Journal of Fluorine Chemistry最新文献

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Research on the synthesis of trifluoromethyl-substituted isoquinoline-1,3(2h,4h)-diones via decarboxylative radical addition/cyclization reaction 脱羧自由基加成/环化反应合成三氟甲基取代异喹啉-1,3(2h,4h)-二酮的研究
IF 1.7 4区 化学
Journal of Fluorine Chemistry Pub Date : 2025-07-01 Epub Date: 2025-07-10 DOI: 10.1016/j.jfluchem.2025.110456
Yu Zhang , Bao Feng Du , Jinpeng Miao , Xian Jin Yang
{"title":"Research on the synthesis of trifluoromethyl-substituted isoquinoline-1,3(2h,4h)-diones via decarboxylative radical addition/cyclization reaction","authors":"Yu Zhang ,&nbsp;Bao Feng Du ,&nbsp;Jinpeng Miao ,&nbsp;Xian Jin Yang","doi":"10.1016/j.jfluchem.2025.110456","DOIUrl":"10.1016/j.jfluchem.2025.110456","url":null,"abstract":"<div><div>A transition-metal-free radical addition/cyclization reaction has been developed for the synthesis of Isoquinoline-1,3(2H,4H)‑dione derivatives by the decarboxylation of 3,3,3-trifluoro-2,2-dimethylpropanoic acid and <em>N</em>-methylacrylamide. This mild and convenient method provides a new synthetic route for introducing C(CF<sub>3</sub>)Me<sub>2</sub> group into the Isoquinoline-1,3(2H,4H)‑dione scaffold, which exhibits a wide functional group tolerance and features substrate scope.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"285 ","pages":"Article 110456"},"PeriodicalIF":1.7,"publicationDate":"2025-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144662607","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Engineering perfluoroarene-arene interactions in coumarin-1,2,3-triazole-arene hybrid molecules 香豆素-1,2,3-三唑-芳烃杂化分子中的全氟芳烃-芳烃相互作用
IF 1.7 4区 化学
Journal of Fluorine Chemistry Pub Date : 2025-07-01 Epub Date: 2025-07-06 DOI: 10.1016/j.jfluchem.2025.110453
Abraham Colin-Molina , Jannet Cruz-de la Cruz , David Corona-Becerril , Minerva Rentería-Ortega , Rigoberto Barrios-Francisco
{"title":"Engineering perfluoroarene-arene interactions in coumarin-1,2,3-triazole-arene hybrid molecules","authors":"Abraham Colin-Molina ,&nbsp;Jannet Cruz-de la Cruz ,&nbsp;David Corona-Becerril ,&nbsp;Minerva Rentería-Ortega ,&nbsp;Rigoberto Barrios-Francisco","doi":"10.1016/j.jfluchem.2025.110453","DOIUrl":"10.1016/j.jfluchem.2025.110453","url":null,"abstract":"<div><div>In this work, we describe the synthesis and characterization of five hybrid molecules combining coumarin, 1,2,3-triazole, and arene or perfluoroarene units (compounds <strong>5a, 5b, 6a, 6b</strong>, and <strong>7</strong>). Crystallization conditions of these compounds were explored, and single crystals of compounds <strong>5b</strong> and <strong>7</strong> (as a dioxane solvate, <strong>7<sup>.</sup>DIOX)</strong> were obtained. X-ray diffraction analysis revealed the presence of perfluoroarene–arene (ArF···Ar) interactions that govern the solid-state packing of both structures, leading to rod-like stacking in <strong>5b</strong> and layered arrays in <strong>7·DIOX</strong>. The ArF···Ar contacts were associated with centroid-to-centroid distances between 3.8 and 4.1 Å. Thermal analysis (TGA-DSC) confirmed that all compounds maintain structural integrity at high temperatures; <strong>7·DIOX</strong> retained its crystallinity up to 150 °C before solvent loss. Powder X-ray diffraction confirmed the formation of pure crystalline phases under the employed recrystallization conditions. Additionally, preliminary solid-state fluorescence studies showed modest emission for all coumarin-containing compounds (<strong>5a, 5b</strong>, and <strong>7·DIOX</strong>), with red-shifted maxima and variable quantum yields potentially influenced by non-covalent interactions in their molecular packing. These results underscore the utility of perfluoroarene–arene interactions in directing solid-state organization in fluorinated hybrid molecules.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"285 ","pages":"Article 110453"},"PeriodicalIF":1.7,"publicationDate":"2025-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144595708","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Recent advances in direct 1,2-bis-trifluoro-methylation, -methoxylation, -methylthiolation, and –methylselenylation of unsaturated hydrocarbons 不饱和烃1,2-二-三氟直接甲基化、-甲氧基化、-甲基硫代化和-甲基硒化的最新进展
