4-Bromo benzoylmethylenediphenyldiphenylphosphinomethylphosphorane | 1258232-02-8

• 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: 4-Bromo benzoylmethylenediphenyldiphenylphosphinomethylphosphorane
• 英文别名: 1-(4-bromophenyl)-2-[diphenylphosphanylmethyl(diphenyl)-λ5-phosphanylidene]ethanone
• CAS: 1258232-02-8
• 化学式: C₃₃H₂₇BrOP₂
• 分子量: 581.428
• InChiKey: QHYODPOWMZYZOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.03
• 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) 、 4-Bromo benzoylmethylenediphenyldiphenylphosphinomethylphosphorane 以 二氯甲烷 为溶剂， 以85%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：

  2,4'-二溴苯乙酮 、 双二苯基膦甲烷 在 三乙胺 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 2.25h， 生成 4-Bromo benzoylmethylenediphenyldiphenylphosphinomethylphosphorane
  参考文献：
  名称：

  含有双齿膦配体的五元环钯配合物；合成、表征和高效 Suzuki 交叉偶联反应

  摘要：

  非对称磷叶立德及其钯 (II) 配合物已被合成为潜在的催化活性化合物。1 当量非对称磷叶立德 Ph2PCH2PPh2C(H)C(O)PhBr 与 [Pd(dppe)Cl2] 反应，然后用 2 当量 AgOTf 处理得到 [(dppe)Pd(Ph2PCH2PPh2C(H)C(O) PhBr)](OSO2CF3)2，其一侧包含一个五元 P,P 螯合环，另一侧包含一个五元 P,C 螯合环。通过傅里叶变换红外光谱 (FT-IR)、紫外-可见光、多核 (1H、31P 和 19F) 核磁共振 (NMR) 和电喷雾电离质谱技术合成并研究了钯配合物。FT-IR 和 31P NMR 研究表明，磷叶立德通过叶立德的末端磷 (Pc) 和亚甲基 (CH) 与钯配位。使用环钯络合物作为有效催化剂，对各种芳基卤化物进行 Suzuki 反应。各种芳基卤化物在 DMF 中与芳基硼酸偶联，在空气中，在 0.001 mol%

  DOI：

  10.1080/00958972.2012.759216

文献信息

• Synthesis, characterization, thermal, electrochemical, and DFT studies of mononuclear cyclopalladated complexes containing bidentate phosphine ligands and their biological evaluation as antioxidant and antibacterial agents
  作者：Seyyed Javad Sabounchei、Mohsen Ahmadi、Zahra Nasri、Esmaeil Shams、Sadegh Salehzadeh、Yasin Gholiee、Roya Karamian、Mostafa Asadbegy、Sepideh Samiee

  DOI：10.1016/j.crci.2012.10.006

  日期：2013.2

  the Pd atom in these complexes is defined as slightly distorted square planar by UV-Visible and DFT studies. Thermal stability of all complexes was also shown by TG/DTG methods. Furthermore, the electrochemical behavior of the complexes was investigated by cyclic voltammetry. The results indicate that all complexes are successfully synthesized from the initial ligands. All complexes were analyzed for

  摘要 非对称磷叶立德及其 Pd(II) 配合物已被合成为潜在的抗氧化和抗菌化合物，并使用多种物理化学技术阐明了它们的结构。1 当量非对称磷叶立德、Ph2PCH2PPh2C(H)C(O)PhX（X = Br (Y1)、Cl (Y2)、NO2 (Y3)、OCH3 (Y4)）与 [Pd(dppe)Cl2 的反应] (M1)，然后用 2 当量的 AgOTf 处理产生单体螯合物，[(dppe)Pd(Ph2PCH2PPh2C(H)C(O)PhX)] (OSO2CF3)2 (X = Br (C1), Cl (C2) )、NO2 (C3)、OCH3 (C4))，其中一侧含有一个五元 P,P 螯合环，另一侧含有一个五元 P,C 螯合环。通过循环伏安法、FT-IR、UV-可见光、多核（1H、31P 和 19F）核磁共振、热分析和 ESI-质谱研究合成和研究钯离子配合物。一些配合物和配体已经通过粉末 XRD 和单晶
• Palladacycle phosphine complexes as homogeneous catalysts for the Heck cross-coupling reaction at low catalyst loading under aerobic conditions
  作者：Seyyed Javad Sabounchei、Mohsen Ahmadi

