This work presents a new approach for the oxytrifluoromethylselenolation of olefins using N–SeCF3 saccharin as an electrophilic trifluoromethylselenolation reagent, alcohols as nucleophiles, and dichloromethane as the solvent. The approach employed in mild reaction conditions, free of transition metals and other additives, and showed excellent application to various substrates as well as compatibility with functional groups. A proposed mechanism was investigated by control experiments.
{"title":"Oxytrifluoromethylselenylation of olefins with N–SeCF3 saccharin as trifluoromethylselenylated reagent","authors":"Ke-Yi Xie , Yi-Nuo Zhu , Ming-Hui Shi, Ze-Dong Wang, Cong-Cong Zhang, Zhen-Tao Wang","doi":"10.1016/j.tet.2024.134419","DOIUrl":"10.1016/j.tet.2024.134419","url":null,"abstract":"<div><div>This work presents a new approach for the oxytrifluoromethylselenolation of olefins using <em>N</em>–SeCF<sub>3</sub> saccharin as an electrophilic trifluoromethylselenolation reagent, alcohols as nucleophiles, and dichloromethane as the solvent. The approach employed in mild reaction conditions, free of transition metals and other additives, and showed excellent application to various substrates as well as compatibility with functional groups. A proposed mechanism was investigated by control experiments.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"171 ","pages":"Article 134419"},"PeriodicalIF":2.1,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143181114","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}
An expeditious total synthesis of 3-C-branched rare-sugar monosaccharides dihydrohydroxystreptose, virenose and l-evalose were achieved using l-arabinose as the only key chiral pool starting material. The developed protocol involves the selective protection of hydroxyls and highly stereoselective Grignard reaction at C-3 position of the 3-ulose intermediate.
{"title":"Stereoselective synthesis of dihydrohydroxystreptose, virenose and l-evalose from a common precursor derived from l-arabinose","authors":"Sreevidya Pondla, Praveen Ambati, Kushaal Reddy Aramati, Ramu Sridhar Perali","doi":"10.1016/j.tet.2024.134400","DOIUrl":"10.1016/j.tet.2024.134400","url":null,"abstract":"<div><div>An expeditious total synthesis of 3-<em>C</em>-branched rare-sugar monosaccharides dihydrohydroxystreptose, virenose and <span>l</span>-evalose were achieved using <span>l</span>-arabinose as the only key chiral pool starting material. The developed protocol involves the selective protection of hydroxyls and highly stereoselective Grignard reaction at C-3 position of the 3-ulose intermediate.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"171 ","pages":"Article 134400"},"PeriodicalIF":2.1,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143182048","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}
Pub Date : 2025-01-31DOI: 10.1016/j.tet.2025.134509
Janine Cossy
The introduction of a vinyl group into molecules is of interest as this group can be transformed to different functionalities. In this review, we describe the introduction of a vinyl group in compounds by the formation of C–C bonds, using cross-coupling reactions between (pseudo)halides and vinyl Grignard, vinyllithium and vinylzinc reagents, catalyzed by abundant and cheap transition metals such as iron, cobalt and nickel. In general, the reactions are chemo- and stereoselective.
