Martin Pošta, Margarita Dmitrieva, Chiara Volpe, Václav Matoušek, Blanka Klepetářová, Petr Beier
Copper(I)-mediated azide-alkyne cycloaddition was coupled with cross-coupling for the synthesis of [6,5,5] ring-fused tricyclic triazoles. Copper(I)-mediated azide-alkyne cycloaddition was investigated on 2-iodoaryl propynes or propynones. With catalytic amount of Cu(I) salts or with N-donor ligands on copper only the products of azide-alkyne cycloadditions were formed. However, with an equimolar amount of copper(I) iodide and triethylamine new [6,5,5] ring-fused tricyclic triazoles were formed by azide-alkyne cycloadditon coupled to a cross-coupling reaction.
{"title":"Synthesis of [6,5,5]Ring-Fused Tricyclic Triazoles by Copper-Promoted Double Cyclization","authors":"Martin Pošta, Margarita Dmitrieva, Chiara Volpe, Václav Matoušek, Blanka Klepetářová, Petr Beier","doi":"10.1002/ejoc.202400736","DOIUrl":"https://doi.org/10.1002/ejoc.202400736","url":null,"abstract":"Copper(I)-mediated azide-alkyne cycloaddition was coupled with cross-coupling for the synthesis of [6,5,5] ring-fused tricyclic triazoles. Copper(I)-mediated azide-alkyne cycloaddition was investigated on 2-iodoaryl propynes or propynones. With catalytic amount of Cu(I) salts or with N-donor ligands on copper only the products of azide-alkyne cycloadditions were formed. However, with an equimolar amount of copper(I) iodide and triethylamine new [6,5,5] ring-fused tricyclic triazoles were formed by azide-alkyne cycloadditon coupled to a cross-coupling reaction.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.8,"publicationDate":"2024-10-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142490804","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}
Andrea M. Escalante, Micaela B. Riera, Mario O. Salazar, Ricardo L.E. Furlan
Traditional methods for discovering bioactive compounds can be time-consuming and resource-intensive, often requiring extensive synthesis and evaluation. To address these challenges, this study combines TLC-based assays with dithioacetal mixture-library preparation, enabling rapid and effective bioactivity screening. Tyrosinase, an enzyme crucial for melanin production and fruit browning, serves as a significant therapeutic target in this context. Despite the substantial potential of sulfur-containing compounds in medicinal chemistry, the use of dithioacetals in drug discovery remains limited. In this study, two small libraries of dithioacetals, comprising more than 150 compounds, were prepared as mixture-libraries and screened on TLC by directly measuring tyrosinase activity on the plate surface. This approach facilitated the efficient preparation and identification of a potent, simple, and readily accessible dithioacetal inhibitor of tyrosinase, with the entire process being conducted on a low milligram scale.
{"title":"Effect-Directed Synthesis of a Dithioacetal Tyrosinase Inhibitor","authors":"Andrea M. Escalante, Micaela B. Riera, Mario O. Salazar, Ricardo L.E. Furlan","doi":"10.1002/ejoc.202401006","DOIUrl":"https://doi.org/10.1002/ejoc.202401006","url":null,"abstract":"Traditional methods for discovering bioactive compounds can be time-consuming and resource-intensive, often requiring extensive synthesis and evaluation. To address these challenges, this study combines TLC-based assays with dithioacetal mixture-library preparation, enabling rapid and effective bioactivity screening. Tyrosinase, an enzyme crucial for melanin production and fruit browning, serves as a significant therapeutic target in this context. Despite the substantial potential of sulfur-containing compounds in medicinal chemistry, the use of dithioacetals in drug discovery remains limited. In this study, two small libraries of dithioacetals, comprising more than 150 compounds, were prepared as mixture-libraries and screened on TLC by directly measuring tyrosinase activity on the plate surface. This approach facilitated the efficient preparation and identification of a potent, simple, and readily accessible dithioacetal inhibitor of tyrosinase, with the entire process being conducted on a low milligram scale.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.8,"publicationDate":"2024-10-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142488770","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}
M. Sc. Madeleine Giraud, M. Sc. Mathis Robin Mitha, M. Sc. Sven Klehenz, Prof. Dr. Hans-Achim Wagenknecht
The Front Cover features an abstract representation of two novel, highly reducing organophotocatalysts derived from N-arylphenothiazines and N,N-diarylphenazines, compounds widely recognized as versatile and effective photoredox catalysts. The catalysts shown are the most efficient from a library of 17 catalysts synthesized. They show remarkable performance in the addition of methanol to α-methylstyrene, which was used as a model reaction, significantly reducing the reaction time and the catalyst loading by more than 20 times. Alongside the featured catalysts, the cover shows abstract representations of photophysical and photocatalytic concepts. The authors used spectroelectrochemistry and DFT calculations to further elucidate their findings and derive structure–activity relationships that might help to further improve organophotocatalysts. More information can be found in the Research Article by H.-A. Wagenknecht and co-workers (DOI: 10.1002/ejoc.202400847).