IF 1.9 4区 化学
Journal of Fluorine Chemistry Pub Date : 2025-07-01 Epub Date: 2025-08-05 DOI: 10.1016/j.jfluchem.2025.110454
Ahmed Kareem Obaid Aldulaimi , Huseyn Imanov , Shakir Mahmood Saeed , Wadhah Hasan Alkhazali , Waam Mohammed Taher , Mariem Alwan , Mahmood Jasem Jawad , Hiba Mushtaq , Esmail Vessally
{"title":"Recent advances in direct 1,2-bis-trifluoro-methylation, -methoxylation, -methylthiolation, and –methylselenylation of unsaturated hydrocarbons","authors":"Ahmed Kareem Obaid Aldulaimi ,&nbsp;Huseyn Imanov ,&nbsp;Shakir Mahmood Saeed ,&nbsp;Wadhah Hasan Alkhazali ,&nbsp;Waam Mohammed Taher ,&nbsp;Mariem Alwan ,&nbsp;Mahmood Jasem Jawad ,&nbsp;Hiba Mushtaq ,&nbsp;Esmail Vessally","doi":"10.1016/j.jfluchem.2025.110454","DOIUrl":"10.1016/j.jfluchem.2025.110454","url":null,"abstract":"<div><div>Owing to its high efficiency, substrate versatility, operational simplicity, and product structure diversity, difunctionalization is a topic of current interest. In this context, some attention has been recently paid to the direct 1,2-bis-trifluorometh(ox)yl(thiol/selenyl)ation of abundant and easily accessible unsaturated hydrocarbons for the single-step construction of biologically important 1,2-bis(trifluoro-methyl/methoxyl/thiol/selenyl)ated compounds. In this Mini-Review, we summarize the recent progress and advances in this attractive field with emphasis on the mechanistic aspect of these reactions.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"285 ","pages":"Article 110454"},"PeriodicalIF":1.9,"publicationDate":"2025-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144771593","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Study on fluorination of didymium oxide [(NdPr)2O3] using ammonium bifluoride (NH4HF2) route 用双氟化铵(NH4HF2)路线氟化氧化二钕[(NdPr)2O3]的研究
IF 1.9 4区 化学
Journal of Fluorine Chemistry Pub Date : 2025-07-01 Epub Date: 2025-07-30 DOI: 10.1016/j.jfluchem.2025.110460
Prafulla S. Sarode, D.N. Ambare, D.K. Sahoo
{"title":"Study on fluorination of didymium oxide [(NdPr)2O3] using ammonium bifluoride (NH4HF2) route","authors":"Prafulla S. Sarode,&nbsp;D.N. Ambare,&nbsp;D.K. Sahoo","doi":"10.1016/j.jfluchem.2025.110460","DOIUrl":"10.1016/j.jfluchem.2025.110460","url":null,"abstract":"<div><div>In the present study, the production of anhydrous didymium fluoride [(NdPr)F<sub>3</sub>] by fluorination of didymium oxide [(NdPr)<sub>2</sub>O<sub>3</sub>] using ammonium bifluoride (NH<sub>4</sub>HF<sub>2</sub>) was investigated. The experimental setup used and the synthesis method as well as the analysis of the product were discussed in detail in the manuscript. Thermogravimetry-differential scanning calorimetry (TG-DSC) technique was employed to identify the mechanism and determine the necessary temperature range for the fluorination reaction. The phase composition of the obtained products (intermediate and final product) were analysed using X-ray diffraction (XRD) analysis. The effects of process parameters such as temperature, composition and reaction time on the fluorination reaction have been studied in detail. Pure anhydrous (NdPr)F<sub>3</sub>, suitable for the production of NdPr metal, was produced under the optimal operating conditions established in this study.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"285 ","pages":"Article 110460"},"PeriodicalIF":1.9,"publicationDate":"2025-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144771592","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Base-mediated [3 + 2] cyclization/rearrangement of N-2,2,2-trifluoroethylisatin ketimines with diethyl azodicarboxylate for construction of spirooxindoles containing trifluoromethyl-1,2,4-triazoles n -2,2,2-三氟乙基化atin酮胺与二乙基偶氮二羧酸酯的碱介导[3 + 2]环化/重排以构建含三氟甲基-1,2,4-三唑的螺菌吲哚
IF 1.7 4区 化学
Journal of Fluorine Chemistry Pub Date : 2025-07-01 Epub Date: 2025-06-30 DOI: 10.1016/j.jfluchem.2025.110452
Yabo Zhang , Liangjun Chen , Wenhe Shi , Panpan Guo , Yan Fu , Ran Guo
