02839

  日期：2020.4.22

  We have developed a deoxygenative coupling of aromatic esters with diarylphosphine oxides/dialkyl phosphonates under palladium ca-talysis. In this reaction, aromatic esters can work as novel benzylation reagents to give the corresponding benzylic phosphorus compounds. The key of this reaction is the use of phenyl esters, an electron-rich diphosphine as a ligand, and sodium formate as a hydrogen source

  我们开发了在钯催化下芳族酯与二芳基膦氧化物/二烷基膦酸酯的脱氧偶联。在该反应中，芳族酯可作为新型苄基化试剂生成相应的苄基磷化合物。该反应的关键是使用苯酯、富电子二膦作为配体，以及甲酸钠作为氢源。芳基羧酸也适用于该反应，使用 (Boc)2O 作为添加剂。钯/dcype 用于激活酯的酰基 CO 键并支持甲酸钠的还原。
• Synthesis and Properties of New (Phosphinoylmethyl)Pyridine N-Oxides
  作者：Sylvie L. Pailloux、Daniel Rosario-Amorin、Manab Chakravarty、Jean-Michel Camus、Karen Ann Smith、Eileen N. Duesler、Diane A. Dickie、Robert T. Paine、Kevin K. Klausmeyer、Daniel A. Padron、Benjamin P. Hay、Laetitia H. Delmau

  DOI：10.1002/zaac.201300099

  日期：2013.6

  -oxy-pyridin-2yl)methyl]pyridine N-oxides (5a, b) and the 2-[1-(diarylphosphinoyl)-1, 1-bis(1-oxy-methylpyridin-2-yl)methyl]pyridines (6a, b), respectively. The “short-arm“ pyridine fragment of 11a, b resists N-oxidation, and the fully oxidized molecules, 2-[1-(diarylphosphinoyl)-1, 1-bis(1-oxy-methylpyridin-2-yl)methyl]pyridine N-oxides (7a, b) were not isolated. Molecular mechanics calculations for

  2-[1-(二芳基膦酰基)-1-(吡啶-2-基)甲基]吡啶、(8a, b)和2-[1-(二芳基膦酰基)-1, 1-双(甲基吡啶-2基)的合成描述了基于 2-甲基吡啶片段取代到 2-[（二芳基）膦酰基甲基] 吡啶平台的外亚甲基碳原子上的甲基]吡啶（11a，b）（Ar = C6H5 和 2-CF3C6H4）。8a、b 和 11a、b 的 N-氧化产生 2-[1-(二芳基膦酰基)-1-(1-oxy-pyridin-2yl)methyl] 吡啶 N-氧化物 (5a, b) 和 2-[1 -(二芳基膦酰基)-1、1-双(1-氧-甲基吡啶-2-基)甲基]吡啶(6a、b)。11a、b 的“短臂”吡啶片段可抵抗 N-氧化，而完全氧化的分子 2-[1-(二芳基膦酰基)-1, 1-双(1-氧-甲基吡啶-2-基)甲基]没有分离出吡啶 N-氧化物 (7a, b)。气相 1 的分子力学计算：1 配体/镧系元素配合物表明
• Copper(II) Acetate‐Catalyzed Synthesis of Phosphorylated Pyridines <i>via</i> Denitrogenative C−P Coupling between Pyridotriazoles and P(O)H Compounds
  作者：Ruwei Shen、Chao Dong、Jianlin Yang、Li‐Biao Han

  DOI：10.1002/adsc.201800909

  日期：2018.11.5

  A new inexpensive copper‐catalyzed denitrogenative C−P coupling reaction of pyridotriazoles with P(O)H compounds has been developed. The reaction proceeds via a process of copper‐catalyzed P(O)−H insertion into the pyridyl carbene intermediates generated in situ from pyridotriazoles. This reaction provides a new and effective method for the synthesis of a variety of 2‐picolylphosphoryl compounds.