{"title":"Front Cover: N-Arylphenothiazines and N,N-Diarylphenazines as Tailored Organophotoredox Catalysts for the Reductive Activation of Alkenes (Eur. J. Org. Chem. 40/2024)","authors":"M. Sc. Madeleine Giraud, M. Sc. Mathis Robin Mitha, M. Sc. Sven Klehenz, Prof. Dr. Hans-Achim Wagenknecht","doi":"10.1002/ejoc.202484001","DOIUrl":"10.1002/ejoc.202484001","url":null,"abstract":"<p><b>The Front Cover</b> features an abstract representation of two novel, highly reducing organophotocatalysts derived from <i>N</i>-arylphenothiazines and <i>N</i>,<i>N</i>-diarylphenazines, compounds widely recognized as versatile and effective photoredox catalysts. The catalysts shown are the most efficient from a library of 17 catalysts synthesized. They show remarkable performance in the addition of methanol to α-methylstyrene, which was used as a model reaction, significantly reducing the reaction time and the catalyst loading by more than 20 times. Alongside the featured catalysts, the cover shows abstract representations of photophysical and photocatalytic concepts. The authors used spectroelectrochemistry and DFT calculations to further elucidate their findings and derive structure–activity relationships that might help to further improve organophotocatalysts. More information can be found in the Research Article by H.-A. Wagenknecht and co-workers (DOI: 10.1002/ejoc.202400847).\u0000 <figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure>\u0000 </p>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.5,"publicationDate":"2024-10-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.202484001","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142489826","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}
Montserrat Zidan, Lucas F. Villela, Louis Barriault
Organic transformations initiated by photochemical activation have been at the forefront of reaction discovery. In this study, we present a formal photochemical [3 + 2] and [4 + 2] cycloaddition using N-aryl cyclopropylamines and N-aryl cyclobutylamines in conjunction with α,β-unsaturated carbonyl systems, unveiling two distinct mechanistic pathways. The [3 + 2] cycloaddition is elucidated as being guided by the photochemical activity of an electron donor-acceptor (EDA) complex. Simultaneously, intermolecular [4 + 2] annulation of cyclobutylanilines is achieved by visible-light photoredox catalysis. These simple methodologies have wide applicability, facilitating the synthesis of N-arylaminocycloalkyl compounds in yields ranging from good to excellent
{"title":"Photoactivated Formal [3 + 2] / [4+2] Cycloaddition of N-Aryl Cyclopropyl and Cyclobutylamines","authors":"Montserrat Zidan, Lucas F. Villela, Louis Barriault","doi":"10.1002/ejoc.202400558","DOIUrl":"https://doi.org/10.1002/ejoc.202400558","url":null,"abstract":"Organic transformations initiated by photochemical activation have been at the forefront of reaction discovery. In this study, we present a formal photochemical [3 + 2] and [4 + 2] cycloaddition using N-aryl cyclopropylamines and N-aryl cyclobutylamines in conjunction with α,β-unsaturated carbonyl systems, unveiling two distinct mechanistic pathways. The [3 + 2] cycloaddition is elucidated as being guided by the photochemical activity of an electron donor-acceptor (EDA) complex. Simultaneously, intermolecular [4 + 2] annulation of cyclobutylanilines is achieved by visible-light photoredox catalysis. These simple methodologies have wide applicability, facilitating the synthesis of N-arylaminocycloalkyl compounds in yields ranging from good to excellent","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.8,"publicationDate":"2024-10-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142488769","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}
Herein, a highly efficient five-step reaction sequence to meso-alkyl BODIPYs is presented. In our previous work, the hydroformylation of terminal alkenes was used to generate an aldehyde from an alkene via rhodium catalysis to be employed in a subsequent tandem reaction to obtain BODIPY dyes. However, the use of higher pressures and therefore autoclaves as well as their necessary equipment might limit others to use this method. The refined approach in this work employs ambient pressure hydroformylation, done in a simple Schlenk tube and using a CO/H2 balloon, as key step towards an easier meso-alkyl BODIPY synthesis. Additionally, the use of MTBE instead of chloroform as reaction solvent results in a greener approach. Readily available and easily synthesizable alkenes as well as different pyrrole building blocks can be used to extend the range of known alkyl-BODIPYs. The synthesis of 23 derivatives with overall yields of up to 67% demonstrates the wide applicability and advantages of the refined method.
