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Ball-milling promoted ring-opening selenocyanation of cyclic sulfonium salts with KSeCN 球磨促进环磺酸盐与KSeCN的开环硒氰化反应
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-07-10 DOI: 10.1016/j.tet.2025.134816
Sha Peng, Li Tang, Ni-Dan Meng, Han-Yue Peng, Wen-Shi Yao, Shan-Shan Tang, Li-Hua Yang, Long-Yong Xie
{"title":"Ball-milling promoted ring-opening selenocyanation of cyclic sulfonium salts with KSeCN","authors":"Sha Peng,&nbsp;Li Tang,&nbsp;Ni-Dan Meng,&nbsp;Han-Yue Peng,&nbsp;Wen-Shi Yao,&nbsp;Shan-Shan Tang,&nbsp;Li-Hua Yang,&nbsp;Long-Yong Xie","doi":"10.1016/j.tet.2025.134816","DOIUrl":"10.1016/j.tet.2025.134816","url":null,"abstract":"<div><div>A sustainable and practical method for ball milling-promoted ring-opening selenocyanation of cyclic sulfonium salts using KSeCN has been developed at room temperature under solvent-free conditions. This approach enables the synthesis of a variety of sulfur-containing selenocyanates, demonstrating a broad substrate scope and compatibility with various functional groups. The short reaction time (10–15 min), along with the absence of catalysts, oxidants, and additives, combined with a straightforward work-up procedure that eliminates the need for extraction, renders this method highly efficient and environmentally friendly.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"185 ","pages":"Article 134816"},"PeriodicalIF":2.1,"publicationDate":"2025-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144614024","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
Bispidine moiety-driven simplified eleutherobin analogues: Synthesis and biological evaluation 比斯匹啶驱动的简化刺柳皂苷类似物:合成和生物学评价
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-07-08 DOI: 10.1016/j.tet.2025.134824
Mariia A. Salykina , Alexander S. Bunev , Natalia A. Lozinskaya , Sergey E. Sosonyuk
{"title":"Bispidine moiety-driven simplified eleutherobin analogues: Synthesis and biological evaluation","authors":"Mariia A. Salykina ,&nbsp;Alexander S. Bunev ,&nbsp;Natalia A. Lozinskaya ,&nbsp;Sergey E. Sosonyuk","doi":"10.1016/j.tet.2025.134824","DOIUrl":"10.1016/j.tet.2025.134824","url":null,"abstract":"<div><div>In the present research, the bispidines were used as a scaffold for the design of new inhibitors of protein-protein interaction with potential antitumor activity. Molecular modeling investigation was performed and optimum symmetrical structures demonstrating strong affinity to the taxane binding site in tubulin were determined. The target structures were analyzed retrosynthetically and produced accordingly. A Mannich-type reaction with urotropine and subsequent ring-opening N-acylation constitute the two key steps in the synthetic pathway. The modification options for C9 position in diazabicyclo[3.3.1]nonanes are discussed. The cytotoxicity of the synthesized bispidine derivatives was evaluated on colon cancer HCT116, pulmonary adenocarcinoma A549 and prostatic adenocarcinoma PC-3 cell lines. Three of the obtained compounds showed cytotoxic activity with IC<sub>50</sub> as low as 7.5–15.6 μM.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"185 ","pages":"Article 134824"},"PeriodicalIF":2.1,"publicationDate":"2025-07-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144595499","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
Hexafluoroisopropanol (HFIP)-mediated catalyst-free microwave-assisted novel multicomponent method to access 3-acyl 1,4-diaryl/alkyl pyrroles 六氟异丙醇(HFIP)介导的无催化剂微波辅助新型多组分法获得3-酰基1,4-二芳基/烷基吡咯
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-07-08 DOI: 10.1016/j.tet.2025.134815
Manubolu Guravaiah , Gunna Sampurnamma , Thondooru Sruthi , Vinod D. Jadhav , Bandi Ramakrishna , Raju Doddipalla , Satya Rama Krishna Seemakurti , Vidavalur Siddaiah , Katta Venkateswarlu
