N-(2-pyridinyl)-P,P-diphenylphosphinic acid amide | 41049-57-4

• 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: N-(2-pyridinyl)-P,P-diphenylphosphinic acid amide
• 英文别名: N-(2-pyridinyl)-P,P-diphenyl-phosphonic amide；P,P-diphenyl-N-(2-pyridinyl) phosphinic amide；P,P-diphenyl-N-(pyridin-2-yl)phosphinic amide；N-(2-pyridinyl)amino-diphenylphosphine oxide；N-(2-pyridinyl)aminodiphenylphosphine oxide；N-(2-pyridinyl)diphenylphosphinic amide；N-diphenylphosphorylpyridin-2-amine
• CAS: 41049-57-4
• 化学式: C₁₇H₁₅N₂OP
• 分子量: 294.293
• InChiKey: HGVNNBNMBVMCDZ-UHFFFAOYSA-N

物化性质

• 熔点：
  177-180 °C
• 沸点：
  457.1±37.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cobalt(II) nitrate hexahydrate 、 N-(2-pyridinyl)-P,P-diphenylphosphinic acid amide 以 甲醇 为溶剂， 以73%的产率得到cis-[Co(N-(2-pyridinyl)-P,P-diphenyl-phosphonic amide)2(NO3)][NO3]
  参考文献：
  名称：

  Syntheses, structures and ligand conformations of Cu(II), Co(II) and Ag(I) complexes containing the phosphinic amide ligands

  摘要：

  The syntheses, structures and ligand conformations of the complexes trans-Cu(L1)(2)(ClO4)(2), (L1 = N-(2-pyrimidinyl)-P,P-diphenyl-phosphinic amide), 1, [trans-Co(L1)(2)(CH3OH)(2)](ClO4)2 center dot O(C2H5)(2), 2, [trans-Co(L2)(2)(H2O)(2)](ClO4)(2)center dot 2CH(3)OH, (L2 = N-(2-pyridinyl)-P,P-diphenyl-phosphinic amide), 3,]cis-Co(L2)(2) (NO3)](NO3), 4, and [Ag(L3)(NO3)(CH3CN)](infinity), (L3 = N-(6-methyl-2-pyridinyl)-P,P-diphenyl-phosphinic amide), 5, are reported. The L1 and 12 ligands in the monomeric complexes 1-4 chelate the metal centers through the pyrimidyl/pyridyl nitrogen atoms and the phosphinic amide oxygen atoms, whereas the L3 ligands in complex 5 bridge the metal centers, forming a 1-D zigzag chain. The chelating L2 ligands in complexes 3 and 4 adopt cis conformations and the bridging L3 ligand in complex 5 adopts a trans conformation, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2011.10.022
• 作为产物：
  描述：

  2-((diphenylphosphino)amido)pyridine 在 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以81%的产率得到N-(2-pyridinyl)-P,P-diphenylphosphinic acid amide
  参考文献：
  名称：

  The co-ordination chemistry of 2-(diphenylphosphinoamino)pyridine †

  摘要：

  2-(二苯膦氨基)吡啶，dppap [Ph2PNHpy]，以及超过40个示例性的其配合物已被制备。在一系列钯、铂和金配合物中，示例了中性（以及双齿去质子化配体）的单齿、双齿和桥联配位方式。十个示范性例子通过单晶X射线衍射进行了表征。Ph2PNHpy以氢键结合的二聚体对形式存在；cis-[PtCl(Ph2PNHpy-P,N){Ph2PNHpy-P}]Cl通过氢键形成无限链；cis-[Pt(Ph2PNpy-P,N)2]和cis-[Pd(Ph2PNpy-P,N)2]是同构的。cis-[Pd(Ph2PNHpy-P,N)2][BF4]2、[AuCl(Ph2PNHpy-P)]、[Pt(C8H12OMe)(Ph2PNpy-P,N)]·H2O展示了氢键结合，cis-[PtCl(Ph2PNHpy-P,N)(PMe3)]Cl、cis-[PtCl(Ph2PNpy-P,N)(PMe3)]和cis-[PtCl(Ph2PNHpy-P,N)(P(OPh)3)]Cl的结构也被报道。

