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BODIPY-derived fluorescent probes for targeting and tracking lipid droplets dynamics 用于定位和跟踪脂滴动态的 BODIPY 衍生荧光探针
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-11-01 DOI: 10.1016/j.tet.2024.134354
Javier Ordóñez-Hernández, Fernanda Ferrusca-Martínez, Arturo Jiménez-Sánchez
{"title":"BODIPY-derived fluorescent probes for targeting and tracking lipid droplets dynamics","authors":"Javier Ordóñez-Hernández,&nbsp;Fernanda Ferrusca-Martínez,&nbsp;Arturo Jiménez-Sánchez","doi":"10.1016/j.tet.2024.134354","DOIUrl":"10.1016/j.tet.2024.134354","url":null,"abstract":"<div><div>Lipid droplets (LDs) are ubiquitous intracellular organelles present in various cell types, ranging from adipocytes to cancer cells. Despite their involvement in numerous diseases, current methodologies for monitoring LD dynamics rely primarily on static imaging with a limited selection of fluorescent dyes. In this study, we introduce two novel BODIPY-derived fluorophores designed to facilitate real-time monitoring of LD dynamics. By incorporating triphenylamino (TPA) moieties into the BODIPY core both asymmetrically and symmetrically, we modulated the fluorescence response to the green (GFP) and deep-red (Cy5) confocal channels, respectively, thus allowing dual-channel fluorescence capability for high-resolution, dynamic imaging of LDs within live cells, providing new insights into their behavior.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"168 ","pages":"Article 134354"},"PeriodicalIF":2.1,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142654180","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Transition metal promoted Brook rearrangement and its related reactions 过渡金属促进布鲁克重排及其相关反应
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-10-31 DOI: 10.1016/j.tet.2024.134351
Fazhou Yang, Jinbao Wang, Yujie Dong, Nianci Zhang, Cheng Zhang
{"title":"Transition metal promoted Brook rearrangement and its related reactions","authors":"Fazhou Yang,&nbsp;Jinbao Wang,&nbsp;Yujie Dong,&nbsp;Nianci Zhang,&nbsp;Cheng Zhang","doi":"10.1016/j.tet.2024.134351","DOIUrl":"10.1016/j.tet.2024.134351","url":null,"abstract":"<div><div>The Brook Rearrangement holds significant applications in organic synthesis and has been investigated extensively in past decades. Among the various types of Brook rearrangements, catalytic versions have gained increased attention from the chemical community due to their superior control over stereoselectivity and high reaction efficiency. This review provides a comprehensive summary of recent examples of transition metal-promoted Brook rearrangement and related reactions. It encompasses copper-catalyzed migration of a silyl or boryl group, which represents the most intensively studied reactions, along with zinc-promoted reactions and other transition metal-catalyzed reactions. The substrate scope and reaction mechanisms of these examples are meticulously detailed and analyzed.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"168 ","pages":"Article 134351"},"PeriodicalIF":2.1,"publicationDate":"2024-10-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142578727","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
From blue to red. Reaching the full visible spectrum with a single fluorophore: BODIPY 从蓝色到红色。用单一荧光团达到全可见光谱:BODIPY
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-10-31 DOI: 10.1016/j.tet.2024.134334
José G. Becerra-González , Eduardo Peña-Cabrera , José L. Belmonte-Vázquez