{"title":"Hexafluoroisopropanol (HFIP)-mediated catalyst-free microwave-assisted novel multicomponent method to access 3-acyl 1,4-diaryl/alkyl pyrroles","authors":"Manubolu Guravaiah ,&nbsp;Gunna Sampurnamma ,&nbsp;Thondooru Sruthi ,&nbsp;Vinod D. Jadhav ,&nbsp;Bandi Ramakrishna ,&nbsp;Raju Doddipalla ,&nbsp;Satya Rama Krishna Seemakurti ,&nbsp;Vidavalur Siddaiah ,&nbsp;Katta Venkateswarlu","doi":"10.1016/j.tet.2025.134815","DOIUrl":"10.1016/j.tet.2025.134815","url":null,"abstract":"<div><div>It is becoming increasingly common for synthetic chemists to engage in a variety of synthetic transformations using 1,1,1,3,3,3-hexafluoroisopropanol (HFIP), a strong hydrogen bonding-donating, redox-stable polar solvent. Herein, we describe an HFIP-mediated green protocol for the synthesis of novel pyrroles under catalyst-free microwave-assisted conditions. The substituted pyrroles are formed in good to excellent yields (52–99 %) in 1 h from a novel multicomponent reaction of 1-aryl/heteroaryl/alkyl/cycloalkyl substituted 3-(dimethylamino)propenones, aryl/heteroaryl/alkyl/cycloalkyl amines and α-bromo ketones. Furthermore, the structures of products were confirmed by their physical properties, <sup>1</sup>H &amp; <sup>13</sup>C NMR and mass spectral data, and validated by single crystal X-ray diffraction analysis of <strong>4aq</strong> and <strong>4aw</strong>. For the current method, HFIP is recycled and reused. This protocol features catalyst-free conditions, easy recyclability and efficient reusability of HFIP, application of microwaves, ease of handling, short reaction times, high yields of products with vast substrate scope, and preparation of novel pyrroles. This protocol has also been applied for the construction of anticancer agent, 3-aroyl-1,4-diarylpyrrole (ARDAP) (<strong>5</strong>) [with about 8-fold increase of yield and 6.5-fold decrease of time], and a steroid-based complex pyrrole <strong>4bp</strong>.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"185 ","pages":"Article 134815"},"PeriodicalIF":2.1,"publicationDate":"2025-07-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144614023","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 new route to functionalized nitriles, isoxazolines, isoxazoles and hydroximic acids via nitrile oxide generation from secondary nitro compounds 由仲硝基化合物生成氧化腈制备功能化腈、异恶唑、异恶唑和羟肟酸的新途径
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-07-08 DOI: 10.1016/j.tet.2025.134825
Alexander Baranovsky, Yuri Charnou, Peter Kurman, Siarhei Shepialevich
{"title":"A new route to functionalized nitriles, isoxazolines, isoxazoles and hydroximic acids via nitrile oxide generation from secondary nitro compounds","authors":"Alexander Baranovsky,&nbsp;Yuri Charnou,&nbsp;Peter Kurman,&nbsp;Siarhei Shepialevich","doi":"10.1016/j.tet.2025.134825","DOIUrl":"10.1016/j.tet.2025.134825","url":null,"abstract":"<div><div>Acetylation of 2-nitroalcohols under basic conditions mainly results in the cleavage of the C–C-bond and the formation of nitrile oxide. The nitrile oxide can then be trapped by a dipolarofile, solvent or reducing agent. The procedure leads to the formation of ketonitriles, ω-ketoisoxazolines and ketohydroximic acid derivatives.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"185 ","pages":"Article 134825"},"PeriodicalIF":2.1,"publicationDate":"2025-07-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144589288","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 unsymmetrical urea derivatives via domino ring-opening/Pd-catalyzed decarboxylative cross-coupling reaction of isatin-3-oxime and isocyanide 异氰酸酯与异氰酸酯开环/ pd催化脱羧交叉偶联反应合成不对称尿素衍生物
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-07-07 DOI: 10.1016/j.tet.2025.134809