{"title":"Ambient Pressure Hydroformylation – A Key Step to meso-alkyl BODIPYs","authors":"Bernhard Breit, Lukas Miller, Felix Bauer","doi":"10.1002/ejoc.202401089","DOIUrl":"https://doi.org/10.1002/ejoc.202401089","url":null,"abstract":"Herein, a highly efficient five-step reaction sequence to meso-alkyl BODIPYs is presented. In our previous work, the hydroformylation of terminal alkenes was used to generate an aldehyde from an alkene via rhodium catalysis to be employed in a subsequent tandem reaction to obtain BODIPY dyes. However, the use of higher pressures and therefore autoclaves as well as their necessary equipment might limit others to use this method. The refined approach in this work employs ambient pressure hydroformylation, done in a simple Schlenk tube and using a CO/H2 balloon, as key step towards an easier meso-alkyl BODIPY synthesis. Additionally, the use of MTBE instead of chloroform as reaction solvent results in a greener approach. Readily available and easily synthesizable alkenes as well as different pyrrole building blocks can be used to extend the range of known alkyl-BODIPYs. The synthesis of 23 derivatives with overall yields of up to 67% demonstrates the wide applicability and advantages of the refined method.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.8,"publicationDate":"2024-10-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142487867","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}
Roderick W. Bates, Mikhail Elyashberg, Andrei G. Kutateladze, Craig M. Williams
Using computational methods and comparison of reported NMR data, the reported structure of setosol, an unprecedented benzoxonin fungal natural product, is shown to be incorrect. Setosol is shown to be identical to a known but unnamed diaryl ether.
{"title":"Reassignment of the Structure of Setosol","authors":"Roderick W. Bates, Mikhail Elyashberg, Andrei G. Kutateladze, Craig M. Williams","doi":"10.1002/ejoc.202400431","DOIUrl":"https://doi.org/10.1002/ejoc.202400431","url":null,"abstract":"Using computational methods and comparison of reported NMR data, the reported structure of setosol, an unprecedented benzoxonin fungal natural product, is shown to be incorrect. Setosol is shown to be identical to a known but unnamed diaryl ether.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.8,"publicationDate":"2024-10-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142488771","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}
Duyen K. Nguyen, Tran D. B. Pham, Giang T. H. Tran, Phong D. Nguyen, Truong K. Chau, Khanh T. N. Ong, Anh T. Nguyen, Tung Nguyen
Methods to afford 2-aminobenzothiazoles often involve the use of o-aminothiophenols or aniline-typed precursors. Herein we describe a method to furnish 2-aminobenzothiazoles through the cyclization of o-chloronitrobenzenes and aryl isothiocyanates with the assistance of elemental sulfur. From the perspective of step economy, our strategy allows for the direct use of nitroarene precursors without further reduction to anilines. The scope of the reaction with respect to both substrates was investigated, and it was found that electronic properties of the aryl isothiocyanate was important for obtaining acceptable yields.
{"title":"Elemental Sulfur Promoted Cyclization of o-Chloronitrobenzenes and Aryl Isothiocyanates to Furnish 2-Aminobenzothiazoles","authors":"Duyen K. Nguyen, Tran D. B. Pham, Giang T. H. Tran, Phong D. Nguyen, Truong K. Chau, Khanh T. N. Ong, Anh T. Nguyen, Tung Nguyen","doi":"10.1002/ejoc.202401080","DOIUrl":"https://doi.org/10.1002/ejoc.202401080","url":null,"abstract":"Methods to afford 2-aminobenzothiazoles often involve the use of o-aminothiophenols or aniline-typed precursors. Herein we describe a method to furnish 2-aminobenzothiazoles through the cyclization of o-chloronitrobenzenes and aryl isothiocyanates with the assistance of elemental sulfur. From the perspective of step economy, our strategy allows for the direct use of nitroarene precursors without further reduction to anilines. The scope of the reaction with respect to both substrates was investigated, and it was found that electronic properties of the aryl isothiocyanate was important for obtaining acceptable yields.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.8,"publicationDate":"2024-10-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142487868","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}
Aiming to develop novel annulation reactions using sulfine intermediates, we have established a regioselective formal [2 + 3] cyclization reaction of α-keto sulfines generated from the elimination of arylacyl sulfoxides and thioamides. This new strategy allows for the synthesis of thiazole-5-thiones directly without catalysts or additives. The approach features a step-economic, one-pot characteristics via a tandem sequence of in situα-keto sulfines generation, regiospecifically nucleophilic attack or [3 + 2] cyclizatoin, dithioate (S=C−S−) skeletons formation, and subsequent intramolecular nucleophilic cyclization. This reaction also represents a novel method for constructing dithioate (S=C−S−) skeletons.