{"title":"Base-mediated [3 + 2] cyclization/rearrangement of N-2,2,2-trifluoroethylisatin ketimines with diethyl azodicarboxylate for construction of spirooxindoles containing trifluoromethyl-1,2,4-triazoles","authors":"Yabo Zhang ,&nbsp;Liangjun Chen ,&nbsp;Wenhe Shi ,&nbsp;Panpan Guo ,&nbsp;Yan Fu ,&nbsp;Ran Guo","doi":"10.1016/j.jfluchem.2025.110452","DOIUrl":"10.1016/j.jfluchem.2025.110452","url":null,"abstract":"<div><div>This study descripts a DABCO-mediated tandem [3 + 2] cyclization/rearrangement reaction between <em>N</em>-2,2,2-trifluoroethylisatin ketimines with diethyl azodicarboxylate to successfully synthesize a series of spirooxindoles containing trifluoromethyl-1,2,4-triazoles. This method demonstrates good substrate applicability and achieved up to 92 % yield under mild reaction conditions, which provided an efficient synthetic strategy for the construction of novel spirooxindole-embedded trifluoromethyl triazoles.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"285 ","pages":"Article 110452"},"PeriodicalIF":1.7,"publicationDate":"2025-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144548611","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
PFAS analytical methods – A practical guide PFAS分析方法。实用指南
IF 1.7 4区 化学
Journal of Fluorine Chemistry Pub Date : 2025-07-01 Epub Date: 2025-06-06 DOI: 10.1016/j.jfluchem.2025.110444
Graham K. Ansell, Hassan Javed
{"title":"PFAS analytical methods – A practical guide","authors":"Graham K. Ansell,&nbsp;Hassan Javed","doi":"10.1016/j.jfluchem.2025.110444","DOIUrl":"10.1016/j.jfluchem.2025.110444","url":null,"abstract":"<div><div>The state of the science surrounding per- and polyfluoroalkyl substances (PFAS) has advanced rapidly in recent years, with significant progress made in understanding their physicochemical properties, environmental occurrence, chemistry, and fate and transport. These advancements have been driven by breakthroughs in PFAS analytical capabilities, including the development of robust analytical methods and the availability of higher-resolution instruments. Today, a wide array of PFAS analytical methods exist, with several developed by U.S. federal agencies, including the United States Environmental Protection Agency (USEPA). Additionally, numerous PFAS screening methods have also been developed, primarily for research purposes. This article provides an overview of these methods from a practitioner’s perspective, highlighting their strengths, limitations, and critical caveats to consider when employing them. The aim is to offer a concise guide to PFAS analytical methods, benefiting not only the scientific community but also individuals new to PFAS who are navigating the rapidly evolving regulatory and litigation landscape.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"285 ","pages":"Article 110444"},"PeriodicalIF":1.7,"publicationDate":"2025-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144522199","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Microwave-assisted sodium borohydride/lanthanide rare earth chlorides system for reduction of terminal carboxyl groups in liquid fluoroelastomer 微波辅助硼氢化钠/镧系稀土氯化物体系还原液态氟弹性体末端羧基
IF 1.7 4区 化学
Journal of Fluorine Chemistry Pub Date : 2025-07-01 Epub Date: 2025-07-17 DOI: 10.1016/j.jfluchem.2025.110457
Qi Wang, Ranran Qi, Xiaojie Zhang, Mingyi Liao
{"title":"Microwave-assisted sodium borohydride/lanthanide rare earth chlorides system for reduction of terminal carboxyl groups in liquid fluoroelastomer","authors":"Qi Wang,&nbsp;Ranran Qi,&nbsp;Xiaojie Zhang,&nbsp;Mingyi Liao","doi":"10.1016/j.jfluchem.2025.110457","DOIUrl":"10.1016/j.jfluchem.2025.110457","url":null,"abstract":"<div><div>Liquid terminal carboxyl fluororubber (LTCFs) derived from poly(vinylidene fluoride-co-hexafluoropropylene) was efficiently converted to liquid terminal hydroxyl fluororubber (LTHFs) through a microwave-assisted reduction process employing NaBH<sub>4</sub>/lanthanide chloride (MCl<sub>3</sub>; <em>M</em> = La, Ce, Sm, Gd) catalytic systems. Comprehensive structural characterization via