{"title":"From blue to red. Reaching the full visible spectrum with a single fluorophore: BODIPY","authors":"José G. Becerra-González ,&nbsp;Eduardo Peña-Cabrera ,&nbsp;José L. Belmonte-Vázquez","doi":"10.1016/j.tet.2024.134334","DOIUrl":"10.1016/j.tet.2024.134334","url":null,"abstract":"<div><div>BODIPYs (Boron-dipyrromethenes) are a class of fluorophores widely used in a plethora of scientific applications in material science and biomedicine due to their exceptional optical properties. The modulation of the absorption and emission wavelengths of BODIPYs is an area with significant growth opportunities, allowing these compounds to be tailored for specific applications. This review addresses different synthetic strategies that could modify their electronic and optical properties of the BODIPY core, mainly the absorption and emission wavelengths (λ<sub>abs</sub> = 422 nm - λ<sub>emis</sub> = 753 nm and quantum yields up to Φ<sub>c-hex</sub> = 100 %). These methodologies include reactions like nucleophilic substitutions with (chiral/achiral) primary and secondary amines, alkyl/aryl alcohols, active methylenes, as well as Liebeskind-Srogl, Sonogashira, Heck, and Suzuki cross-coupling reactions at the <em>meso</em> and peripheral positions of the BODIPY core. These synthetic strategies incorporate specific functional groups that influence the π-system conjugation, generation of AIEgens, and Donor-Acceptor (D-A) or Donor-Acceptor-Donor (D-A-D) architectures, enabling the labeling of biomolecules such as estrone and tyrosine.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"168 ","pages":"Article 134334"},"PeriodicalIF":2.1,"publicationDate":"2024-10-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142654181","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthesis and properties of β-arylated triphyrins[2.1.1] by successive introduction of one to six aryl groups at the β-pyrrole carbons 通过在 β-吡咯碳原子上连续引入 1 至 6 个芳基,合成 β-芳基化三吡咯[2.1.1] 及其特性
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-10-30 DOI: 10.1016/j.tet.2024.134349
Akrti Sharma, Mangalampalli Ravikanth
{"title":"Synthesis and properties of β-arylated triphyrins[2.1.1] by successive introduction of one to six aryl groups at the β-pyrrole carbons","authors":"Akrti Sharma,&nbsp;Mangalampalli Ravikanth","doi":"10.1016/j.tet.2024.134349","DOIUrl":"10.1016/j.tet.2024.134349","url":null,"abstract":"<div><div>The <em>β</em>-arylated <em>meso</em>-tetra(<em>p</em>-tolyl) triphyrins[2.1.1] containing two, three, and four <em>p</em>-fluorophenyl groups were synthesized by reacting appropriate <em>β</em>-bromo triphyrin[2.1.1] with <em>p</em>-fluorophenyl boronic acid in toluene/THF/H<sub>2</sub>O (1:1:1) at 80 <sup>ο</sup>C for 8 h–12 h and their properties were compared with our previously reported <em>β</em>-arylated triphyrins[2.1.1] containing one and six <em>p</em>-fluorophenyl groups. The increase of the number of <em>p</em>-fluorophenyl groups at the <em>β</em>-pyrrole carbons induces steric hindrance at the periphery of triphyrin[2.1.1] that results in the alteration of electronic properties due to distortion in the macrocycle which is reflected in their structure, spectral and redox properties. The X-ray structure analysis revealed that <em>β</em>-di(<em>p</em>-fluorophenyl) <em>meso</em>-tetra(<em>p</em>-tolyl) triphyrin[2.1.1] was almost planar like <em>meso</em>-tetra(phenyl) triphyrin[2.1.1] whereas the <em>β</em>-hexa(<em>p</em>-fluorophenyl) <em>meso</em>-tetra(<em>p</em>-tolyl) triphyrin[2.1.1] was significantly distorted. The absorption spectra of <em>β</em>-arylated triphyrins[2.1.1] showed bathochromically shifted Soret and Q-bands with reduction in absorption coefficients and increase in the bandwidth compared to the <em>β</em>-unsubstituted <em>meso</em>-tetra(<em>p</em>-tolyl) triphyrin[2.1.1] and the maximum effects were noted for <em>β</em>-hexa(<em>p</em>-fluorophenyl) <em>meso</em>-tetra(<em>p</em>-tolyl) triphyrin[2.1.1]. The <em>β</em>-arylated <em>meso</em>-tetra(<em>p</em>-tolyl) triphyrins[2.1.1] are stable under electrochemical conditions and DFT/TD-DFT studies are in agreement with the experimental observations.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"168 ","pages":"Article 134349"},"PeriodicalIF":2.1,"publicationDate":"2024-10-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142572173","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Heterogeneous synthesis of benzo[f]indole-4,9-diones derivatives using sulfonic resin and photocatalytic study 使用磺酸树脂异构合成苯并[f]吲哚-4,9-二酮衍生物及光催化研究
