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Synthesis of Diverse β,β‐Diaryl β‐Siloxy Diamines and Application as Organocatalysts 不同β，β -二芳基β -硅氧烷二胺的合成及其作为有机催化剂的应用
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-07-02 DOI: 10.1002/ejoc.202500624
Satoru Arimitsu, Daiki Tomon, Katsuki Endo, Keidai Takahara
{"title":"Synthesis of Diverse β,β‐Diaryl β‐Siloxy Diamines and Application as Organocatalysts","authors":"Satoru Arimitsu, Daiki Tomon, Katsuki Endo, Keidai Takahara","doi":"10.1002/ejoc.202500624","DOIUrl":"https://doi.org/10.1002/ejoc.202500624","url":null,"abstract":"β,β‐Diaryl‐β‐siloxy diamines were developed as a tunable scaffold for structurally diverse diamine‐based organocatalysts. Synthesis was initiated with the reaction of an oxazolidine methyl ester from L‐serine with various Grignard reagents, introducing a wide range of diaryl substituents at the β‐position. By adjusting the reaction sequence of the silylation and amination steps, the developed synthetic approach enabled the incorporation of diverse aryl, silyl, and amine groups, including cyclic, acyclic tertiary, and secondary amines, into 1,2‐diamines. The resulting diamines were evaluated as catalysts in the enantioselective fluorination of β‐diketones in water using NFSI. Although the yield was similar to that of the conventional catalyst C1, the enantioselectivity was improved, reaching up to 53% ee.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"15 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-07-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144533007","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 Morpholine‐2,5‐diones by Tandem Azido‐Ugi and Ugi Reactions 叠氮- Ugi和Ugi串联反应合成啉- 2,5 -二酮
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-07-01 DOI: 10.1002/ejoc.202500414
Alexander Tsygankov, Tetiana O. Savluk, Vladyslav O. Vereshchak, Svitlana V. Shishkina, Oleksandr V. Buravov, Valentyn A. Chebanov
{"title":"Synthesis of Morpholine‐2,5‐diones by Tandem Azido‐Ugi and Ugi Reactions","authors":"Alexander Tsygankov, Tetiana O. Savluk, Vladyslav O. Vereshchak, Svitlana V. Shishkina, Oleksandr V. Buravov, Valentyn A. Chebanov","doi":"10.1002/ejoc.202500414","DOIUrl":"https://doi.org/10.1002/ejoc.202500414","url":null,"abstract":"3,4‐Disubstituted morpholine‐2,5‐diones containing a tetrazole moiety were unexpected products of a tandem combination of azido‐Ugi and Ugi reactions. The formation of the classical products – Ugi bisamides – was not observed at all in many cases. When the simplest C1‐C3 aliphatic aldehydes were used and the reaction conditions were controlled, their isolation was possible. However, when butanal and pentanal as well as para‐substituted benzaldehydes were used, only products of post‐Ugi transformations, morpholine‐2,5‐diones, could be isolated. The latter could be synthesized either sequentially from the corresponding Ugi bisamides by post‐Ugi transformation or in a one‐pot procedure with prolonged stirring of the reaction mixture of four components – α‐aminomethyltetrazole, aldehyde, monochloroacetic acid and isocyanide. A small targeted library of 15 morpholine‐2,5‐diones containing a tetrazole moiety was obtained by a novel approach. Furthermore, these compounds were able to eliminate the N‐tert‐butyl group from the tetrazole nitrogen in the presence of acid to form the corresponding NH‐unsubstituted tetrazole derivatives of morpholine‐2,5‐diones.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"652 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144533048","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
A C3‐symmetric Diphenylethylendiamine‐Based Catalyst in the Asymmetric Michael Addition of α,β‐Unsaturated Ketones with 4‐Hydroxycoumarin and 4‐Hydroxyquinolin‐2‐one 4 -羟基香豆素和4 -羟基喹啉- 2 -酮对α，β -不饱和酮不对称Michael加成反应的C3对称二苯基乙二胺催化剂
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-07-01 DOI: 10.1002/ejoc.202500338
Alessia CIOGLI, Shilashi Badasa Oljira, Martina De Angelis, Simone Manetto, Francesco Fiorentino, Dante Rotili, Luciana Mosca, Daniel Di Risola, Roberto Mattioli, Marco Pierini, Giulia Mazzoccanti
