European Journal of Organic Chemistry最新文献

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Regioselective Synthesis of n‐Nonanal and Aldehyde‐Containing Polysiloxanes via Rh‐Catalyzed Hydroformylation Enhanced by A New Silicon‐Tethered Multidentate Phosphine Ligand 一种新型硅系多齿膦配体增强的Rh催化氢甲酰化合成正壬醛和含醛聚硅氧烷的区域选择性
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-04-23 DOI: 10.1002/ejoc.202500020
Shu‐Yuan Tian , Lin Shi , Jun‐Hui Zhu , Dr. Li Li , Dr. Fei Ye , Prof. Dr. Zheng Xu , Prof. Dr. Li‐Wen Xu
{"title":"Regioselective Synthesis of n‐Nonanal and Aldehyde‐Containing Polysiloxanes via Rh‐Catalyzed Hydroformylation Enhanced by A New Silicon‐Tethered Multidentate Phosphine Ligand","authors":"Shu‐Yuan Tian ,&nbsp;Lin Shi ,&nbsp;Jun‐Hui Zhu ,&nbsp;Dr. Li Li ,&nbsp;Dr. Fei Ye ,&nbsp;Prof. Dr. Zheng Xu ,&nbsp;Prof. Dr. Li‐Wen Xu","doi":"10.1002/ejoc.202500020","DOIUrl":"10.1002/ejoc.202500020","url":null,"abstract":"<div><div>Catalytic synthesis of long‐chain alkyl aldehydes presents a significant challenge in homogeneous catalysis and organic synthesis due to the difficulty in regioselective control. Here we report a rhodium‐catalyzed high chemo‐ and regio‐selective hydroformylation of 1‐octene that would be highly useful intermediates in chemical industry. Notably, the easy made tetradentate P‐ligands <strong>L1</strong> and <strong>L2</strong> can effectively suppress hydrogenation and isomerization reaction of olefins and give the desired aldehydes in high yield and good regioselectivity. Control experiments reveal the tetradentate P‐ligands is important for controlling selectivity because the high regioselectivity is found to benefit from the presence of four phosphorus atoms manifesting in the formation of much more efficient coordination interactions to give relatively stable rhodium complexes.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 16","pages":"Article e202500020"},"PeriodicalIF":2.5,"publicationDate":"2025-04-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143192195","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 Multicomponent Synthesis of Six‐Membered Heterocycles 六元杂环的光化学多组分合成
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-04-23 DOI: 10.1002/ejoc.202401480
Dr. Biplob Borah , Mihir Patat , Dr. L. Raju Chowhan
{"title":"Photochemical Multicomponent Synthesis of Six‐Membered Heterocycles","authors":"Dr. Biplob Borah ,&nbsp;Mihir Patat ,&nbsp;Dr. L. Raju Chowhan","doi":"10.1002/ejoc.202401480","DOIUrl":"10.1002/ejoc.202401480","url":null,"abstract":"<div><div>Despite the efficient progress achieved in the synthesis of heterocyclic compounds, accessing these molecules by combining both visible lights induced radical chemistry and multicomponent reactions is extremely demanding yet challenging. Recognizing the significant features associated with oxygen‐ and nitrogen‐containing heterocyclic compounds, the search for these attractive molecules in nature and developing new synthetic strategies for synthesizing these molecules remain interesting domain for synthetic chemists. In this mini‐review article, we aim to demonstrate a transitory outline of the recent development achieved in the synthesis of six‐membered heterocycles having oxygen and nitrogen as the major heteroatoms as well as six‐membered heterocycle containing spirooxindole molecules based on visible‐light‐induced photochemical multicomponent reactions strategies. Besides addressing the key success of the reaction design and product developments in this promising area, we have also emphasized the major shortcomings and challenges associated with the reaction discovery in order to stimulate further succeeding investigations.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 16","pages":"Article e202401480"},"PeriodicalIF":2.5,"publicationDate":"2025-04-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143599704","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
Blue‐Light‐Induced Stereoselective Synthesis of α‐Alkylated Amino Acid Derivatives 蓝光诱导 α-烷基化氨基酸衍生物的立体选择性合成
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-04-23 DOI: 10.1002/ejoc.202401477
Hongying Fan , Meiling Ye , Xue Zhang , Jinyu Hou , Liulin Jiao , Jian Chen , Li Guo , Zhong Lian , Yong Wu