FTIR, UV–Vis, <sup>1</sup>H NMR, GPC, and titration analyses confirmed the transformation of terminal carboxyl groups (-COOH) to hydroxyl groups (-OH) while simultaneously reducing backbone carbon-carbon double bonds (-<em>C</em> = <em>C</em>-) to single bonds (-C-C-). Systematic evaluation revealed NaBH<sub>4</sub>/CeCl<sub>3</sub>, NaBH<sub>4</sub>/SmCl<sub>3</sub>, and NaBH<sub>4</sub>/GdCl<sub>3</sub> systems achieved exceptional reduction efficiencies exceeding 80 %. Process optimization using the NaBH<sub>4</sub>/SmCl<sub>3</sub> system established optimal parameters: 4 min microwave irradiation at 320 W power, SmCl<sub>3</sub>/-COOH molar ratio of 2:1, and substrate/solvent ratio of 1:10 (g/mL), yielding 84.60 % conversion efficiency. The microwave methodology demonstrated remarkable temporal efficiency, achieving &gt;80 % conversion within 4 min compared to conventional thermal methods requiring hours. This accelerated process significantly enhanced reaction kinetics while maintaining structural fidelity, as evidenced by comprehensive spectroscopic and chromatographic analyses. The work establishes a robust microwave-assisted platform for precise fluororubber functional group modification with potential applications in advanced fluoropolymer synthesis.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"285 ","pages":"Article 110457"},"PeriodicalIF":1.7,"publicationDate":"2025-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144655970","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Physicochemical characterization of fluoride solid electrolyte PbSnF4 synthesized via sonochemical reaction 声化学合成氟固体电解质PbSnF4的理化性质
IF 1.7 4区 化学
Journal of Fluorine Chemistry Pub Date : 2025-07-01 Epub Date: 2025-06-27 DOI: 10.1016/j.jfluchem.2025.110450
Meena M , Benson K Money , Amrtha Bhide
{"title":"Physicochemical characterization of fluoride solid electrolyte PbSnF4 synthesized via sonochemical reaction","authors":"Meena M ,&nbsp;Benson K Money ,&nbsp;Amrtha Bhide","doi":"10.1016/j.jfluchem.2025.110450","DOIUrl":"10.1016/j.jfluchem.2025.110450","url":null,"abstract":"<div><div>Demand for batteries with enhanced energy density and improved thermal safety is a key focus for researchers striving to build a sustainable environment. As fluoride ion batteries (FIB) are expected to exhibit high energy density and exceptional thermal stability, research activities are focused on identifying fluoride ion-conducting electrolytes. Among the various fluoride ion conductors, PbSnF<sub>4</sub>, renowned for its superior ionic conductivity, is typically synthesized via mechanochemical reaction. In the present work, PbSnF<sub>4</sub> was synthesized via an acoustic cavitation-driven sonochemical reaction. This novel synthesis route has reduced the duration of the synthesis process to a few minutes compared with several hours for the mechanochemical reaction. The structural, morphological, and ionic transport properties are investigated. The ionic conductivity of the resulting orthorhombic PbSnF<sub>4</sub> is evaluated to be 4.5 × 10⁻<sup>4</sup> S/cm at RT. The contribution of fluoride ions to the total ionic conductivity is estimated via the DC polarization technique as 0.92. The electrochemical stability window (ESW) is measured through cyclic voltammetry (CV) as 0.7 V with PbF<sub>2</sub>/PbSnF<sub>4</sub>/SS cell configuration.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"285 ","pages":"Article 110450"},"PeriodicalIF":1.7,"publicationDate":"2025-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144502610","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Highly diversified fluorinated chromane-thiadiazol-saturated cyclic amine hybrids: Design, synthesis, single crystal XRD and MCF-7 Cell-line Study 高度多样化的氟化铬-噻二唑饱和环胺杂化物:设计、合成、单晶XRD和MCF-7细胞系研究
IF 1.7 4区 化学
Journal of Fluorine Chemistry Pub Date : 2025-07-01 Epub Date: 2025-06-12 DOI: 10.1016/j.jfluchem.2025.110448
Bhavika Mohite , Bhadreshkumar K. Chabhadiya , Nishith Teraiya , Khushal Kapadiya , Ramavatar Meena , Aniruddhasinh Rana , Smita Jauhari
