N-(diphenylphosphino)benzamide | 234430-12-7

• 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: N-(diphenylphosphino)benzamide
• 英文别名: Phenylphosphonsaeure-phenylester-benzamid；N-diphenylphosphanylbenzamide
• CAS: 234430-12-7
• 化学式: C₁₉H₁₆NOP
• 分子量: 305.316
• InChiKey: XVOJLFHTOYWWPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 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：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(diphenylphosphino)benzamide 在 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 N-(diphenylphosphoryl)benzamide
  参考文献：
  名称：

  Spectroscopic and structural characterization of O,O′-(diphenylphosphineoxide)amidate and acetylacetonate complexes of pentacoordinate nickel(II)

  摘要：

  Heteroleptic nickel pentacoordinate complexes with the macrocyclic ligands 2,4,4-trimethyl-1,5,9-triazacyclododec-1-ene (Me-3-mcN(3)) or its 9-methyl derivative (Me-4-mcN(3)), as ancillary ligands, and O,O'-(diphenylphosphineoxide) amidate ligands, [RC(O)NP(O)Ph-2] (R = C6H6 (1), C5H4N (2), C4H3S (3)), have been prepared as well as related acetylacetonate derivatives. The complexes have been studied by spectroscopic methods (IR, UV-Vis and H-1 NMR). In acetone solution, the complexes exhibit isotropically shifted H-1 NMR resonances. The full assignment of these resonances has been achieved using one- and two-dimensional H-1 NMR techniques. The single-crystal structures of {(Me-4-mcN(3)) Ni[OP(Ph-2)NC(Tf)O]}[PF6] (9) and {(Me-3-mcN(3))Ni(acac)}[PF6] (10) have been established by X-ray diffraction. (C) 2008 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2008.09.075
• 作为产物：
  描述：

  苯甲酰胺 、 二苯基氯化膦 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以66 %的产率得到N-(diphenylphosphino)benzamide
  参考文献：
  名称：

  用于乙烯/丙烯酸酯共聚的膦-亚氨酸盐负载镍催化剂

  摘要：

  合成了膦-亚氨酸盐负载的镍催化剂并测试了乙烯/丙烯酸酯共聚活性。 (pyridine) 2 Ni(CH 2 Si(CH 3 ) 3 ) 2 (py 2 Ni(CH 2 TMS) 2 ) 的膦-酰胺金属化研究表明，金属化通过中间膦-酰胺络合物 ([P,O –酰胺]Ni(CH 2 TMS) 2 )。随后酰胺 N-H 的去质子化可得到膦-亚氨酸盐负载的镍络合物 ([P,O-imidate]pyNi(CH 2 TMS))。配体的亚氨酸酯形式被证明对于聚合活性至关重要。本文所述的膦-亚氨酸镍催化剂能够生产分子量( M w )为700至120,000 g/mol且在某些情况下丙烯酸酯掺入量>2.6 mol%的乙烯/丙烯酸酯共聚物。确定膦芳基上的半不稳定烷氧基对于实现高M w和丙烯酸酯的掺入是必要的。这些结果表明，膦酰胺是一种经过充分研究的配体类，可以以亚胺酸酯形式使用以获得高活性的中性镍聚合催化剂。

  DOI：

  10.1021/acs.organomet.4c00034

文献信息

• The First Six-Membered “True” Heterocycle - Hydrogen-Bond-Assisted Ladder Formation in a KOCNPS Ring System
  作者：Tuan Q. Ly、Alexandra M. Z. Slawin、J. Derek Woollins

  DOI：10.1002/(sici)1521-3773(19981002)37:18<2501::aid-anie2501>3.0.co;2-2

  日期：1998.10.2

  A ladder of alternating K2 S2 and K2 O2 rings exists in K[Ph2 P(S)NC(O)Ph]⋅MeOH, the first six-membered "true" heterocycle, in the solid state (see picture). A simple P-N bond-forming reaction between benzamide and Ph2 PCl gives the precursor Ph2 P(S)NHC(O)Ph, from which the potassium salt can be generated by reaction with KOtBu.

