1-(4-Chlorophenyl)-2-[2-diphenylphosphanylethyl(diphenyl)-lambda5-phosphanylidene]ethanone | 1258232-06-2

• 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: 1-(4-Chlorophenyl)-2-[2-diphenylphosphanylethyl(diphenyl)-lambda5-phosphanylidene]ethanone
• 英文别名: 1-(4-chlorophenyl)-2-[2-diphenylphosphanylethyl(diphenyl)-λ5-phosphanylidene]ethanone
• CAS: 1258232-06-2
• 化学式: C₃₄H₂₉ClOP₂
• 分子量: 551.004
• InChiKey: MQNGYZRRIKJPJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  dichloro(cycloocta-1,5-diene)palladium (II) 、 1-(4-Chlorophenyl)-2-[2-diphenylphosphanylethyl(diphenyl)-lambda5-phosphanylidene]ethanone 以 二氯甲烷 为溶剂， 以79%的产率得到
  参考文献：
  名称：

  Synthesis, characterization and structural studies of new palladium(II) complexes including non-symmetric phosphorus ylides

  摘要：

  The reaction of the non-symmetric phosphorus ylides, Ph2P(CH2)(n)PPh2C(H)C(O)PhR [Y-1-Y-4: n = 1, R = Cl, Br, NO2, OCH3 and Y-5-Y-8: n = 2, R = Cl, Br, NO, OCH3] with dichloro(1,5-cyclooctadiene)palladium( II) in dichloromethane under mild conditions afford the monomeric P-C chelated complexes, [(Y)PdCl2] (Y = Y-1-Y-8). These complexes were fully characterized by elemental analysis and spectroscopic techniques such as IR, H-1, P-31, and C-13 NMR. In addition, the identity of complexes [(Y-5)PdCl2] (1b) and [(Y-8)PdCl2] (4b) was unequivocally determined by single crystal X-diffraction techniques, both structures consisting of six-membered rings formed by coordination of the ligands through the phosphine group and the ylidic carbon atom to the metal center. The coordination geometry around the Pd atoms in both these complexes be defined as slightly distorted square planar. Furthermore, their electrochemical behavior was also investigated by cyclic voltammeters, thus the cyclic voltammetry of complex [(Y-1)PdCl2], in dichloromethane solution with Pt electrode, shows that the redox reaction of the pair Pd(II)/Pd(0) is irreversible with the cathodic peak potential at -1.08 V versus Ag wire. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2010.07.072
• 作为产物：
  描述：

  2'-溴-4-氯苯乙酮 、 1,2-双(二苯基膦)乙烷 在 三乙胺 作用下， 以 丙酮 为溶剂， 以76%的产率得到1-(4-Chlorophenyl)-2-[2-diphenylphosphanylethyl(diphenyl)-lambda5-phosphanylidene]ethanone
  参考文献：
  名称：

  Synthesis, characterization and structural studies of new palladium(II) complexes including non-symmetric phosphorus ylides

  摘要：

  The reaction of the non-symmetric phosphorus ylides, Ph2P(CH2)(n)PPh2C(H)C(O)PhR [Y-1-Y-4: n = 1, R = Cl, Br, NO2, OCH3 and Y-5-Y-8: n = 2, R = Cl, Br, NO, OCH3] with dichloro(1,5-cyclooctadiene)palladium( II) in dichloromethane under mild conditions afford the monomeric P-C chelated complexes, [(Y)PdCl2] (Y = Y-1-Y-8). These complexes were fully characterized by elemental analysis and spectroscopic techniques such as IR, H-1, P-31, and C-13 NMR. In addition, the identity of complexes [(Y-5)PdCl2] (1b) and [(Y-8)PdCl2] (4b) was unequivocally determined by single crystal X-diffraction techniques, both structures consisting of six-membered rings formed by coordination of the ligands through the phosphine group and the ylidic carbon atom to the metal center. The coordination geometry around the Pd atoms in both these complexes be defined as slightly distorted square planar. Furthermore, their electrochemical behavior was also investigated by cyclic voltammeters, thus the cyclic voltammetry of complex [(Y-1)PdCl2], in dichloromethane solution with Pt electrode, shows that the redox reaction of the pair Pd(II)/Pd(0) is irreversible with the cathodic peak potential at -1.08 V versus Ag wire. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2010.07.072