  DOI：

  10.1039/b003294h

文献信息

• The co-ordination chemistry of 2-(diphenylphosphinoamino)pyridine †
  作者：Stephen M. Aucott、Alexandra M. Z. Slawin、J. Derek Woollins

  DOI：10.1039/b003294h

  日期：——

  2-(Diphenylphosphinoamino)pyridine, dppap [Ph2PNHpy], and over 40 illustrative examples of its complexes have been prepared. Monodentate, bidentate and bridging co-ordination of the neutral (and bidentate deprotonated ligand) has been demonstrated in a range of palladium, platinum and gold complexes. Ten demonstrative examples have been characterised by single crystal X-ray diffraction. Ph2PNHpy exists as hydrogen-bonded dimer pairs; cis-[PtCl(Ph2PNHpy-P,N)Ph2PNHpy-P}]Cl packs in hydrogen-bonded infinite chains; cis-[Pt(Ph2PNpy-P,N)2] and cis-[Pd(Ph2PNpy-P,N)2] are isomorphous. The structures of cis-[Pd(Ph2PNHpy-P,N)2][BF4]2, [AuCl(Ph2PNHpy-P)], [Pt(C8H12OMe)(Ph2PNpy-P,N)]·H2O illustrating hydrogen-bonding, cis-[PtCl(Ph2PNHpy-P,N)(PMe3)]Cl, cis-[PtCl(Ph2PNpy-P,N)(PMe3)] and cis-[PtCl(Ph2PNHpy-P,N)(P(OPh)3)]Cl are also reported.

  2-(二苯膦氨基)吡啶，dppap [Ph2PNHpy]，以及超过40个示例性的其配合物已被制备。在一系列钯、铂和金配合物中，示例了中性（以及双齿去质子化配体）的单齿、双齿和桥联配位方式。十个示范性例子通过单晶X射线衍射进行了表征。Ph2PNHpy以氢键结合的二聚体对形式存在；cis-[PtCl(Ph2PNHpy-P,N)Ph2PNHpy-P}]Cl通过氢键形成无限链；cis-[Pt(Ph2PNpy-P,N)2]和cis-[Pd(Ph2PNpy-P,N)2]是同构的。cis-[Pd(Ph2PNHpy-P,N)2][BF4]2、[AuCl(Ph2PNHpy-P)]、[Pt(C8H12OMe)(Ph2PNpy-P,N)]·H2O展示了氢键结合，cis-[PtCl(Ph2PNHpy-P,N)(PMe3)]Cl、cis-[PtCl(Ph2PNpy-P,N)(PMe3)]和cis-[PtCl(Ph2PNHpy-P,N)(P(OPh)3)]Cl的结构也被报道。
• Practical Synthesis of Phosphinic Amides/Phosphoramidates through Catalytic Oxidative Coupling of Amines and P(O)−H Compounds
  作者：Chen Tan、Xinyuan Liu、Huanxin Jia、Xiaowen Zhao、Jian Chen、Zhiyong Wang、Jiajing Tan

  DOI：10.1002/chem.201904237

  日期：2020.1.16

  Herein, we report a highly efficient ZnI2 -triggered oxidative cross-coupling reaction of P(O)-H compounds and amines. This operationally simple protocol provides unprecedented generic access to phosphinic amides/phosphoramidate derivatives in good yields and short reaction time. Besides, the reaction proceeds under mild conditions, which avoids the use of hazardous reagents, and is applicable to scale-up

  在本文中，我们报告了P​​（O）-H化合物与胺类的高效ZnI2触发的氧化交叉偶联反应。该操作简单的方案以高收率和较短的反应时间提供了对次膦酰胺/氨基磷酸酯衍生物的空前通用访问。此外，该反应在温和的条件下进行，避免了使用有害试剂，并且适用于按比例放大的合成以及药物分子的后期功能化。立体特异性偶联也可以从容易获得的光学富集的P（O）-H化合物中获得。
• The Chan-Evans-Lam N -arylation of phosphonic/phosphinic amides
  作者：Yuqin Xu、Qiong Su、Wanrong Dong、Zhihong Peng、Delie An

  DOI：10.1016/j.tet.2017.06.028

  日期：2017.8

  A stoichiometric copper(II)-mediated arylation protocol of phosphinamides and phosphonamides was herein demonstrated. Various unreported N-aryl phosphinamides and phosphonamides were successfully prepared through Chan-Evans-Lam reaction with high efficiency (up to 88% yields) and good functional groups tolerance (30 examples) in the absence of any ligands or co-catalysts.