{"title":"Highly diversified fluorinated chromane-thiadiazol-saturated cyclic amine hybrids: Design, synthesis, single crystal XRD and MCF-7 Cell-line Study","authors":"Bhavika Mohite ,&nbsp;Bhadreshkumar K. Chabhadiya ,&nbsp;Nishith Teraiya ,&nbsp;Khushal Kapadiya ,&nbsp;Ramavatar Meena ,&nbsp;Aniruddhasinh Rana ,&nbsp;Smita Jauhari","doi":"10.1016/j.jfluchem.2025.110448","DOIUrl":"10.1016/j.jfluchem.2025.110448","url":null,"abstract":"<div><div>The current study focuses on the synthesis and characterization of novel fluorinated chromane derivatives, aiming to explore their structural and biological potential. The molecular framework integrates fluorine for enhanced physicochemical properties, employing nucleophilic substitution and cyclization strategies. The synthesized derivatives <strong>(4a–4j)</strong> were characterized using advanced spectroscopic methods (<sup>1</sup>H NMR, <sup>19</sup>F NMR, <sup>13</sup>C NMR, and mass spectrometry) and crystallographic analysis, confirming their structural core. Biological evaluations against MCF-7 breast cancer cells revealed significant cytotoxicity, with compounds <strong>4 g</strong> and <strong>4f</strong> demonstrating superior activity (IC<sub>50</sub>: 2.73 µM and 3.81 µM, respectively) compared to the standard sunitinib (IC<sub>50</sub>: 5.00 µM). SAR analysis highlights the role of specific cycloaliphatic and polar substituents in enhancing activity. Additionally, docking studies targeting VEGFR2 elucidated key binding interactions, corroborating the compounds' potential as anticancer agents. This work showed the incorporation of fluorine and the rational design of fluorinated scaffolds for drug development.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"285 ","pages":"Article 110448"},"PeriodicalIF":1.7,"publicationDate":"2025-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144366915","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Pentafluorinated thevinol scaffold for opioid ligands 阿片配体的五氟化醇支架
IF 1.7 4区 化学
Journal of Fluorine Chemistry Pub Date : 2025-07-01 Epub Date: 2025-06-20 DOI: 10.1016/j.jfluchem.2025.110451
Sergey N. Gorlov , Irina V. Sandulenko , Alexander F. Smol'yakov , Аndrey А. Tyutyunov , Maria I. Godovikova , Sergey K. Moiseev
{"title":"Pentafluorinated thevinol scaffold for opioid ligands","authors":"Sergey N. Gorlov ,&nbsp;Irina V. Sandulenko ,&nbsp;Alexander F. Smol'yakov ,&nbsp;Аndrey А. Tyutyunov ,&nbsp;Maria I. Godovikova ,&nbsp;Sergey K. Moiseev","doi":"10.1016/j.jfluchem.2025.110451","DOIUrl":"10.1016/j.jfluchem.2025.110451","url":null,"abstract":"<div><div>An addition reaction of Me<sub>3</sub>SiCF<sub>2</sub>CF<sub>3</sub> to the carbonyl group of thevinal (<strong>10</strong>), a morphinan derivative, followed by an oxidation of the resulting mixture of the C(20)-epimeric secondary alcohols (20<em>R</em>)-<strong>11a</strong> and (20<em>S</em>)-<strong>11b</strong> (15:1) resulted in the first preparation of the pentafluorinated ketone <strong>12</strong>. The latter is expected to serve as a starting compound for the preparation of thevinols and orvinols, putative opioid receptor ligands pentafluorinated within their C(20)-centered pharmacophore. It was shown that MeLi and MeMgI, indeed, add to the carbonyl group of ketone <strong>12</strong> to afford the mixture of C(20)-epimeric tertiary alcohols, pentafluoroethylthevinols, with the 20<em>R</em>-isomer predominating. The reduction of ketone <strong>12</strong> with LiAlH<sub>4</sub> also results in the formation of a mixture of the C(20)-epimeric pentafluorothevinols (20<em>R</em>)-<strong>11a</strong> and (20<em>S</em>)-<strong>11b</strong> However, the ratio of the epimers (1:8) is opposite to that one obtained from the reaction of aldehyde <strong>10</strong> with Me<sub>3</sub>SiCF<sub>2</sub>CF<sub>3</sub>.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"285 ","pages":"Article 110451"},"PeriodicalIF":1.7,"publicationDate":"2025-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144491942","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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