  DOI：10.1016/j.ica.2013.04.048

  日期：2013.8

  A highly efficient Heck cross-coupling reaction between various aryl halides and olefins using mononuclear palladacycle complexes of the type [(Ph2P CH2CH2PPh2)Pd(Ph2PCH2PPh2C(H)C(O)PhX)](OSO2CF3)2 (X = Br (1), No2(2)) as catalyst precursors, under aerobic conditions has been developed. High yields of corresponding C–C products, low catalyst loadings and short reaction times are important features

  使用[（Ph 2 P CH 2 CH 2 PPh 2）Pd（Ph 2 PCH 2 PPh 2 C（H）C（O）PhX ）]（OSO 2 CF 3）2（X = Br（1），No 2（2））作为好氧条件的催化剂前体，已经开发出来。这些均相反应的重要特征是相应的CC产品的高收率，催化剂用量低和反应时间短。Palladacycle 1 可以在DMF中将其还原为零价钯，同时生成二氧化二ppe。
• Synthesis and Characterisation of Hg(II) Complexes Including Bidentate Phosphorus Ylides
  作者：Seyyed Javad Sabounchei、Sepideh Samiee、Mahbubeh Pourshahbaz、Sadegh Salehzadeh、Mehdi Bayat、Davood Nematollahi、Roya Karamian、Mostafa Asadbegy

  DOI：10.3184/174751914x13863254117794

  日期：2014.1

  The reaction of asymmetrical phosphorus ylides [Ph₂PCH₂PPh₂=C(H)C(O)C₆H₄R] (R=Br, OCH₃) with mercury(II) halides yielded the P, C-chelated complexes. Characterisation of these products was carried out by elemental analysis, IR, ¹H, ³¹P, and ¹³C NMR. Computational studies at DFT (BP86) level of theory are also reported. The electrochemical behaviour of complexes was also investigated by cyclic voltammetry. The synthesised compounds were screened for their antibacterial activities against six Gram negative and positive bacteria.

  不对称磷酰[Ph2PCH2PPh2=C(H)C(O)C6H4R]（R=Br，OCH3）与卤化汞（II）反应生成了 P、C-螯合络合物。通过元素分析、红外光谱、1H、31P 和 13C NMR 对这些产物进行了表征。此外，还报告了在 DFT (BP86) 理论水平上进行的计算研究。还通过循环伏安法研究了配合物的电化学行为。对合成的化合物进行了筛选，以检测它们对六种革兰氏阴性和阳性细菌的抗菌活性。
• 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。
• New dimeric phosphine ylide copper (I) complexes: Synthesis, coordination behavior, and application in Suzuki cross-coupling reactions
  作者：Seyyed Javad Sabounchei、Mahbubeh Pourshahbaz、Mohsen Ahmadi、Ali Hashemi、Hamid Reza Khavasi

  DOI：10.1016/j.inoche.2013.08.010

  日期：2013.10

  these compounds were carried out by FT-IR and multinuclear NMR technique. Elemental analysis indicate a 1:1 stoichiometry between the ylides and the Cu(I) chloride in the four complexes. The precursor complexes 1 and 3 are found to exhibit high catalytic activity in the Cu-catalyzed Suzuki cross-coupling reactions in an air atmosphere at medium catalyst loading in DMF as a solvent. The use of 5 mol%

  摘要 使用无水甲醇作为溶剂，非对称磷叶立德 Ph2P(CH2)nPPh2C(H)C(O)PhR 与 CuCl 以等摩尔比反应得到 [Cu(μ-Cl)Ph2P( CH2)nPPh2C(H)C(O)PhR}]2 (n = 1: R = Br (1), OCH3 (2); n = 2: R = Br (3), OCH3 (4))。1 的 X 射线分析表明 Cl 桥连二聚体结构与 P,C 螯合配体。这些化合物的表征通过 FT-IR 和多核 NMR 技术进行。元素分析表明，四种配合物中的叶立德和氯化铜 (I) 之间的化学计量比为 1:1。发现前体配合物 1 和 3 在空气气氛中以中等催化剂负载的 DMF 作为溶剂在 Cu 催化的 Suzuki 交叉偶联反应中表现出高催化活性。