{"title":"A C3‐symmetric Diphenylethylendiamine‐Based Catalyst in the Asymmetric Michael Addition of α,β‐Unsaturated Ketones with 4‐Hydroxycoumarin and 4‐Hydroxyquinolin‐2‐one","authors":"Alessia CIOGLI, Shilashi Badasa Oljira, Martina De Angelis, Simone Manetto, Francesco Fiorentino, Dante Rotili, Luciana Mosca, Daniel Di Risola, Roberto Mattioli, Marco Pierini, Giulia Mazzoccanti","doi":"10.1002/ejoc.202500338","DOIUrl":"https://doi.org/10.1002/ejoc.202500338","url":null,"abstract":"Even though the amino‐organo catalysis has been known for decades, the use of chiral C3‐symmetric multi–amino catalysts in asymmetric synthesis is not widespread. Herein, we extended the approach previously employed for the chiral 1,2‐diamino‐cyclohexane to the enantiopure 1,2‐diphenylethylendiammine. The independent activity of each catalytic subunit was also confirmed for this enantiopure motif by offline high‐resolution ESI‐MS experiments. We evaluated the advantages and limitations of this novel approach in the asymmetric Michael addition of α/β‐unsaturated ketones to 4‐hydroxycoumarin and 4‐hydroxyquinolin‐2‐one, achieving up to 95% yield and moderate to good stereocontrol (enantiomeric ratio up to 80:20). In the pool of synthetized molecules, there are two novel compounds, and one was prepared for the first time using organocatalysis. In addition, some of these molecules showed an intrinsic scavenging ability on ABTS•+ radical.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"66 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144533008","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 12b‐methyl‐isoindoloisoquinolin‐8‐ones via Iridium‐Catalyzed Intramolecular Hydroarylation of Phenacyl Enamides 铱催化苯酰胺分子内氢芳化合成12b甲基异吲哚-异喹啉- 8
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-06-30 DOI: 10.1002/ejoc.202500451
Wayne Wesley Harding, Ashok R. Gudipally, Hari K. Namballa, Vishwashiv K. Emogaje
{"title":"Synthesis of 12b‐methyl‐isoindoloisoquinolin‐8‐ones via Iridium‐Catalyzed Intramolecular Hydroarylation of Phenacyl Enamides","authors":"Wayne Wesley Harding, Ashok R. Gudipally, Hari K. Namballa, Vishwashiv K. Emogaje","doi":"10.1002/ejoc.202500451","DOIUrl":"https://doi.org/10.1002/ejoc.202500451","url":null,"abstract":"We describe an intramolecular iridium‐catalyzed hydroarylation process for the synthesis of the title scaffold from phenacyl enamide substrates. This method achieves high yields while eliminating the requirement for pre‐functionalized substrates, as compared to Heck‐type cyclization methodologies. Substrate scope and mechanistic studies indicate that the presence of electron‐donating substituents in the incipient ring D moiety is essential for the cyclization, consistent with a pathway involving electrophilic aromatic substitution of iridium in ring D.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"186 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144520492","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
Decarboxylative Alkylation of Difluoroenoxysilanes via Visible Light‐Excited EDA Complex 可见光激发EDA配合物对二氟烯氧基硅烷的脱羧烷基化反应
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-06-30 DOI: 10.1002/ejoc.202500540
Hao Yang, Xinyao Li
{"title":"Decarboxylative Alkylation of Difluoroenoxysilanes via Visible Light‐Excited EDA Complex","authors":"Hao Yang, Xinyao Li","doi":"10.1002/ejoc.202500540","DOIUrl":"https://doi.org/10.1002/ejoc.202500540","url":null,"abstract":"This study presents a visible‐light‐driven, photocatalyst‐free method for synthesizing α,α‐difluoroketones via electron donor‐acceptor (EDA) complex activation. Using cost‐effective aliphatic carboxylic acid derivatives redox‐active esters, the protocol enables decarboxylative difluoroalkylation under mild conditions, achieving high yields (up to 94%) with triphenylamine. Mechanistic studies confirm radical intermediates and a 1:1 EDA complex stoichiometry. The method demonstrates broad substrate scope and successful late‐stage drug modifications, offering a sustainable approach to fluorinated bioactive compounds.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"36 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144520542","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
Organocatalytic Asymmetric Cyclization Reactions with γ‐Hydroxyenones γ -羟基酮的有机催化不对称环化反应
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-06-30 DOI: 10.1002/ejoc.202500482
Megha Balha, Subhas Chandra Pan
