Journal of Fluorine Chemistry最新文献_第10页

ω-(3-Trifluoromethylpyrazol-4-yl)alkanoic acids via (3 + 2)-cycloaddition of nitrile imines with cyclic enones and deacylative aromatization ω-(3-三氟甲基吡唑-4-基)烷酸通过腈亚胺与环烯酮的(3 + 2)环加成和脱酰芳构化

IF 1.9 4区化学

Journal of Fluorine Chemistry Pub Date : 2023-11-01 DOI: 10.1016/j.jfluchem.2023.110206

Anna Kowalczyk, Greta Utecht-Jarzyńska, Marcin Jasiński

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The double halofluorination reaction of alkynes using trihaloisocyanuric acids and Olah's reagent 用三卤异氰尿酸和奥拉试剂进行炔烃的双卤代氟化反应

IF 1.9 4区化学

Journal of Fluorine Chemistry Pub Date : 2023-11-01 DOI: 10.1016/j.jfluchem.2023.110214

Hugo da S. Bragueroli, Pierre M. Esteves, Marcio C.S. de Mattos

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A concise, greener, and improved scalable process for the preparation of an anti-thrombotic agent, Ticagrelor 一个简洁的，绿色的，改进的可扩展的过程中制备抗血栓剂，替格瑞洛

IF 1.9 4区化学

Journal of Fluorine Chemistry Pub Date : 2023-11-01 DOI: 10.1016/j.jfluchem.2023.110207

V. Ravi Kanth , V. Siddaiah , B. Hanumantha Rao , I. V. Subramanyeswara Rao , J. Venkateswarlu , K. V. V. Prasada Rao

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Study on the fluorination of 1, 2-O-isopropylidene D-pentofuranose with DAST and its scalable application DAST氟化1,2-O-异亚丙基-D-苯并呋喃酮的研究及其应用

IF 1.9 4区化学

Journal of Fluorine Chemistry Pub Date : 2023-10-10 DOI: 10.1016/j.jfluchem.2023.110205

Chunyu Liu , Fazhan Liang , Yu Chen , Xianhua Pan , Zheng Xia

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Multiplicity-edited heteronuclear single quantum coherence experiment modified for 19F-13C 19F-13C的多重编辑杂核单量子相干实验

IF 1.9 4区化学

Journal of Fluorine Chemistry Pub Date : 2023-10-08 DOI: 10.1016/j.jfluchem.2023.110204

Sara A. Maute, Alexander A. Marchione, Elizabeth L. Diaz

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A one-pot radiosynthesis of [18F]FMPEP-d2 for imaging the cannabinoid receptor 1 用于大麻素受体1成像的[18F]FMPEP-d2的一锅放射合成

IF 1.9 4区化学

Journal of Fluorine Chemistry Pub Date : 2023-10-04 DOI: 10.1016/j.jfluchem.2023.110194

Anna Pees , Neil Vasdev

{"title":"A one-pot radiosynthesis of [18F]FMPEP-d2 for imaging the cannabinoid receptor 1","authors":"Anna Pees , Neil Vasdev","doi":"10.1016/j.jfluchem.2023.110194","DOIUrl":"https://doi.org/10.1016/j.jfluchem.2023.110194","url":null,"abstract":"<div>(3R,5R)-5-(3-([18F]fluoromethoxy-d2)phenyl)-3-(((R)-1-phenylethyl)amino)-1-(4-(trifluoromethyl)phenyl)pyrrolidin-2-one ([18F]FMPEP-d2) is a promising positron emission tomography (PET) radiopharmaceutical for the imaging of cannabinoid type 1 receptors in human studies. To facilitate widespread use of [18F]FMPEP-d2 we herein report a simplified one-pot synthesis procedure that is broadly applicable for 18F-fluoromethylation of phenols and can be applied for routine clinical production using a commercial radiofluorination module (GE TRACERlab FX2 N). The present method overcomes previous challenges in the [18F]FMPEP-d2 synthesis related to intermediate purification of a [18F]fluoromethyl building block by using ditosylmethane-d2 and reacting it directly with (3R,5R)-5-(3-hydroxyphenyl)-3-[(R)-1-phenylethylamino]-1-(4-trifluoromethylphenyl)pyrrolidine-2-one in a one-pot nucleophilic reaction with [18F]fluoride (K2CO3, K222, CH3CN, 80 °C, 10 min). After purification of the product by semi-preparative HPLC under isocratic conditions and formulation, [18F]FMPEP-d2 was obtained in a decay-corrected radiochemical yield of 8 ± 1 %, a radiochemical purity >95 % and a molar activity of 322 ± 101 GBq/µmol in a synthesis time of 70 ± 5 min (n = 8). Validation and regulatory submission of [18F]FMPEP-d2 is underway with the new methodology and will facilitate widespread human use as well as multi-center clinical trials.</div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"272 ","pages":"Article 110194"},"PeriodicalIF":1.9,"publicationDate":"2023-10-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41227925","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}