{"title":"Cross-coupling reactions between vinyl metals and (pseudo)halides induced by earth abundant transition metals (Fe, Co, Ni)","authors":"Janine Cossy","doi":"10.1016/j.tet.2025.134509","DOIUrl":"10.1016/j.tet.2025.134509","url":null,"abstract":"<div><div>The introduction of a vinyl group into molecules is of interest as this group can be transformed to different functionalities. In this review, we describe the introduction of a vinyl group in compounds by the formation of C–C bonds, using cross-coupling reactions between (pseudo)halides and vinyl Grignard, vinyllithium and vinylzinc reagents, catalyzed by abundant and cheap transition metals such as iron, cobalt and nickel. In general, the reactions are chemo- and stereoselective.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"176 ","pages":"Article 134509"},"PeriodicalIF":2.1,"publicationDate":"2025-01-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143519910","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}
Pub Date : 2025-01-31DOI: 10.1016/j.tet.2025.134519
Chao Kan , Chongxun Ge , Song Liu , Song Shi , Hu He , Weike Su
The potential of PARG, the most active dePARylation enzyme, as a therapeutic target lies in its synthetic lethal relationship with other DNA repair genes. The development of PARG inhibitors represents a significant advancement in precision medicine. Currently, no PARG-targeted drugs are available commercially, with the most advanced candidates still in the Phase I clinical trial stage. Herein, we described the route screening and process development for SYN419, a potent PARG inhibitor. The critical imidazo[1,5-a]pyridine core 18 was successfully scaled up to kilogram production. Utilizing 13-step parallel reactions, we obtained the target compound SYN419 and scaled up to tens of grams, quickly fulfilling the material requirement for pre-toxicological study.
{"title":"Efficient synthesis of imidazo[1,5-a]pyridine sulfonamido derivative as a PARG inhibitor","authors":"Chao Kan , Chongxun Ge , Song Liu , Song Shi , Hu He , Weike Su","doi":"10.1016/j.tet.2025.134519","DOIUrl":"10.1016/j.tet.2025.134519","url":null,"abstract":"<div><div>The potential of PARG, the most active dePARylation enzyme, as a therapeutic target lies in its synthetic lethal relationship with other DNA repair genes. The development of PARG inhibitors represents a significant advancement in precision medicine. Currently, no PARG-targeted drugs are available commercially, with the most advanced candidates still in the Phase I clinical trial stage. Herein, we described the route screening and process development for <strong>SYN419</strong>, a potent PARG inhibitor. The critical imidazo[1,5-<em>a</em>]pyridine core <strong>18</strong> was successfully scaled up to kilogram production. Utilizing 13-step parallel reactions, we obtained the target compound <strong>SYN419</strong> and scaled up to tens of grams, quickly fulfilling the material requirement for pre-toxicological study.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"175 ","pages":"Article 134519"},"PeriodicalIF":2.1,"publicationDate":"2025-01-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143360207","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}
Pub Date : 2025-01-30DOI: 10.1016/j.tet.2025.134516
David M. Hodgson
A supposed apocryphal encounter between Robert Robinson and R. B. Woodward was found to be confirmed in Sir Robert’s handwritten memoirs. The current article examines what lay behind this strained meeting of two of the greatest protagonists of organic chemistry from the last century, and its aftermath in the context of what became a race to publish the first total synthesis of a non-aromatic steroid.
{"title":"A brief encounter on steroids between Robinson and Woodward in 1951","authors":"David M. Hodgson","doi":"10.1016/j.tet.2025.134516","DOIUrl":"10.1016/j.tet.2025.134516","url":null,"abstract":"<div><div>A supposed apocryphal encounter between Robert Robinson and R. B. Woodward was found to be confirmed in Sir Robert’s handwritten memoirs. The current article examines what lay behind this strained meeting of two of the greatest protagonists of organic chemistry from the last century, and its aftermath in the context of what became a race to publish the first total synthesis of a non-aromatic steroid.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"176 ","pages":"Article 134516"},"PeriodicalIF":2.1,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143474348","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}
Pub Date : 2025-01-30DOI: 10.1016/j.tet.2025.134515
Dmitrii A. Aksenov , Gilberto E. Fernandez , Iliya K. Kuzminov , Nikolai A. Arutiunov , Elena V. Aleksandrova , Alexander V. Aksenov , Alexandra Vernaza , Jeadyn Ramirez , Kieran Ross , Jadyn L. Smith , Liqin Du , Puppala Sathish , Dean J. Tantillo , Alexander Kornienko
There have been a limited number of reports describing the preparation of 2-(indol-2-yl)-2-arylacetamides and those syntheses that have been published suffer from significant drawbacks. In addition, this class of compounds has not been evaluated biologically despite the occurrence of 2-(indol-2-yl)-acetamides in natural products and medicinally important compounds. We developed a two-step synthesis of these compounds utilizing our previously developed preparation of 2-(3-oxoindolin-ylidene)-2-arylacetonitriles from o-nitroacetophenones and their transformation into the desired compounds utilizing a novel process involving treatment under mild conditions with NaBH4 in EtOH. The synthesized compounds were evaluated for antiproliferative effects against BE(2)-C neuroblastoma cells and two compounds were found to have micromolar IC50 values.