{"title":"Organocatalytic Asymmetric Cyclization Reactions with γ‐Hydroxyenones","authors":"Megha Balha, Subhas Chandra Pan","doi":"10.1002/ejoc.202500482","DOIUrl":"https://doi.org/10.1002/ejoc.202500482","url":null,"abstract":"This review article provides an overview of the recent developments in organocatalytic asymmetric cyclization strategies utilizing γ‐hydroxyenones. Due to the bifunctional nature of γ‐hydroxyenones, it is a powerful building block for synthesizing oxygen‐ and nitrogen‐containing heterocycles. The cyclization strategies are systematically categorized based on the nature of the organocatalysts employed: (i) chiral prolinol analogues, which obtain tetrahydrofuran‐fused 3,4‐dihydrocoumarins and 2,3,4‐trisubstituted tetrahydrofurans; (ii) chiral bifunctional squaramides, affording diverse spirocyclic frameworks such as spiro‐tetrahydrofuran‐pyrazolones, morpholinones, and oxindole‐derived systems; (iii) chiral bifunctional thioureas, which forms 1,3‐dioxolanes, oxazolidines, and cyclic acetals; (iv) multifunctional modular organocatalysts, affording enantioenriched α,β‐disubstituted γ‐butyrolactones and (v) other chiral organocatalysts which cannot be grouped in previous categories such as Song’s chiral oligoethylene glycol as a cation‐binding catalyst leads to the generation of chiral 1,4,2‐dioxazinanes.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"62 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144515252","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
I2‐Catalyzed Chemodivergent Synthesis of Dihydrofuro[3,2‐c]coumarins and Pyrano[3,2‐c]coumarins 催化化学发散合成二氢呋喃[3,2‐c]香豆素和吡喃[3,2‐c]香豆素
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-06-30 DOI: 10.1002/ejoc.202500464
Sourav Das, Suvam Paul, Bidisha Dey, Nabajyoti Baildya, Avik Kumar Bagdi
{"title":"I2‐Catalyzed Chemodivergent Synthesis of Dihydrofuro[3,2‐c]coumarins and Pyrano[3,2‐c]coumarins","authors":"Sourav Das, Suvam Paul, Bidisha Dey, Nabajyoti Baildya, Avik Kumar Bagdi","doi":"10.1002/ejoc.202500464","DOIUrl":"https://doi.org/10.1002/ejoc.202500464","url":null,"abstract":"We have developed a chemodivergent protocol for synthesizing furo[3,2‐c]coumarins and pyrano[3,2‐c]coumarins from easily accessible reagents through oxidative cyclization and condensation reaction, respectively. A library of dihydrofuro[3,2‐c]coumarins and pyrano[3,2‐c]coumarins has been synthesized by just tuning the reaction conditions. Moreover, furo[3,2‐c]coumarin could be synthesized through a one‐pot two‐step approach. High chemoselectivity was observed in the case of formation of dihydrofuro[3,2‐c]coumarins. Mild and metal‐free reaction conditions, operational simplicity, use of inexpensive catalyst, broad functional group tolerance, and practicability are the important facets of this strategy. Detailed mechanistic investigation indicated the radical pathway for oxidative cyclization. Whereas, theoretical studies showed that the greater electrophilicity of the carbonyl group in acetonitrile is responsible for the preferential formation of pyrano[3,2‐c]chromen‐5‐ones.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"11 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144520490","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
New Approaches in Catalytic Reactions Using Triphos: A Classical Privileged Ligand | 三磷酸催化反应的新途径：经典特权配体|
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-06-28 DOI: 10.1002/ejoc.202500327
Susan Lühr, Marcelo Vilches-Herrera, Tomás Chávez-Vega, Matías Concha-Puelles
{"title":"New Approaches in Catalytic Reactions Using Triphos: A Classical Privileged Ligand |","authors":"Susan Lühr, Marcelo Vilches-Herrera, Tomás Chávez-Vega, Matías Concha-Puelles","doi":"10.1002/ejoc.202500327","DOIUrl":"https://doi.org/10.1002/ejoc.202500327","url":null,"abstract":"Over the past decades multiple catalytic transformations have been feasible due to the application of triphos as ligand. Its particular fac coordination mode to a transition metal center provides a suitable flexibility enabling variation on the coordination mode resulting in metal stabilization. Most of the reported catalytic reactions have been dominated by the use of the ruthenium‐triphos system, either by application of well‐defined complexes or the in situ formed complex. However, in the last years the emergence of cobalt complexes with comparable or even superior catalytic performance than ruthenium have been reported. In this review we have focused on the use of triphos in selected reactions such as N‐alkylation, formic acid dehydrogenation and bond cleavage.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"644 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144513142","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