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Fluorination of vanadates with organic fluorinating agents 用有机氟化剂氟化钒酸盐

IF 1.9 4区化学

Journal of Fluorine Chemistry Pub Date : 2023-10-01 DOI: 10.1016/j.jfluchem.2023.110193

Lukáš Krivosudský , Emma Mičejová

{"title":"Fluorination of vanadates with organic fluorinating agents","authors":"Lukáš Krivosudský , Emma Mičejová","doi":"10.1016/j.jfluchem.2023.110193","DOIUrl":"https://doi.org/10.1016/j.jfluchem.2023.110193","url":null,"abstract":"<div>The organic fluorinating agents [bis(2-methoxyethyl)amino]sulfur trifluoride (Deoxo-fluor®), diethylaminosulfur trifluoride (DAST), and N-fluorobenzenesulfonimide (NFSI) were used to inspect the efficiency of fluorination of monovanadate, HxVO4(3−x)− (V1), and decavanadate, HxV10O28(6−x)− (V10), in solution by 51V NMR spectroscopy. It was observed that either VOF4− or VO2F2− can be generated in acetonitrile solutions at room temperature after one hour selectively for HxVO4(3−x)−, while HxV10O28(6−x)− is more sensitive towards reduction and only NFSI can be used to generate VOF4−. The differences in reactivity can be attributed to the electrophilicity of fluorine in Deoxo-fluor® and DAST, and its nucleophilicity in NFSI. Tetrabutylammonium fluoride, triethylamine trifluoride, and hydrogen fluoride–pyridine adduct were also used under the same conditions for comparison of the efficiency and selectivity of fluorination. It was observed that only HF.pyridine provided a complete transformation of V1 and V10 into VOF4−. The pilot experiments introduced in this work are the first example of fluorination of polyoxometalates with organic fluorination agents and other less commonly used fluorides with organic cations and show their great potential in the synthesis of polyoxometalates with fluorido ligand.</div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"271 ","pages":"Article 110193"},"PeriodicalIF":1.9,"publicationDate":"2023-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"92039719","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

Systematic study of nucleophile additions to 1-bromo-4-(trifluorovinyloxy)benzene: A versatile intermediate toward fluorinated ethers of synthetic interest 亲核试剂加在1-溴-4-(三氟乙烯氧基)苯上的系统研究:合成感兴趣的氟化醚的通用中间体

IF 1.9 4区化学

Journal of Fluorine Chemistry Pub Date : 2023-10-01 DOI: 10.1016/j.jfluchem.2023.110187

Scott T. Iacono , Nathan J. Weeks , Dennis W. Smith Jr.

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A straightforward trifluoromethylation at the C6 position of morphinane alkaloids, their modification and evaluation of inhibition of the SARS-CoV-2 main protease 吗啡烷类生物碱C6位的三氟甲基化及其修饰和对SARS-CoV-2主要蛋白酶抑制作用的评价

IF 1.9 4区化学

Journal of Fluorine Chemistry Pub Date : 2023-10-01 DOI: 10.1016/j.jfluchem.2023.110189

Anastasija O. Finke , Vyacheslav I. Krasnov , Tatyana V. Rybalova , Varvara Yu. Chirkova , Svetlana V. Belenkaya , Ekaterina A. Volosnikova , Dmitry N. Shcherbakov , Elvira E. Shults