{"title":"Regioselective Synthesis of Thiazole-5-thione Based on [2 + 3] Annulation Trapping of α-Keto Sulfine with Thioamide","authors":"Xuehua Zhang, Yingxue Lin, Mingyang Guo, Kewen Xu, Jinhui Zhu, Jun Dong","doi":"10.1002/ejoc.202401056","DOIUrl":"https://doi.org/10.1002/ejoc.202401056","url":null,"abstract":"Aiming to develop novel annulation reactions using sulfine intermediates, we have established a regioselective formal [2 + 3] cyclization reaction of α-keto sulfines generated from the elimination of arylacyl sulfoxides and thioamides. This new strategy allows for the synthesis of thiazole-5-thiones directly without catalysts or additives. The approach features a step-economic, one-pot characteristics via a tandem sequence of in situα-keto sulfines generation, regiospecifically nucleophilic attack or [3 + 2] cyclizatoin, dithioate (S=C−S−) skeletons formation, and subsequent intramolecular nucleophilic cyclization. This reaction also represents a novel method for constructing dithioate (S=C−S−) skeletons.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.8,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142486477","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}
A photo-induced two/three-component radical difluoroethylation or monofluoromethyl sulfonylation of 2-amino aryl ethynes was smoothly finished, which gave a series of difluoroethyl or monofluoromethyl sulfonyl seven-membered N-heterocycles. The two radical systems featured simple/mild reaction conditions, good substrate scopes, and excellent E/Z selectivity. In addition, various radical intermediates were successfully detected by HRMS to explore the reaction process. Single-crystal X-ray diffraction and scaled-up experiments examined the product scaffold and application of this cyclization system.
顺利完成了 2-氨基芳基乙炔的光诱导双/三组分自由基二氟乙基化或单氟甲基磺酰化反应，得到了一系列二氟乙基或单氟甲基磺酰化的七元 N-杂环。这两种自由基体系具有简单/温和的反应条件、良好的底物范围和出色的 E/Z 选择性。此外，还成功地通过 HRMS 检测到了各种自由基中间体，从而探索了反应过程。单晶 X 射线衍射和放大实验研究了该环化体系的产物支架和应用。
{"title":"Photo-Induced Difluoroethylation or Monofluoromethyl Sulfonylation of 2-Amino Aryl Ethynes to Access Diverse Seven-Membered N-Heterocycles","authors":"Yunfei Tian, Luping Zheng, Dongyu Guo, Xinping Ding, Weijun Fu, Zejiang Li","doi":"10.1002/ejoc.202400969","DOIUrl":"https://doi.org/10.1002/ejoc.202400969","url":null,"abstract":"A photo-induced two/three-component radical difluoroethylation or monofluoromethyl sulfonylation of 2-amino aryl ethynes was smoothly finished, which gave a series of difluoroethyl or monofluoromethyl sulfonyl seven-membered N-heterocycles. The two radical systems featured simple/mild reaction conditions, good substrate scopes, and excellent E/Z selectivity. In addition, various radical intermediates were successfully detected by HRMS to explore the reaction process. Single-crystal X-ray diffraction and scaled-up experiments examined the product scaffold and application of this cyclization system.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.8,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142486826","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}
The present study discloses a highly efficient visible-light-induced π-extension of perylene tetraesters and discussion on the regioselectivity in the photocyclization. We initially found that π-extension reaction of 3,4-dimethoxyphenyl perylene tetraester smoothly proceeded by only irradiating blue LED with a complete regioselectivity. Investigations of the photocyclization with various substrates revealed the relationship between the regioselectivity and electron-donating/withdrawing effects of the substituents on the aromatic groups. Moreover, theoretical investigation suggested the importance of bond alteration in the aromatic groups: cyclization proceeds preferentially at shorter C-C bonds with higher double bond characters. The findings will open new possibilities for the practical synthesis of custom-designed π-extended perylene materials.
{"title":"Efficient Visible-Light-Induced π-Extension of Perylene Tetraesters: An Investigation on Regioselectivity","authors":"Keisuke Fujimoto, Shingo Miyano, Kenshin Norizuki, Toshiyasu Inuzuka, Tetsuya Sengoku, Masaki Takahashi","doi":"10.1002/ejoc.202400734","DOIUrl":"https://doi.org/10.1002/ejoc.202400734","url":null,"abstract":"The present study discloses a highly efficient visible-light-induced π-extension of perylene tetraesters and discussion on the regioselectivity in the photocyclization. We initially found that π-extension reaction of 3,4-dimethoxyphenyl perylene tetraester smoothly proceeded by only irradiating blue LED with a complete regioselectivity. Investigations of the photocyclization with various substrates revealed the relationship between the regioselectivity and electron-donating/withdrawing effects of the substituents on the aromatic groups. Moreover, theoretical investigation suggested the importance of bond alteration in the aromatic groups: cyclization proceeds preferentially at shorter C-C bonds with higher double bond characters. The findings will open new possibilities for the practical synthesis of custom-designed π-extended perylene materials.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.8,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142486471","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}
京公网安备 11010802042870号
京ICP备2023020795号-1
扫码关注我们
求助内容：
应助结果提醒方式：