两种氟磷苯基化合物的合成及其抑菌活性研究
Syntheses and Antibacterial Activity Study of Two Fluorophosphonylphenyl Compounds
DOI: 10.12677/hjcet.2025.152007, PDF,   
作者: 梁晴雯, 陈 冲, 潘 松, 张千峰*：安徽工业大学分子工程与应用化学研究所，安徽 马鞍山
关键词: 磷氟化合物；磷酰基；抑菌活性；晶体结构；Phosphorus Fluoride Compounds； Phosphoryl Group； Antibacterial Activity； Crystal Structure
摘要: 为设计并合成新的含磷氟键的化合物，并研究其性质，以二苯基氯化膦，苯基二氯化膦为反应物，通过简单的卤素交换反应合成两种化合物PhP(O)F2、Ph2P(O)F，并通过单晶X-射线衍射仪，1H、31P、19F NMR对其结构进行表征。同时对其进行抑菌活性筛选，发现二者对于两种革兰氏菌(大肠杆菌、金黄色葡萄球菌)均具有良好的抑菌活性，并得到了最小抑菌浓度。
Abstract: To design and synthesize new phosphorus-fluorine-containing compounds, and to study their properties, two compounds, PhP(O)F2 and Ph2P(O)F, were synthesized from diphenylphosphine chloride and phenylphosphorus dichloride through a simple halogen exchange reaction. Their structures were characterized by single-crystal X-ray diffraction, 1H, 31P, and 19F NMR spectroscopies. Additionally, their antibacterial activity was screened against two Gram-positive bacteria (Staphylococcus aureus) and Gram-negative bacteria (Escherichia coli), revealing that both compounds exhibited good antibacterial activity with minimum inhibitory concentrations determined.
文章引用：梁晴雯, 陈冲, 潘松, 张千峰. 两种氟磷苯基化合物的合成及其抑菌活性研究[J]. 化学工程与技术, 2025, 15(2): 72-79. https://doi.org/10.12677/hjcet.2025.152007

参考文献

[1] Gouverneur, V. (2024) Fluorine Chemistry: An Outlook to the Future. Advanced Synthesis & Catalysis, 366, 3404-3404. [Google Scholar] [CrossRef] 
[2] Attique, I., Hussain, S., Amjad, M., Nazir, K. and Nazir, M.S. (2020) The Therapeutic and Diagnostic Value of Fluorine. Scientific Inquiry and Review, 4, 17-29. [Google Scholar] [CrossRef] 
[3] Gozdalik, J.T., Adamczyk-Woźniak, A. and Sporzyński, A. (2017) Influence of Fluorine Substituents on the Properties of Phenylboronic Compounds. Pure and Applied Chemistry, 90, 677-702. [Google Scholar] [CrossRef] 
[4] Adamczyk-Woźniak, A., Gozdalik, J.T., Wieczorek, D., Madura, I.D., Kaczorowska, E., Brzezińska, E., et al. (2020) Synthesis, Properties and Antimicrobial Activity of 5-Trifluoromethyl-2-Formylphenylboronic Acid. Molecules, 25, Article 799. [Google Scholar] [CrossRef] [PubMed]
[5] Ravindra, M., Wilson, M.R., Tong, N., O’Connor, C., Karim, M., Polin, L., et al. (2018) Fluorine-Substituted Pyrrolo[2, 3-d]Pyrimidine Analogues with Tumor Targeting via Cellular Uptake by Folate Receptor α and the Proton-Coupled Folate Transporter and Inhibition of de Novo Purine Nucleotide Biosynthesis. Journal of Medicinal Chemistry, 61, 4228-4248. [Google Scholar] [CrossRef] [PubMed]
[6] Partyka, D.V., Washington, M.P., Updegraff, J.B., Chen, X., Incarvito, C.D., Rheingold, A.L., et al. (2009) Surveying the {AuCl} Adducts of Bulky Phosphines Bearing the 2,6-Dimesitylphenyl Group. Journal of Organometallic Chemistry, 694, 1441-1446. [Google Scholar] [CrossRef] 
[7] Huang, Y. and Chen, Q. (2017) Fluorination Reaction of P(Ⅲ) Compounds with the Electrophilic Fluorinating Reagent Selectfluor. Chinese Journal of Organic Chemistry, 37, 2751. [Google Scholar] [CrossRef] 
[8] Kawaguchi, S., Saga, Y., Sato, Y., Minamida, Y., Nomoto, A. and Ogawa, A. (2017) P-Fluorous Phosphines as Electron-Poor/Fluorous Hybrid Functional Ligands for Precious Metal Catalysts: Synthesis of Rh(I), Ir(I), Pt(II), and Au(I) Complexes Bearing P-Fluorous Phosphine Ligands. Inorganics, 5, Article 5. [Google Scholar] [CrossRef] 
[9] Delgado Calvo, F., Mirabello, V., Caporali, M., Oberhauser, W., Raltchev, K., Karaghiosoff, K., et al. (2016) A Straightforward Access to Ruthenium-Coordinated Fluorophosphines from Phosphorous Oxyacids. Dalton Transactions, 45, 2284-2293. [Google Scholar] [CrossRef] [PubMed]
[10] Ullah, E., McNulty, J., Sliwinski, M. and Robertson, A. (2012) Cheminform Abstract: One‐Step Synthesis of Reusable, Polymer‐Supported Trialkyl Phosphine Ligands. Application in Suzuki—Miyaura and Alkoxycarbonylation Reactions. ChemInform, 43, 3990-3993. [Google Scholar] [CrossRef] 
[11] Ullah, E., McNulty, J., Sliwinski, M. and Robertson, A. (2012) One-Step Synthesis of Reusable, Polymer-Supported Tri-Alkyl Phosphine Ligands. Application in Suzuki-Miyaura and Alkoxycarbonylation Reactions. Tetrahedron Letters, 53, 3990-3993. [Google Scholar] [CrossRef] 
[12] Sheldrick, G.M. (2015) SHELXT—Integrated Space-Group and Crystal-Structure Determination. Acta Crystallographica Section A Foundations and Advances, 71, 3-8. [Google Scholar] [CrossRef] [PubMed]
[13] Sheldrick, G. (2014) SHELXT: Integrating Space Group Determination and Structure Solution. Acta Crystallographica Section A Foundations and Advances, 70, C1437-C1437. [Google Scholar] [CrossRef] 
[14] Leão, C., Borges, A. and Simões, M. (2020) NSAIDs as a Drug Repurposing Strategy for Biofilm Control. Antibiotics, 9, Article 591. [Google Scholar] [CrossRef] [PubMed]