文献信息

• Monodentate palladium(0)–[60]fullerene complexes of diphosphine ligands as efficient and sustainable nanocatalysts for the Mizoroki–Heck coupling reaction of aryl chlorides
  作者：Seyyed Javad Sabounchei、Marjan Hosseinzadeh、Morteza Zarepour-jevinani、Bahram Ghanbari

  DOI：10.1039/c7nj00741h

  日期：——

  are the most desirable substrates from an industrial point of view in Csp2–Csp2 coupling reactions. Furthermore, overall bonding modes in the palladafullerenes of bifunctional diphosphine-based ligands were investigated by spectroscopic analysis and theoretical calculations. DFT studies of geometry-optimized monodentate and bidentate structures for 1 were calculated at the B3LYP/LANL2MB level of theory

  富勒烯的两个单核配位络合物[60]用Pd（DBA）2（DBA =苄基丙酮），[（η 2 -C 60）的Pd（PH 2 P（CH 2）2 PPH 2 C（H）C（O）R ）2 ]（R = C 10 H 7（1），C 6 H 4 Cl（2）），已使用简单的方法制备，以探索钯催化和纳米碳化学的新方向。钯（0）– [60]富勒烯配合物不对称磷磷化物的特征在于1 H，13 C和31P NMR光谱方法和其他常规技术，例如IR，TGA，SEM，ICP-OES，EDX和TEM分析。归因于具有膦官能化富勒烯的Pd纳米颗粒的分散性增强和尺寸均匀，所制备的催化剂显示出与芳基氯的Mizoroki-Heck偶联反应相当的催化活性。由于其丰度高且成本低，从工业角度来看，在Csp 2 –Csp 2偶联反应中，芳基氯化物是最理想的底物。此外，通过光谱分析和理论计算研究了基于双官能团基于二膦的配体的全富勒烯中的整体键合模式
• Synthesis, Spectroscopic and Antibacterial Studies of Silver(I) Complexes with Bidentate Phosphorus Ylides
  作者：Seyyed Javad Sabounchei、Mahbubeh Pourshahbaz、Roya Karamian、Mostafa Asadbegy

  DOI：10.3184/174751914x13928114519908

  日期：2014.3

  P-coordinated complexes of the type [AgNO₃Ph₂P(CH₂)_nPPh₂C(H)C(O)C₆H₄R}]₂ ( n = 1 or 2; R=Cl, Br, NO₂ or OCH₃), have been synthesised by reactions of AgNO₃ with the appropriate phosphorus ylides. The antibacterial effects of DMSO-solutions of all compounds have been evaluated by the agar disc diffusion method against six Gram positive and Gram negative bacteria.

  通过 AgNO3 与适当的磷酰化物反应，合成了[AgNO3Ph2P(CH2)nPPh2C(H)C(O)C6H4R}]2（n = 1 或 2；R=Cl、Br、NO2 或 OCH3）类型的 P 配位复合物。通过琼脂盘扩散法评估了所有化合物的 DMSO 溶液对六种革兰氏阳性和革兰氏阴性细菌的抗菌效果。
• Synthesis and characterization of mononuclear oxime-based palladacycles incorporating phosphorus ylides: application as a catalyst in Suzuki cross coupling reactions and their biological activities
  作者：Ahmadreza Shiralinia、Sepideh Samiee、Elham Hoveizi

  DOI：10.1080/00958972.2021.1993206

  日期：2021.8.3

  bidentate phosphorus ylides (1-4). These palladacycles were applied for Suzuki-Miyaura cross-coupling reactions under aerobic conditions in EtOH/H2O solvent. Upon optimizing the reaction conditions, complex 3 was highly efficient to catalyze the cross-coupling of aryl halides with phenylboronic acids at a 0.44 mol % palladium loading. Also, the cytotoxic effects of 1-4 were evaluated by an MTT assay in three