  固态的第一个六元“真正”杂环K [Ph 2 P（S）NC（O）Ph]⋅MeOH中存在一个交替排列的K 2 S 2和K 2 O 2环的阶梯（参见图片） ）。苯甲酰胺和Ph 2 PCl之间的简单PN键形成反应得到前体Ph 2 P（S）NHC（O）Ph，可以通过与KOtBu反应生成钾盐。
• The First Six Membered Genuine Heterocycle: [Ph₃PCu{Ph₂P(S)-N-C(O)Ph}]
  作者：M. Necas、J. Novosad、T. Q. Ly、Z. Zák、J. D. Woollins

  DOI：10.1080/10426500108546589

  日期：2001.1.1

  The synthesis and X-Ray structure of the first six membered non-ionic genuine heterocycle is reported. The non-planar ring is formed by Cu, O, C, N, P, and S and its conformation is described as pseudo boat.

  报告了前六元非离子真正杂环的合成和 X 射线结构。非平面环由 Cu、O、C、N、P 和 S 形成，其构象被描述为假船。
• Syntheses, crystal structure, photophysical property and theoretical study of a new series of iridium complexes with N-(diphenylphosphoryl)benzamide derivatives as the ancillary ligands
  作者：Tian-Yi Li、Xiao Liang、Chen Wu、Li-Sha Xue、Qiu-Lei Xu、Song Zhang、Xuan Liu、You-Xuan Zheng、Xiu-Qiang Wang

  DOI：10.1016/j.jorganchem.2014.01.014

  日期：2014.4

  Seven iridium complexes with the general structure of (tfmppy)(2)Ir(L-1-L-7) (tfmppy = 4-trifluoromethyl phenylpyridine) were synthesized, where ancillary ligands L1-L7 are fluorine-or trifluoromethyl-substituted (-F or -CF3) N-(diphenylphosphoryl)benzamide derivatives. Single crystal X-ray diffraction study was undertaken on all complexes, which showed that each adopted the distorted octahedral coordination geometry with the conventional trans-N, cis-C arrangement in the coordination sphere. Electrochemical study confirmed the electron-withdrawing -F and -CF3 substituents on the ancillary ligands have effects on the Ir-III/IV redox couples and HOMO/LUMO energy levels. Density functional theory (DFT) calculation results showed that the HOMOs are composed of Ir 5d orbital (about 55%) and pi orbitals of the phenyl rings (about 38%) in tfmppy ligands, whilst the LUMOs are mostly localized on both the phenyl and pyridine rings of tfmppy (about 90%). All the complexes own the similar emission peaks around 520 nm with short phosphorescent decay time about 2 mu s at ambient temperature and relatively high internal quantum efficiencies from 37.5 to 61.2%. This work showed that the iridium complexes with N-(diphenylphosphoryl)benzamide derivatives as the ancillary ligands possess the potential as phosphorence dopants in the organic light-emitting diodes (OLEDs). (C) 2014 Elsevier B. V. All rights reserved.
• Intermolecular interactions in the crystal structures of chlorogold(I) complexes with N-phosphinoamide ligands
  作者：Michal Navrátil、Ivana Císařová、Petr Štěpnička

  DOI：10.1016/j.ica.2020.120138

  日期：2021.2
• New Inorganic Metallacycles and the First Six-Membered Covalent “True” Heterocycle – Oxidation of RC(E)NHPPh2 (E = O or S; R = H2N, Ph, or Py) with O, S, or Se to Give RC(E)NHP(E′)Ph2 (E′ = O, S, Se) and Their Coordination Chemistry
  作者：David J. Birdsall、Jason Green、Tuan Q. Ly、Josef Novosad、Marek Necas、Alexandra M. Z. Slawin、J. Derek Woollins、Zdirak Zak

  DOI：10.1002/(sici)1099-0682(199909)1999:9<1445::aid-ejic1445>3.0.co;2-s

  日期：1999.9