  吡啶三唑与P（O）H化合物的新型廉价铜催化脱氮C-P偶联反应已得到开发。该反应通过铜催化的P（O）-H插入由吡啶三唑原位生成的吡啶基卡宾中间体的过程进行。该反应为合成各种2-picolylphosphoryl化合物提供了一种新的有效方法。
• Synthesis, Lanthanide Coordination Chemistry, and Liquid–Liquid Extraction Performance of CMPO-Decorated Pyridine and Pyridine <i>N</i>-Oxide Platforms
  作者：Daniel Rosario-Amorin、Sabrina Ouizem、Diane A. Dickie、Yufeng Wen、Robert T. Paine、Jian Gao、John K. Grey、Ana de Bettencourt-Dias、Benjamin P. Hay、Lætitia H. Delmau

  DOI：10.1021/ic3025342

  日期：2013.3.18

  tetradentate chelate structures are obtained for several 1:1 complexes of 9 while a pentadentate chelate structure is observed with 10. Emission spectroscopy for one complex, [Eu(9)(NO3)3], in methanol, shows that the Eu(III) ion resides in a low-symmetry site. Lifetime measurements for methanol and deuterated methanol solutions indicate the presence of four methanol molecules in the inner coordination sphere

  描述了一组新的配体的合成，所述新的配体包含一个或两个连接在吡啶和吡啶N-氧化物平台上的氨基甲酰基甲基膦氧化物（CMPO）片段。分子力学分析为吡啶气相镧系元素-配体相互作用Ñ -oxides指示该三官能NOPOCO分子，2 - [PH 2 P（O）] [C（O）净2 ] C（H）}℃ 5 ħ 4 NO（7）和2-[Ph 2 P（O）] [C（O）NEt 2 ] CHCH 2 } C 5 H 4 NO（8）和五官能NOPOP'O'COC'O'分子，2 ，6-[Ph 2 P（O）] [C（O）NEt2 ] C（H）} 2 C 5 H 3 NO（9）和2,6-[Ph 2 P（O）] [C（O）NEt 2 ] CHCH 2 } 2 C 5 H 3 NO（10）应当能够以最小的应变分别采用三齿和五齿螯合物结构。作为对这些预测的检验，对N-氧化物衍生物的选定镧系配位化学进行了研究。晶体结构分析揭示了含有7而8的1：1
• Palladium(II) and platinum(II) derivatives with N,O ligands
  作者：Giovanni Minghetti、Sergio Stoccoro、Maria Agostina Cinellu、Antonio Zucca、Mario Manassero、Mirella Sansoni

  DOI：10.1039/a805842c

  日期：——

  The preparation of a series of Pd(II) and Pt(II) derivatives with three N,O hybrid ligands 1-(2-pyridyl)ethyldiphenylphosphine oxide, L1; (2-pyridyl)methyldiphenylphosphine oxide, L2 and 2-pyridyldiphenylphosphine oxide, L3 is described. Depending on the ligand to metal molar ratio, either 1∶1 [LMCl2] [L1PdCl2] 1, [L2PdCl2] 2, [L3PdCl2] 3, [L1PtCl2] 4} or 2∶1 [L2MCl2] [L12PdCl2] 5, [L22PdCl2] 6, [L12PtCl2]

  具有三个N，O杂配体1-（2-吡啶基）乙基二苯膦氧化物L 1的一系列Pd（II）和Pt（II）衍生物的制备；描述了（2-吡啶基）甲基二苯基膦氧化物L 2和2-吡啶基二苯基膦氧化物L 3。取决于配体与金属的摩尔比，1∶1 [LMCl 2 ] [L 1 PdCl 2 ] 1，[L 2 PdCl 2 ] 2，[L 3 PdCl 2 ] 3，[L 1 PtCl 2 ] 4}或21：1 [L 2 MCl 2 ] [L 1 2 PdCl得到[ 2 ] 5，[L 2 2 PdCl 2 ] 6，[L 1 2 PtCl 2 ] 7}加合物。另外，通过用AgPF 6处理络合物5，已经分离出一种离子物质[L 1 2 Pd] [PF 6 ] 2 8。通过X射线衍射解析了化合物5b·MeOH·H 2 O，6·MeOH和4·CH 2 Cl 2的固态结构。的结构的反式- [L 1 2的PdCl 2 ] 5B（5非对映体中的一个）和反式-