{"title":"A straightforward trifluoromethylation at the C6 position of morphinane alkaloids, their modification and evaluation of inhibition of the SARS-CoV-2 main protease","authors":"Anastasija O. Finke , Vyacheslav I. Krasnov , Tatyana V. Rybalova , Varvara Yu. Chirkova , Svetlana V. Belenkaya , Ekaterina A. Volosnikova , Dmitry N. Shcherbakov , Elvira E. Shults","doi":"10.1016/j.jfluchem.2023.110189","DOIUrl":"https://doi.org/10.1016/j.jfluchem.2023.110189","url":null,"abstract":"<div>A catalytic trifluoromethylation of stereoisomeric 6-ketomorphinans using Ruppert–Prakash reagent and tetrabutylammonium fluoride (TBAF) was studied. 14β-Hydroxycodeinone, 4-O-methylsinomenine and 1-iodo-4-O-methylsinomenine provided good to excellent yields of the corresponding 6-trifluoromethylated compounds. The new morphinan derivative (6-deoxo-1-iodo-6α-(trifluoromethyl)-4-O-methylsinomenin-6β-ol) was involved in some catalytic transformations for introduction of additional substituent on C-1 position of the morphinan core. The palladium-catalyzed carbonylation–cross coupling reaction of 1-iodo-derivative with phenylacetylene in the presence of PdCl2-(1-Ad)2PBn catalytic system and Mo(CO)6 as a source of carbon monoxide in MeCN proceeds with high selectivity with the formation of alkynyl ketone as the main product. The cyclocondensation with acetamidine hydrochloride afforded the arylpyrimidine – 6α-(trifluoromethyl)-4-O-methylsinomenin-6β-ol hybrid compound. The action of the dehydration system (SOCl2-Py-DMAP) on 6-deoxo-6α-(trifluoromethyl)-4-O-methylsinomenin-6β-ol have led to the formation оf 8β‑chloro-6,7-didehydro-6-(trifluoromethyl)morphinan which showed inhibition the main viral protease (3CLpro) of SARS-CoV-2 at IC50 value of 25 μM.</div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"271 ","pages":"Article 110189"},"PeriodicalIF":1.9,"publicationDate":"2023-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"91957071","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}

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InF3(H2O)2 : An indium fluoride dihydrate phase with direct O-H...F hydrogen bonding between isolated columns of InF4(OH2)2 corner-sharing octahedra InF3(H2O)2:具有直接O-H…的氟化铟二水合物相InF4(OH2)2共用角八面体分离柱间的氢键

IF 1.9 4区化学

Journal of Fluorine Chemistry Pub Date : 2023-10-01 DOI: 10.1016/j.jfluchem.2023.110192

Jean-Paul Laval, Richard Mayet, Julie Cornette

{"title":"InF3(H2O)2 : An indium fluoride dihydrate phase with direct O-H...F hydrogen bonding between isolated columns of InF4(OH2)2 corner-sharing octahedra","authors":"Jean-Paul Laval, Richard Mayet, Julie Cornette","doi":"10.1016/j.jfluchem.2023.110192","DOIUrl":"https://doi.org/10.1016/j.jfluchem.2023.110192","url":null,"abstract":"<div>InF3(H2O)2 is a new monoclinic C2/m phase [a = 5.774(2) Å, b = 10.239(3) Å, c = 4.1150(8) Å, β = 118.16(2)°]. It is obtained fortuitously as very few single crystals during the synthesis in sealed tubes of the phases in the system InF3-TeO2. It can also be prepared by direct dissolution of InF3 or In2O3 in HF 40 %, followed by a slow evaporation of the solution about 50–70 °C. It corresponds to an intermediate unstable dihydrate in the process of hydration of InF3 at air to a stable trihydrate InF3(H2O)3.InF3(H2O)2 structure is composed of trans-chains [InF3(H2O)2]n of InF4(OH2)2 octahedra sharing F vertices, interconnected via strong O<img>H···F hydrogen bonds between equatorial O/F of adjacent chains with short O···F bonds of 2.57 Å and 2.60 Å. A medium range order between F(1) and O(1) equatorial anions is proposed. InF3(H2O)2 seems to be the first simple dihydrate of trivalent metal fluorides. It is compared to InF3(H2O)3 and to other trihydrates presenting some similar structural features.</div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"271 ","pages":"Article 110192"},"PeriodicalIF":1.9,"publicationDate":"2023-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"92030925","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