Pooja Soam, Kirti Singh, Parmjeet Kaur, Vikas Tyagi
{"title":"Synthesis of unsymmetrical urea derivatives via domino ring-opening/Pd-catalyzed decarboxylative cross-coupling reaction of isatin-3-oxime and isocyanide","authors":"Pooja Soam,&nbsp;Kirti Singh,&nbsp;Parmjeet Kaur,&nbsp;Vikas Tyagi","doi":"10.1016/j.tet.2025.134809","DOIUrl":"10.1016/j.tet.2025.134809","url":null,"abstract":"<div><div>This study presents a novel palladium-catalyzed method to efficiently synthesize unsymmetrical urea derivatives by domino ring-opening and decarboxylative cross-coupling involving isatin-3-oxime with isocyanides. The optimized protocol demonstrates excellent substrate compatibility, yielding a broad array of urea derivatives in moderate to good yields. A plausible reaction mechanism is proposed which was investigated using various control experiments that revealed key roles of palladium catalysis, offering insights into the ring-opening and decarboxylative coupling steps along with the necessity of free N–H functionality on isatin-3-oxime. Moreover, the synthesized derivatives were further transformed into quinazolinone heterocycles, underscoring their synthetic versatility.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"185 ","pages":"Article 134809"},"PeriodicalIF":2.1,"publicationDate":"2025-07-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144589171","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
[3+2]-cycloaddition reactions of α-trifluoromethyl imino esters with nitrile Imines: Construction of penta-substituted 5-CF3-1,2,4-triazolines [3+2]- α-三氟甲基亚胺酯与腈亚胺的环加成反应:五取代5-CF3-1,2,4-三唑啉的构建
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-07-07 DOI: 10.1016/j.tet.2025.134812
Ying Fan , Ruikang Wang , Gaowang Yang , Peng Jin , Zuyu Bai , Ke-Hu Wang , Danfeng Huang , Yulai Hu
{"title":"[3+2]-cycloaddition reactions of α-trifluoromethyl imino esters with nitrile Imines: Construction of penta-substituted 5-CF3-1,2,4-triazolines","authors":"Ying Fan ,&nbsp;Ruikang Wang ,&nbsp;Gaowang Yang ,&nbsp;Peng Jin ,&nbsp;Zuyu Bai ,&nbsp;Ke-Hu Wang ,&nbsp;Danfeng Huang ,&nbsp;Yulai Hu","doi":"10.1016/j.tet.2025.134812","DOIUrl":"10.1016/j.tet.2025.134812","url":null,"abstract":"<div><div>An efficient [3 + 2]-cycloaddition reaction between <em>α</em>-trifluoromethyl imino esters and di/trifluoromethyl nitrile imines or nonfluorinated nitrile imines generated <em>in-situ</em> from hydrazonoyl halides in the presence of base has been investigated, affording a series of fluoroalkylated penta-substituted 1,2,4-triazolines with a quaternary C5 carbon atom in high yields with excellent regioselectivity under mild conditions. The results show that <em>α</em>-trifluoromethyl imino esters could serve as outstanding dipolarophiles suitable for [3 + 2]-cycloadditions with various fluorinated or non-fluorinated nitrile imines.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"185 ","pages":"Article 134812"},"PeriodicalIF":2.1,"publicationDate":"2025-07-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144579463","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
Transition metal infused magnetic nanocatalysts for the synthesis of biaryls through Suzuki-Miyaura coupling reaction 过渡金属注入磁性纳米催化剂用于Suzuki-Miyaura偶联反应合成双芳烯
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-07-07 DOI: 10.1016/j.tet.2025.134813
Sumanth Hegde , Aakash Venkatesan , Aatika Nizam , Vasantha Veerappa Lakshmaiah , Suresh Babu Naidu Krishna