Green synthesis of Hantzsch dihydropyridines from biorenewable furans derived from lignocellulosic biomass 从木质纤维素生物质中提取的生物可再生呋喃绿色合成Hantzsch二氢吡啶
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-06-27 DOI: 10.1002/ejoc.202500278
Gabriel Abranches Dias Castro, Lorena Cristina de Andrade Leles, Eduardo Vinícius Vieira Varejão, Felipe Terra Martins, Paula Derksen Macruz, Eduardo Jorge Pilau, Sergio Antonio Fernandes
{"title":"Green synthesis of Hantzsch dihydropyridines from biorenewable furans derived from lignocellulosic biomass","authors":"Gabriel Abranches Dias Castro, Lorena Cristina de Andrade Leles, Eduardo Vinícius Vieira Varejão, Felipe Terra Martins, Paula Derksen Macruz, Eduardo Jorge Pilau, Sergio Antonio Fernandes","doi":"10.1002/ejoc.202500278","DOIUrl":"https://doi.org/10.1002/ejoc.202500278","url":null,"abstract":"Hantzsch dihydropyridines constitute a class of N‐heterocycles with significant pharmacological and technological applications. Due to their importance, the development of new sustainable synthetic methodologies for producing dihydropyridines is of great interest. In this work, we present the synthesis of dihydropyridines via the Hantzsch multicomponent reaction. Furanic aldehydes derived from lignocellulosic biomass are used as substrates, and p‐sulfonic acid calix[4]arene (CX4SO3H) is employed as an organocatalyst, under microwave irradiation (MWI). The furanic compounds were reacted with ethyl acetoacetate and ammonium acetate in the presence of 1.0 mol% of CX4SO3H for 10 minutes at 80 °C under MWI. Twenty‐one dihydropyridines were synthesized in yields ranging from 43% to 96%. Two dihydropyridines were obtained as crystals suitable for X‐ray diffraction analysis, and their crystallographic data are provided. Moreover, the catalytic system can be reused for seven reaction cycles without significant yield loss. The developed methodology offers numerous advantages. It enables the production of dihydropyridines from renewable substrates via a multicomponent reaction in a single step, with a short reaction time. The process uses a reusable organocatalyst and eliminates the need for solvents or metal catalysts.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"22 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144503418","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
Sustainable Synthesis of Biogenic CuO Nanoparticles from Agro‐Waste for One‐Pot C–N Bond Formation 从农业废弃物中可持续合成生物源CuO纳米颗粒用于一锅C-N键形成
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-06-27 DOI: 10.1002/ejoc.202500423
Partha Pratim Sarma, Pranjal K. Baruah
{"title":"Sustainable Synthesis of Biogenic CuO Nanoparticles from Agro‐Waste for One‐Pot C–N Bond Formation","authors":"Partha Pratim Sarma, Pranjal K. Baruah","doi":"10.1002/ejoc.202500423","DOIUrl":"https://doi.org/10.1002/ejoc.202500423","url":null,"abstract":"We report a simple, green, and cost‐effective method for synthesizing copper oxide nanoparticles (CuONPs) using waste cotton shell (WCS) ash extract, which serves as a natural base (pH 12), replacing conventional inorganic bases. The green‐synthesized CuONPs exhibit excellent catalytic activity in heterogenous catalysis facilitating C–N bond formation, a key strategy for accessing various bioactive nitrogen heterocycles. TEM analysis reveals spherical morphology of the CuO nanostructure with an average particle size of 15.5 nm. The catalyst efficiently promotes the synthesis of quinoxaline derivatives via cyclization of terminal alkynes and o‐phenylenediamine, offering broad substrate scope (17 quinoxaline derivatives), good yields, and recyclability. This methodology is also applicable to aliphatic terminal alkynes. Additionally, CuONPs also catalyzed the aza‐Michael addition reactions of amines with α, β‐unsaturated compounds at room temperature, affording excellent yields. The protocol tolerates a wide range of amines, including acyclic, cyclic (up to seven‐membered rings), primary, secondary, and heterocyclic amines. Synthesis of 14 aza Michael addition products are reported. Furthermore, the CuO nanostructures exhibits high stability and reusability for up to five cycles with minimal loss of activity.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"56 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144503466","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
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