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-10-29 DOI: 10.1016/j.tet.2024.134337
Salma E. Mora-Rodríguez , Selene Lagunas-Rivera , J. Merced Martínez-Rosales , Yolanda Alcaraz-Contreras , Jorge Alberto Mendoza-Pérez , Miguel A. Vázquez
{"title":"Heterogeneous synthesis of benzo[f]indole-4,9-diones derivatives using sulfonic resin and photocatalytic study","authors":"Salma E. Mora-Rodríguez ,&nbsp;Selene Lagunas-Rivera ,&nbsp;J. Merced Martínez-Rosales ,&nbsp;Yolanda Alcaraz-Contreras ,&nbsp;Jorge Alberto Mendoza-Pérez ,&nbsp;Miguel A. Vázquez","doi":"10.1016/j.tet.2024.134337","DOIUrl":"10.1016/j.tet.2024.134337","url":null,"abstract":"<div><div>This research introduces a heterogeneous approach utilizing a resin-bound sulfonic acid catalyst (Dowex®-H) to synthesize benzo[<em>f</em>]indole-4,9-dione derivatives using β-enaminones systems and 2-bromonaphtoquinone. This method facilitates synthesizing a diverse range of compounds with varying substitution patterns, achieving yields of 88 %. The catalyst can be reused for up to five cycles without requiring reactivation. These compounds absorption spectra also show absorption (<em>λ</em><sub>max</sub>) around 250–260 nm with a significant transition around 400 nm. Their photocatalytic potential was assessed by the model reaction of benzylamine photooxidation, achieving a yield of over 99 % within 36 h.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"168 ","pages":"Article 134337"},"PeriodicalIF":2.1,"publicationDate":"2024-10-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142572171","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Mechanochemical cyclization of push-pull enamines with propargyl alcohols 推拉烯胺与丙炔醇的机械化学环化反应
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-10-29 DOI: 10.1016/j.tet.2024.134339
Srinivasarao Yaragorla, Megavath Vinod, Dandugula Sneha Latha
{"title":"Mechanochemical cyclization of push-pull enamines with propargyl alcohols","authors":"Srinivasarao Yaragorla,&nbsp;Megavath Vinod,&nbsp;Dandugula Sneha Latha","doi":"10.1016/j.tet.2024.134339","DOIUrl":"10.1016/j.tet.2024.134339","url":null,"abstract":"<div><div>We developed an efficient mechanochemical method for the synthesis of 1,2-dihydropyridine derivatives from push-pull enamines and <em>tert</em>-propargyl alcohols under ball milling with <em>p</em>-TsOH/HFIP. The reaction proceeds smoothly under metal-free conditions with fast, efficient, and high-yielding synthesis of 1,2-dihydropyridines. The reaction shows excellent atom economy, with a broad substrate generality.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"168 ","pages":"Article 134339"},"PeriodicalIF":2.1,"publicationDate":"2024-10-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142578731","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Design and synthesis of 3,5-disubstituted isoxazoles by Cu-mediated 1,3-dipolar cycloaddition and their in silico evaluation as potential GABAB receptor modulators 通过铜介导的 1,3-二极环加成法设计和合成 3,5-二取代的异噁唑,并将其作为潜在的 GABAB 受体调节剂进行硅学评估
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-10-29 DOI: 10.1016/j.tet.2024.134336
Zuleyma Martínez-Campos , Francisco José Palacios-Can , Susana T. López-Cortina , Rodrigo Said Razo-Hernández , Mario Fernández-Zertuche