{"title":"Blue‐Light‐Induced Stereoselective Synthesis of α‐Alkylated Amino Acid Derivatives","authors":"Hongying Fan ,&nbsp;Meiling Ye ,&nbsp;Xue Zhang ,&nbsp;Jinyu Hou ,&nbsp;Liulin Jiao ,&nbsp;Jian Chen ,&nbsp;Li Guo ,&nbsp;Zhong Lian ,&nbsp;Yong Wu","doi":"10.1002/ejoc.202401477","DOIUrl":"10.1002/ejoc.202401477","url":null,"abstract":"<div><div>A photoredox‐catalyzed decarboxylative C(<em>sp</em><sup>3</sup>)−H alkylation of glycine derivatives, utilizing (+)/(−)‐camphorsultam as a chiral auxiliary and alkyl <em>N</em>‐hydroxyphthalimide (NHP) ester as a radical precursor, has been developed, providing an efficient approach for the stereoselective synthesis of valuable enantioenriched unnatural <em>α</em>‐alkylated amino acid derivatives. The methodology operates under mild conditions, demonstrates broad substrate tolerance, and exhibits excellent stereoselectivity. Preliminary mechanistic investigations indicate that the reaction proceeds <em>via</em> a radical pathway.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 16","pages":"Article e202401477"},"PeriodicalIF":2.5,"publicationDate":"2025-04-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143666564","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
Photoinduced Copper-Catalyzed N-Arylation Reaction of N–H Heteroarenes Using Aryl Thianthrenium Salts 利用芳基硫鎓盐光诱导N-H杂芳烃的n -芳基化反应
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-04-22 DOI: 10.1002/ejoc.202500303
Zhenhui Wang, Qianqian Yang, Lan Bao, Ruiyun Zhang, Mingming Gao, wei liu
{"title":"Photoinduced Copper-Catalyzed N-Arylation Reaction of N–H Heteroarenes Using Aryl Thianthrenium Salts","authors":"Zhenhui Wang, Qianqian Yang, Lan Bao, Ruiyun Zhang, Mingming Gao, wei liu","doi":"10.1002/ejoc.202500303","DOIUrl":"https://doi.org/10.1002/ejoc.202500303","url":null,"abstract":"Herein, we present an efficient photoinduced copper-catalyzed N-arylation reaction occurring through the cross-coupling of N–H heteroarene with aryl thianthrenium salt (Ar-TTs). This photoactivation strategy exhibits a broad substrate scope, and offers a method for preserving the activated functional groups (such as Br, CHO, and CN) for subsequent derivatizations.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"71 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-04-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143862646","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
Tagitinin C, a Sesquiterpene Lactone, and Derivatives as Proteasome Inhibitors 倍半萜内酯及其衍生物作为蛋白酶体抑制剂
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-04-22 DOI: 10.1002/ejoc.202500181
Georges Massiot, Fadila Derguini, Flavien Marcadet, Fabien Plisson, Raphael Rahmani, Florie Lavigne, Christophe Menendez, Christophe Long
{"title":"Tagitinin C, a Sesquiterpene Lactone, and Derivatives as Proteasome Inhibitors","authors":"Georges Massiot, Fadila Derguini, Flavien Marcadet, Fabien Plisson, Raphael Rahmani, Florie Lavigne, Christophe Menendez, Christophe Long","doi":"10.1002/ejoc.202500181","DOIUrl":"https://doi.org/10.1002/ejoc.202500181","url":null,"abstract":"Tagitinin C, a germacranolide, isolated from Tithonia diversifolia was shown to have an interesting level of activity on the proteasome pathway. It is however a particularly unstable molecule, sensitive to acids, bases, nucleophiles, and light. This article describes a series of modifications aimed at improving the chemical and biological properties of the molecule and securing a solid industrial property. This study particularly focuses on the isobutyrate chain replacement by other esters or ethers. The key steps were the cross-conjugated dienone reactivity neutralization by reduction and the methylene lactone protection with morpholine or imidazole. Selective saponification of the isobutyrate was also achieved with crude pig liver esterase leading to tagitinol C with a moderate yield. Heliangine from the Jerusalem artichoke (Helianthus tuberosus) and hydroxylated derivatives of tagitinin C from the common sunflower (Helianthus annuus), two abundant field crops, constituted alternative sources of germacranolide derivatives not accessible from tagitinin C. Some esters were more potent than the lead compound, whereas the di-ethers displayed higher activity levels, probably due to a better in vivo stability.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"2 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-04-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143858150","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