{"title":"Convenient synthesis and antiproliferative activity of 2-(Indol-2-yl)-2-arylacetamides","authors":"Dmitrii A. Aksenov , Gilberto E. Fernandez , Iliya K. Kuzminov , Nikolai A. Arutiunov , Elena V. Aleksandrova , Alexander V. Aksenov , Alexandra Vernaza , Jeadyn Ramirez , Kieran Ross , Jadyn L. Smith , Liqin Du , Puppala Sathish , Dean J. Tantillo , Alexander Kornienko","doi":"10.1016/j.tet.2025.134515","DOIUrl":"10.1016/j.tet.2025.134515","url":null,"abstract":"<div><div>There have been a limited number of reports describing the preparation of 2-(indol-2-yl)-2-arylacetamides and those syntheses that have been published suffer from significant drawbacks. In addition, this class of compounds has not been evaluated biologically despite the occurrence of 2-(indol-2-yl)-acetamides in natural products and medicinally important compounds. We developed a two-step synthesis of these compounds utilizing our previously developed preparation of 2-(3-oxoindolin-ylidene)-2-arylacetonitriles from <em>o</em>-nitroacetophenones and their transformation into the desired compounds utilizing a novel process involving treatment under mild conditions with NaBH<sub>4</sub> in EtOH. The synthesized compounds were evaluated for antiproliferative effects against BE(2)-C neuroblastoma cells and two compounds were found to have micromolar IC<sub>50</sub> values.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"175 ","pages":"Article 134515"},"PeriodicalIF":2.1,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143346712","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}
Pub Date : 2025-01-28DOI: 10.1016/j.tet.2025.134506
Weiwei Yao , Zixi Xie , Xinyu Liu , Zhenpu Wang , Fei Xue , Mengtao Ma
Herein, we report the development of an efficient and straightforward electrochemical oxidation methodology for synthesizing 4-sulfonylisoquinolin-1(2H)-ones. The protocol exhibits remarkable versatility, accommodating a broad substrate scope and tolerating a wide range of functional groups, thereby enabling successful large-scale applications. Preliminary mechanistic studies suggest that the electrochemical oxidation generates an N-radical, which subsequently isomerizes to a C-radical.
{"title":"Controlled Electrochemical C4 Sulfonylation of 1(2H)-isoquinolone derivatives: Through the isomerization of N-radical to C-radical","authors":"Weiwei Yao , Zixi Xie , Xinyu Liu , Zhenpu Wang , Fei Xue , Mengtao Ma","doi":"10.1016/j.tet.2025.134506","DOIUrl":"10.1016/j.tet.2025.134506","url":null,"abstract":"<div><div>Herein, we report the development of an efficient and straightforward electrochemical oxidation methodology for synthesizing 4-sulfonylisoquinolin-1(2<em>H</em>)-ones. The protocol exhibits remarkable versatility, accommodating a broad substrate scope and tolerating a wide range of functional groups, thereby enabling successful large-scale applications. Preliminary mechanistic studies suggest that the electrochemical oxidation generates an N-radical, which subsequently isomerizes to a C-radical.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"174 ","pages":"Article 134506"},"PeriodicalIF":2.1,"publicationDate":"2025-01-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143343120","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}
Pub Date : 2025-01-27DOI: 10.1016/j.tet.2025.134507
Man Zhang , Jia Rui , Chong Yu , Mengyang Sun , Dan Gou , Haifeng Wang , Guangyue Su
Six compounds were isolated from the ethyl acetate extract of the marine fungus Aspergillus japonicas, which was collected from surface seawater in the Arctic 6700-4 sea area, including two new gentisyl alcohol derivatives named dimeric terrestrol I (1) and dimeric terrestrol J (2), along with four known compounds, dimeric terrestrol E (3), 2-(hydroxymethyl) benzene-1,4-diol (4), methyl (2′,5′-dihydroxyphenyl) acetate (5), and toluhydroquinone (6). All compounds were characterized and established by spectral analysis of 1D NMR and reported data, confirmed using 2D NMR and HR-MS for new compounds. All the compounds were tested for in vitro activity. The results show that dimeric terrestrol J (2), alleviated lipopolysaccharide (LPS)-induced BV2 microglial cell death by reducing the generation of nitric oxide (NO), has strong anti-inflammatory activity and is even stronger than Dexamethasone (DEX). Furthermore, molecular docking was conducted to verify the affinity between the protein and ligand.