{"title":"Design and synthesis of 3,5-disubstituted isoxazoles by Cu-mediated 1,3-dipolar cycloaddition and their in silico evaluation as potential GABAB receptor modulators","authors":"Zuleyma Martínez-Campos ,&nbsp;Francisco José Palacios-Can ,&nbsp;Susana T. López-Cortina ,&nbsp;Rodrigo Said Razo-Hernández ,&nbsp;Mario Fernández-Zertuche","doi":"10.1016/j.tet.2024.134336","DOIUrl":"10.1016/j.tet.2024.134336","url":null,"abstract":"<div><div>In this work, we report the synthesis of three series of 3,5-disubstituted isoxazoles (<strong>4a-d</strong>, <strong>5a-d</strong> and <strong>6a-d</strong>), as analogues of the clinically important drug baclofen. The isoxazole ring systems were assembled through the key copper-catalyzed 1,3-dipolar cycloaddition reaction between a nitrile oxide (generated <em>in situ</em> from nitro compounds) and an alkyne. An X-ray crystallography study shows that the 1,3-dipolar cycloaddition reactions proceeded with very high regioselectively, leading exclusively to the formation of the 3,5-disubstituted regio isomers. Additionally, it was possible to obtain these compounds in enantiomerically pure form using SuperQuat-type chiral auxiliary. As suggested by our QSAR analysis and docking studies, these analogues have the potential to be biologically active as GABA<sub>B</sub> receptor modulators. Finally, the absorption, distribution, properties of metabolism and excretion (ADME) of the synthesized molecules was also determined by a computational approach. From this work we obtained five molecules ((<em>S</em>)-<strong>4d</strong>, (<em>S</em>)-<strong>5b</strong>, (<em>S</em>)-<strong>6b</strong>, (<em>S</em>)-<strong>6c</strong> and (<em>S</em>)-<strong>6d</strong>) as potential GABA<sub>B</sub> receptor agonists.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"168 ","pages":"Article 134336"},"PeriodicalIF":2.1,"publicationDate":"2024-10-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142578730","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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 efficient synthesis of di-substituted allenes via copper-catalyzed SN2′- substitution reaction of organotitanium reagents with propargyl bromides 通过铜催化有机钛试剂与丙炔溴化物的 SN2′-取代反应高效合成二取代烯烃
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-10-29 DOI: 10.1016/j.tet.2024.134345
Chuan Wu , Li-Rong Han , Jin-Song Hou , Qing-Han Li
{"title":"Highly efficient synthesis of di-substituted allenes via copper-catalyzed SN2′- substitution reaction of organotitanium reagents with propargyl bromides","authors":"Chuan Wu ,&nbsp;Li-Rong Han ,&nbsp;Jin-Song Hou ,&nbsp;Qing-Han Li","doi":"10.1016/j.tet.2024.134345","DOIUrl":"10.1016/j.tet.2024.134345","url":null,"abstract":"<div><div>A simple and mild catalytic S<sub>N</sub>2′-type displacement of propargyl halides with organotitanium reagents is reported. The S<sub>N</sub>2′-type displacement of propargyl bromides with organotitanium reagents mediated by CuI (2 mol%)/MePPh<sub>2</sub>(4 mol%) in dichloro methane afforded multi-substituted allenes in good yields (up to 95 %) at 40 °C for 5 h. The aryls bearing electron-donating or electron-withdrawing groups in aryltitanium reagents gave multi-substituted allenes in good yields. In addition, the di-substituted allenes bearing a naphthyl group was obtained in 54–99 % selectivities with isolated yields of 43–83 %. The process was simple and easily performed, and it provides an efficient method for the synthesis of di-substituted allene derivatives. On the basis of the experimental results, a possible catalytic cycle has been proposed.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"168 ","pages":"Article 134345"},"PeriodicalIF":2.1,"publicationDate":"2024-10-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142654179","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Photochemical generation of ketenes from phenanthrene-based cyclobutanones 菲基环丁酮光化学生成烯酮
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-10-29 DOI: 10.1016/j.tet.2024.134344
Alexander D. Roth, Zhazira Koldasbay, Brett H. Ford, Khaidar Kairbek, Heejoon Ahn, Tarini S. Hardikar, Katherine M. Lane, Sarah M. Haynes, Dasan M. Thamattoor