  摘要 [Pd C,N -C 6 H 4 C(Me)=NOH}-2}(Ph 2 PCH 2 CH 2 PPh 2 C(H)C(O) C 6 H 4 X)]ClO 4 (X = Cl ( 1 ), Br ( 2 ), NO 2 ( 3 ), OCH 3 ( 4 )) 由 [Pd C,N -C 6 H 4 C(Me)=NOH}-2}( μ- Cl)] 2与磷叶立德在二氯甲烷中回流。所得化合物通过FT-IR、NMR（1 H、13 CH} 和31 PH}）光谱方法和元素分析表征。氯化物桥的裂解形成的四个新的单核基于肟的钯环结合的双齿磷叶立德（1 - 4）。这些钯环在 EtOH/H 2 O 溶剂中的有氧条件下用于 Suzuki-Miyaura 交叉偶联反应。在优化反应条件后，配合物3在 0.44 mol% 钯负载下高效催化芳基卤化物与苯基硼酸的交叉偶联。此外，细胞毒作用1 - 4 HT29
• New chlorine bridged binuclear silver(I) complexes of bidentate phosphorus ylides: Synthesis, spectroscopy, theoretical and anti-bacterial studies
  作者：Seyyed Javad Sabounchei、Mahbubeh Pourshahbaz、Sadegh Salehzadeh、Mehdi Bayat、Roya Karamian、Mostafa Asadbegy、Hamid Reza Khavasi

  DOI：10.1016/j.poly.2014.09.030

  日期：2015.1

  Silver(I) halides react with bidentate phosphorus ylides of the type Ph2P(CH2)(n)PPh2=(H)C(O)C6H4R (n = 1,2) (R = 4-Cl (Y-1, Y-5), 4-Br (Y-2, Y-6), 4-NO2 (Y-3, Y-7), 4-OMe (Y-4, Y-8)) in CH3CN as a solvent in equimolar ratios to give complexes of the formulae [(Ph2P(CH2)(n)PPh2C(H)C(O)C6H4R)AgX](2) (X = Cl (1, 4, 7, 10, 13, 16, 19, 22), Br (2, 5, 8, 11, 14, 17, 20, 23) and 1(3, 6, 9, 12, 15, 18, 21, 24)). X-ray analysis demonstrate a binuclear chloro-bridged structure (Y-Ag(mu-Cl)(2)Ag-Y) in which the ligand coordinates to the silver center through the P atom in complexes 1 and 10. However, both the theoretical and experimental data indicate that the ylidic carbon also has a weak interaction with the Ag ion. Characterization of the obtained compounds was performed by elemental analysis, IR, H-1, P-31 and C-13 NMR spectroscopy. In addition, the DMSO dissolved ligands and their complexes were screened in vitro for their antibacterial activity against 6 Gram positive and negative bacteria. All the synthesized compounds exhibited significant activity, especially against Gram negative bacteria. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis, characterization and structural studies of new palladium(II) complexes including non-symmetric phosphorus ylides
  作者：Seyyed Javad Sabounchei、Sepideh Samiee、Davood Nematollahi、Ali Naghipour、David Morales-Morales

  DOI：10.1016/j.ica.2010.07.072

  日期：2010.11

  The reaction of the non-symmetric phosphorus ylides, Ph2P(CH2)(n)PPh2C(H)C(O)PhR [Y-1-Y-4: n = 1, R = Cl, Br, NO2, OCH3 and Y-5-Y-8: n = 2, R = Cl, Br, NO, OCH3] with dichloro(1,5-cyclooctadiene)palladium( II) in dichloromethane under mild conditions afford the monomeric P-C chelated complexes, [(Y)PdCl2] (Y = Y-1-Y-8). These complexes were fully characterized by elemental analysis and spectroscopic techniques such as IR, H-1, P-31, and C-13 NMR. In addition, the identity of complexes [(Y-5)PdCl2] (1b) and [(Y-8)PdCl2] (4b) was unequivocally determined by single crystal X-diffraction techniques, both structures consisting of six-membered rings formed by coordination of the ligands through the phosphine group and the ylidic carbon atom to the metal center. The coordination geometry around the Pd atoms in both these complexes be defined as slightly distorted square planar. Furthermore, their electrochemical behavior was also investigated by cyclic voltammeters, thus the cyclic voltammetry of complex [(Y-1)PdCl2], in dichloromethane solution with Pt electrode, shows that the redox reaction of the pair Pd(II)/Pd(0) is irreversible with the cathodic peak potential at -1.08 V versus Ag wire. (C) 2010 Elsevier B.V. All rights reserved.