Front Cover: Investigations into Intramolecular Cerium- and Manganese-Catalyzed Aerobic Coupling of β-Oxoesters with Styryl Moieties (Eur. J. Org. Chem. 15/2025) 封面:分子内铈和锰催化β-氧酯与苯乙烯基部分的好氧偶联的研究。j . Org。化学15/2025)
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-04-22 DOI: 10.1002/ejoc.202581501
M.Sc. Julian Friedrich, Dr. Marc Schmidtmann, Prof. Dr. Jens Christoffers
{"title":"Front Cover: Investigations into Intramolecular Cerium- and Manganese-Catalyzed Aerobic Coupling of β-Oxoesters with Styryl Moieties (Eur. J. Org. Chem. 15/2025)","authors":"M.Sc. Julian Friedrich,&nbsp;Dr. Marc Schmidtmann,&nbsp;Prof. Dr. Jens Christoffers","doi":"10.1002/ejoc.202581501","DOIUrl":"https://doi.org/10.1002/ejoc.202581501","url":null,"abstract":"<p><b>The Front Cover</b> shows two dwarves digging for rare minerals and gemstones in a mine. They are excited when they find crystals of bi- and tricyclic diketones and lactones. The cover image suggests that these very rare structures have crystallized over millions of years in incredible geochemical processes. In contrast to this myth, the products have now been synthesized by manganese-catalyzed oxidative radical cyclizations in an aerobic atmosphere. More information can be found in the Research Article by J. Christoffers and co-workers (DOI: 10.1002/ejoc.202500158). Artwork by Amelie Christoffers.\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":"28 15","pages":""},"PeriodicalIF":2.5,"publicationDate":"2025-04-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.202581501","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143861691","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
Ring-Rearrangement-Driven Formal (3+2) Cycloaddition of Enaminone-Based Thioalkynes with Nitriles to Form Thiazole-Containing Bis-heterocycles 烯酮基硫代炔与腈形成含噻唑的双杂环的环重排驱动的正式(3+2)环加成反应
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-04-22 DOI: 10.1002/ejoc.202500287
Chandran R, Abha Sharma, Keshri Nath Tiwari
{"title":"Ring-Rearrangement-Driven Formal (3+2) Cycloaddition of Enaminone-Based Thioalkynes with Nitriles to Form Thiazole-Containing Bis-heterocycles","authors":"Chandran R, Abha Sharma, Keshri Nath Tiwari","doi":"10.1002/ejoc.202500287","DOIUrl":"https://doi.org/10.1002/ejoc.202500287","url":null,"abstract":"Herein, we report a one-pot synthesis of 3,4-dihydropyridin-2(H)-one containing thiazole derivatives by Bronsted acid-mediated ring-rearrangement and formal (3+2) cycloaddition reaction of enaminone-based thioalkyne with alkyl/aryl nitrile. The developed protocol demonstrates a wide substrate scope for both the reacting partners with high atom-economy furnishing very high to excellent yields of pharmaceutically relevant bis-heterocyclic derivatives. Based on outcome of the product and control experiments, a plausible reaction mechanism has also been proposed. The gram-scale synthesis and further synthetic transformation demonstrate the synthetic efficacy and utility of the developed protocol.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"7 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-04-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143858125","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 Glycoconjugates Containing Selenium and Polyphenols. Stereoselective Synthesis by Pummerer-like Rearrangement 含硒和多酚的新糖缀合物。类振子重排立体选择性合成
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-04-19 DOI: 10.1002/ejoc.202500291
Claudia González, Mauro De Nisco, Reinier Lemos, Giovanna Cimmino, Yoana Pérez-Badell, Severina Pacifico, Silvana Pedatella
{"title":"New Glycoconjugates Containing Selenium and Polyphenols. Stereoselective Synthesis by Pummerer-like Rearrangement","authors":"Claudia González, Mauro De Nisco, Reinier Lemos, Giovanna Cimmino, Yoana Pérez-Badell, Severina Pacifico, Silvana Pedatella","doi":"10.1002/ejoc.202500291","DOIUrl":"https://doi.org/10.1002/ejoc.202500291","url":null,"abstract":"In the last 20 years the exploitation of antioxidant activity of selenobased compounds has improved, just due to the use of Ebselen, a selenocompound, as a Glutathione peroxidase (GPx) mimic. However, their clinical use seems to be compromised by the low solubility in water. To deal with this problem is possible to take advantage of the new approach including selenosugars in which selenium replaces heterocyclic oxygen. In this frame, to optimize the antioxidant properties