{"title":"Photochemical generation of ketenes from phenanthrene-based cyclobutanones","authors":"Alexander D. Roth,&nbsp;Zhazira Koldasbay,&nbsp;Brett H. Ford,&nbsp;Khaidar Kairbek,&nbsp;Heejoon Ahn,&nbsp;Tarini S. Hardikar,&nbsp;Katherine M. Lane,&nbsp;Sarah M. Haynes,&nbsp;Dasan M. Thamattoor","doi":"10.1016/j.tet.2024.134344","DOIUrl":"10.1016/j.tet.2024.134344","url":null,"abstract":"<div><div>Various 9,10-cyclopropanated phenanthrenes have been shown previously to be viable photochemical precursors to many different types of carbenes. There is also one known example in the literature of a related approach used to generate diphenylketene from a phenanthrene-derived cyclobutanone in a laser flash photolysis study. In an effort to broaden the scope of this promising yet under-utilized method of ketene generation, the synthesis and characterization of several phenanthrene-based cyclobutanones, and their subsequent photolysis to produce a variety of ketenes, are presented in this report. The ketenes are produced, along with phenanthrene, by a formal 2 + 2 cyclo-reversion of the cyclobutanone moiety and have been intercepted by benzyl alcohol and benzyl amine to form the corresponding benzyl esters and amides respectively.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"168 ","pages":"Article 134344"},"PeriodicalIF":2.1,"publicationDate":"2024-10-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142587330","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Synthesis of reference standards for emerging sulfonamide PFAS precursors suspected in aqueous film-forming foams via a benzyl intermediate 通过苄基中间体合成水成膜泡沫中疑似新出现的磺酰胺类全氟辛烷磺酸(PFAS)前体的标准物质
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-10-29 DOI: 10.1016/j.tet.2024.134347
D. Jérémy Liwara , Anton Pavlov , Jon E. Johansen , Pim E.G. Leonards , Sicco Brandsma , Jacob de Boer , Huiling Liu
{"title":"Synthesis of reference standards for emerging sulfonamide PFAS precursors suspected in aqueous film-forming foams via a benzyl intermediate","authors":"D. Jérémy Liwara ,&nbsp;Anton Pavlov ,&nbsp;Jon E. Johansen ,&nbsp;Pim E.G. Leonards ,&nbsp;Sicco Brandsma ,&nbsp;Jacob de Boer ,&nbsp;Huiling Liu","doi":"10.1016/j.tet.2024.134347","DOIUrl":"10.1016/j.tet.2024.134347","url":null,"abstract":"<div><div>Per- and polyfluoroalkyl substances (PFAS) have been widely studied due to their persistence in the environment and potential risks to wildlife and human health. The identification and analysis of these thousands of compounds in various environmental matrices is crucial for assessing their presence and evaluating potential risks. However, the growing list of suspected PFAS necessitates the synthesis of pure standards, for the development and validation of analytical methods. This study describes the synthesis of ten sulfonamide-based PFAS precursors suspected to be in the environment potentially because of the use of aqueous film forming foams (AFFFs). Starting materials, delivered as isomer mixtures were purified by recrystallization using a benzylamine intermediate as a protecting group. The targeted compounds were obtained by alkylation of this benzyl intermediate followed by a deprotection step using hydrogen and a palladium catalyst. This method was evaluated on different PFAS classes. The ten synthesized compounds, including <em>N</em>-dimethylamminopropyl perfluoroalkane sulfonamides (AmPr-FASA) and <em>N</em>-trimethylammoniopropyl perfluoroalkane sulfonamides (PFASAmS), <em>N</em>-sulfopropyl perfluorohexane sulfonamide (SPr-FHxSA), <em>N</em>-dimethylaminopropyl perfluorohexane sulfonamidopropylsulfate (AmPr-FHxSAPS), <em>N</em>-perfluorobutane sulfonamide (FBSA) and <em>N</em>-perfluorobutane sulfonamidoethanol (FBSE) were characterized by NMR and HRMS. These reference materials will be valuable for developing and validating analytical methods for emerging PFAS in environmental samples.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"169 ","pages":"Article 134347"},"PeriodicalIF":2.1,"publicationDate":"2024-10-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142657409","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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