{"title":"New gentisyl alcohol derivatives from Aspergillus japonicas collected from the Arctic 6700-4 sea area","authors":"Man Zhang , Jia Rui , Chong Yu , Mengyang Sun , Dan Gou , Haifeng Wang , Guangyue Su","doi":"10.1016/j.tet.2025.134507","DOIUrl":"10.1016/j.tet.2025.134507","url":null,"abstract":"<div><div>Six compounds were isolated from the ethyl acetate extract of the marine fungus <em>Aspergillus japonicas</em>, which was collected from surface seawater in the Arctic 6700-4 sea area, including two new gentisyl alcohol derivatives named dimeric terrestrol I (<strong>1</strong>) and dimeric terrestrol J (<strong>2</strong>), along with four known compounds, dimeric terrestrol E (<strong>3</strong>), 2-(hydroxymethyl) benzene-1,4-diol (<strong>4</strong>), methyl (2′,5′-dihydroxyphenyl) acetate (<strong>5</strong>), and toluhydroquinone (<strong>6</strong>). All compounds were characterized and established by spectral analysis of 1D NMR and reported data, confirmed using 2D NMR and HR-MS for new compounds. All the compounds were tested for <em>in vitro</em> activity. The results show that dimeric terrestrol J (<strong>2</strong>), alleviated lipopolysaccharide (LPS)-induced BV2 microglial cell death by reducing the generation of nitric oxide (NO), has strong anti-inflammatory activity and is even stronger than Dexamethasone (DEX). Furthermore, molecular docking was conducted to verify the affinity between the protein and ligand.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"174 ","pages":"Article 134507"},"PeriodicalIF":2.1,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143343116","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}
Pub Date : 2025-01-27DOI: 10.1016/j.tet.2025.134508
Shuting Yin , Fangyao Su , Jinlong Yu , Xixuan Zhao , Yongguo Liu , Sen Liang , Baoguo Sun , Hongyu Tian , Shuang Bai
2-Acetyl-1-pyrroline is the most important flavor compound of rice. However, despite its high practical value as a flavoring compound, its synthesis remains a considerable challenge. This study developed a simplified and practical approach for synthesizing 2-acetyl-1-pyrroline, using methyl prolinate as the starting material through a Grignard reaction of 2-(methoxycarbonyl)-1-pyrroline with MeMgBr in the presence of Et3N/TMSCl or TMSOTf. It was found that adding Et3N/TMSCl or TMSOTf during the Grignard reaction effectively suppresses the formation of the byproduct, the tertiary alcohol 2-(1-hydroxy-1-methylethyl)-1-pyrroline, which results from the excessive addition of the Grignard reagent. This optimized method consistently achieves stable yields of around 50 %. Furthermore, the study analyzes and discusses the formation of an isomer of 2-acetyl-1-pyrroline, specifically 6-methyl-5-oxo-2,3,4,5-tetrahydropyridine, as well as the reactivity of the 2-(methoxycarbonyl)-1-pyrroline intermediate. These findings have important implications for understanding the stability and potential applications of 2-acetyl-1-pyrroline in flavoring.