of selenosugars, the glycoconjugation with a polyphenolic unit, which is a molecule capable of inhibiting or disabling the action of free radicals, has been considered in this work. The Mitsunobu reaction mechanism links covalently the primary alcoholic function of selenobased glycosyl donors, coming from the commercially available d-mannose, and phenolic moiety acceptors, to obtain the corresponding glycoconjugates, has been exploited affording the products in efficient yields. A DFT theoretical study was carried out to help understand the possible influence of the seleno donor on the reactivity. Crucially, a new pathway based on Pummerer-like rearrangement followed by a glycosylation, gave a selenosugar with selenium in the ring and bearing an acetal-like functional group at C-1. All compounds were characterized by NMR spectroscopy confirming their structures and purity.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 7 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-04-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143849458","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
An Efficient Solvent‐Free, Catalyst‐Free Amination on Modified Nucleosides and One‐Pot Three‐Component Synthesis of 1,2,3‐Triazole‐Based Hybrid Nucleosides 改性核苷的高效无溶剂、无催化剂胺化及一锅三组分合成1,2,3 -三唑基杂化核苷
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-04-17 DOI: 10.1002/ejoc.202500203
Samir Kumar Mondal, Shantanu Pal
{"title":"An Efficient Solvent‐Free, Catalyst‐Free Amination on Modified Nucleosides and One‐Pot Three‐Component Synthesis of 1,2,3‐Triazole‐Based Hybrid Nucleosides","authors":"Samir Kumar Mondal, Shantanu Pal","doi":"10.1002/ejoc.202500203","DOIUrl":"https://doi.org/10.1002/ejoc.202500203","url":null,"abstract":"An efficient catalyst‐free, solvent‐free amination reaction has been developed for the synthesis of various bio‐inspired 6‐substituted amino purine nucleoside analogues in good yields. In this sustainable approach, unprotected 6‐substituted aminopurine nucleoside analogues were synthesized via amination reactions of unprotected 6‐Cl purine nucleosides with various amine derivatives. Notably, this method offers a simple, eco‐friendly, unifying protocol for the synthesis of various bioinspired molecules with highly functional group tolerance. Additionally, to demonstrate its synthetic applicability, a one‐pot, three‐component reaction protocol has been shown for the synthesis of novel 1,2,3‐triazole‐attached hybrid nucleoside containing various drug core moieties via click chemistry.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"29 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-04-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143842002","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
Electroreductive Intramolecular Heck‐Type Cyclization for the Synthesis of Benzofused Oxygenated Heterocycles 电还原分子内Heck型环化合成苯并杂环的研究
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-04-17 DOI: 10.1002/ejoc.202500222
Yan Yu, Xin Wang, Yicheng Zhang, Kuai Wang, Ling-Guo Meng
{"title":"Electroreductive Intramolecular Heck‐Type Cyclization for the Synthesis of Benzofused Oxygenated Heterocycles","authors":"Yan Yu, Xin Wang, Yicheng Zhang, Kuai Wang, Ling-Guo Meng","doi":"10.1002/ejoc.202500222","DOIUrl":"https://doi.org/10.1002/ejoc.202500222","url":null,"abstract":"Conventional synthetic routes to benzofused oxygenated heterocycles, such as Dihydrobenzofuran, chromane and isochromane derivatives, often involve complex synthetic conditions, high costs, and environmental concerns. The key to addressing this challenge lies in achieving transition‐metal‐free C(sp²)–I bond cleavage to enable intramolecular radical cyclization. Inspired by electroreductive strategies, we developed a convenient, transition‐metal‐free electroreductive tandem reaction for synthesizing dihydrobenzofuran, chromane, and isochromane derivatives. Comprehensive evaluation demonstrates that our approach not only simplifies synthetic conditions but also suppresses competing hydrogenation and halogenation pathways at the exocyclic carbon radical center.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"14 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-04-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143842003","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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