  本文证明了化学计量的铜（II）介导的次膦酰胺和膦酰胺的芳基化方案。在没有任何配体或助催化剂的情况下，通过Chan-Evans-Lam反应以高效率（高达88％的收率）和良好的官能团耐受性（30个实例）成功地制备了各种未报告的N-芳基次膦酰胺和膦酰胺。
• Steric and electronic control over the structural diversity of N-(n-pyridinyl) diphenylphosphinic amides (n = 2 and 4) as difunctional ligands in triphenyltin(<scp>iv</scp>) adducts
  作者：K. Gholivand、A. Gholami、S. K. Tizhoush、K. J. Schenk、F. Fadaei、A. Bahrami

  DOI：10.1039/c4ra06212d

  日期：——

  bipyramidal geometry surrounding the tin(IV). Both of the ligands function in an ambidentate mode, ligating through either the O or N atom. The experimental and theoretical (DFT) studies show that the Sn(IV) interacts more strongly with the N-pyridine atom than the PO functional group. Furthermore, DFT calculations, at the B3LYP level, have been carried out to determine the deeper reasons for the adopted

  合成了两个双官能团配体的三苯基锡（IV）加合物，N-（n-吡啶基）二苯基次膦酰胺（n = 2和4），并通过1 H，31 P，119 Sn NMR和IR进行了表征。将配合物的光谱性质与相应配体的光谱性质进行比较。配合物的晶体结构通过X射线晶体学测定，其揭示了锡（IV）周围的三角双锥体几何形状。两个配体均以双键模式起作用，通过O或N原子连接。实验和理论（DFT）研究表明，Sn（IV）与N-吡啶原子的相互作用比P O官能团的相互作用更强。此外，已经在B3LYP级别上进行了DFT计算，以确定在复合物中采用键合模式的更深层原因。阐明了配体结构对配位行为的影响以及氢键对所得配合物稳定性的影响。结果表明，分子间氢键在有机锡（IV）化合物的分子结构和超分子缔合中具有重要作用。
• Synthesis, characterization, biological properties, and molecular docking studies of new phosphoramide-based Ag(<scp>i</scp>) complexes
  作者：Khodayar Gholivand、Mohammad Faraghi、Samaneh K. Tizhoush、Sara Ahmadi、Mostafa Yousefian、Fahimeh Mohammadpanah、S. Mark Roe

  DOI：10.1039/d2nj02748h

  日期：——

  Two new Ag(I) complexes of N-(n-pyridinyl)diphenylphosphinic amide (n = 2 and 3) (Lo and Lm) with formulae Ag(Lo)NO3 (Co) and Ag(Lm)NO3·H2O (Cm) were synthesized. Infrared, NMR, and elemental analyses were applied to fully characterize them. The crystal structure of Cm was also assessed using single-crystal X-ray diffraction and the monoclinic nature of the silver complex was illustrated. The organization

  N -( n -吡啶基)二苯基次膦酰胺 ( n = 2 和 3) ( L o和L m ) 的两个新 Ag( I ) 配合物，分子式为 Ag( L o )NO 3 ( C o ) 和 Ag( L m )合成了NO 3 ·H 2 O ( C m )。应用红外、核磁共振和元素分析来充分表征它们。C m的晶体结构还使用单晶 X 射线衍射进行了评估，并说明了银络合物的单斜晶系性质。还研究了四个协调的双核 Ag( I ) 配合物的组织和分子间的相互作用。超分子是由各种分子间相互作用、氢键、M⋯π、π⋯π 接触和CH⋯π 合成子协同作用形成的。采用 MIC、MBC 和 DDA 方法对 Ag( I ) 复合物和相应的配体对革兰氏阴性菌（大肠杆菌）和革兰氏阳性菌（金黄色葡萄球菌）进行了抗菌研究，C m显示出比C o更高的杀菌活性。对抗两种细菌（大肠杆菌；MIC = 9.7 μg mL -1和金黄色葡萄球菌；MIC