{"title":"An improved synthesis of 2-acetyl-1-pyrroline via the Grignard reaction in the presence of Et3N/TMSCl","authors":"Shuting Yin , Fangyao Su , Jinlong Yu , Xixuan Zhao , Yongguo Liu , Sen Liang , Baoguo Sun , Hongyu Tian , Shuang Bai","doi":"10.1016/j.tet.2025.134508","DOIUrl":"10.1016/j.tet.2025.134508","url":null,"abstract":"<div><div>2-Acetyl-1-pyrroline is the most important flavor compound of rice. However, despite its high practical value as a flavoring compound, its synthesis remains a considerable challenge. This study developed a simplified and practical approach for synthesizing 2-acetyl-1-pyrroline, using methyl prolinate as the starting material through a Grignard reaction of 2-(methoxycarbonyl)-1-pyrroline with MeMgBr in the presence of Et<sub>3</sub>N/TMSCl or TMSOTf. It was found that adding Et<sub>3</sub>N/TMSCl or TMSOTf during the Grignard reaction effectively suppresses the formation of the byproduct, the tertiary alcohol 2-(1-hydroxy-1-methylethyl)-1-pyrroline, which results from the excessive addition of the Grignard reagent. This optimized method consistently achieves stable yields of around 50 %. Furthermore, the study analyzes and discusses the formation of an isomer of 2-acetyl-1-pyrroline, specifically 6-methyl-5-oxo-2,3,4,5-tetrahydropyridine, as well as the reactivity of the 2-(methoxycarbonyl)-1-pyrroline intermediate. These findings have important implications for understanding the stability and potential applications of 2-acetyl-1-pyrroline in flavoring.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"175 ","pages":"Article 134508"},"PeriodicalIF":2.1,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143360825","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}
Pub Date : 2025-01-26DOI: 10.1016/j.tet.2025.134497
Yan-Ning Niu , Ke-Yu Wang , Feng-Yan Han , Xiao-Feng Xia
Nitrogen-containing dihydroisoquinolin-1(2H)-ones are widely used in various fields, such as medicine, chemical engineering, and materials. The development of novel, mild, and efficient synthetic methods has continuously aroused the interest of synthetic chemists. Recently, the radical addition tandem cyclization strategy has been considered as one of the concise and efficient methods for constructing dihydroisoquinolin-1(2H)-ones. A series of different synthetic methods for synthesizing dihydroisoquinolin-1(2H)-ones through cyclization of N-allylbenzamides with various free radical precursors are surveyed herein, including carbon-centered radicals, phosphorus-centered radicals, sulfur-centered radicals and silicon-centered radicals. The substrate scope and mechanistic details are also discussed.
{"title":"Recent developments for the synthesis of the dihydroisoquinolin-1(2H)-ones via cyclization of N-allylbenzamides","authors":"Yan-Ning Niu , Ke-Yu Wang , Feng-Yan Han , Xiao-Feng Xia","doi":"10.1016/j.tet.2025.134497","DOIUrl":"10.1016/j.tet.2025.134497","url":null,"abstract":"<div><div>Nitrogen-containing dihydroisoquinolin-1(2<em>H</em>)-ones are widely used in various fields, such as medicine, chemical engineering, and materials. The development of novel, mild, and efficient synthetic methods has continuously aroused the interest of synthetic chemists. Recently, the radical addition tandem cyclization strategy has been considered as one of the concise and efficient methods for constructing dihydroisoquinolin-1(2<em>H</em>)-ones. A series of different synthetic methods for synthesizing dihydroisoquinolin-1(2<em>H</em>)-ones through cyclization of <em>N</em>-allylbenzamides with various free radical precursors are surveyed herein, including carbon-centered radicals, phosphorus-centered radicals, sulfur-centered radicals and silicon-centered radicals. The substrate scope and mechanistic details are also discussed.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"174 ","pages":"Article 134497"},"PeriodicalIF":2.1,"publicationDate":"2025-01-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143342867","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}
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