{"title":"Transition metal infused magnetic nanocatalysts for the synthesis of biaryls through Suzuki-Miyaura coupling reaction","authors":"Sumanth Hegde ,&nbsp;Aakash Venkatesan ,&nbsp;Aatika Nizam ,&nbsp;Vasantha Veerappa Lakshmaiah ,&nbsp;Suresh Babu Naidu Krishna","doi":"10.1016/j.tet.2025.134813","DOIUrl":"10.1016/j.tet.2025.134813","url":null,"abstract":"<div><div>Over the last three decades, there has been a growing interest in the Suzuki-Miyaura cross coupling reaction (SMCR) and its applications. This widely used powerful reaction provides a practical synthetic route for the direct formations of C(sp<sup>2</sup>)-C(sp<sup>2</sup>) bonds. The widespread popularity of Suzuki-Miyaura products highlights the importance of developing regenerable nanocatalysts within comprehensive green synthetic strategies. These nanocatalysts, often utilizing transition metals, provide a valuable route to these products. Increased research focus on regenerable nanocatalysts has led to the design of diverse magnetic nanoparticles, frequently functionalized with transition metals, aiming to optimize reaction efficiency and catalyst recovery. This review covers literature from 2017 onwards, focusing on magnetically separable nanocatalysts, particularly those based on palladium, nickel, cobalt, and copper nanoparticles, for their application in SMCR. A key emphasis is placed on nanocatalysts demonstrating high recyclability without compromising reaction yield.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"185 ","pages":"Article 134813"},"PeriodicalIF":2.1,"publicationDate":"2025-07-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144631099","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
Electrochemical strategies for selective carbohydrate scaffold modification 选择性碳水化合物支架修饰的电化学策略
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-07-07 DOI: 10.1016/j.tet.2025.134814
Pedro J. Tortajada, Helena Lundberg
{"title":"Electrochemical strategies for selective carbohydrate scaffold modification","authors":"Pedro J. Tortajada,&nbsp;Helena Lundberg","doi":"10.1016/j.tet.2025.134814","DOIUrl":"10.1016/j.tet.2025.134814","url":null,"abstract":"<div><div>During the last decade, electrosynthesis has emerged as a highly useful synthetic strategy to access complex organic compounds <em>via</em> intermediate radical species. In the context of carbohydrates, electrochemically driven methods have primarily been used to furnish oxocarbenium ion intermediates for glycosylation reactions. Here, we outline a selection of transformations that take off from this established activation mode and provide new routes to structurally diverse glycan-based compounds under net-oxidative, net-reductive and paired electrolytic conditions.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"185 ","pages":"Article 134814"},"PeriodicalIF":2.1,"publicationDate":"2025-07-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144672092","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
The photocatalytic journey of heteroatoms: Illuminating aza-Henry reactions in organic synthesis 杂原子的光催化之旅:对有机合成中aza-Henry反应的启发
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-07-05 DOI: 10.1016/j.tet.2025.134803
Vishwa K. Patel, Divyani P. Patel, Satish Kumar Singh
{"title":"The photocatalytic journey of heteroatoms: Illuminating aza-Henry reactions in organic synthesis","authors":"Vishwa K. Patel,&nbsp;Divyani P. Patel,&nbsp;Satish Kumar Singh","doi":"10.1016/j.tet.2025.134803","DOIUrl":"10.1016/j.tet.2025.134803","url":null,"abstract":"<div><div>Heteroatoms play a critical role in synthetic chemistry and the development of organic materials, significantly influencing molecular structure and reactivity. This review highlights the pivotal role of heteroatoms in synthetic chemistry and organic materials, with a specific focus on advancements in photocatalyzed aza-Henry reaction in the formation of <em>β</em>-nitroamine compounds. This study emphasizes the aza-Henry reaction, a highly adaptable approach for the synthesis of <em>β</em>-nitroamine compounds, which serve as crucial intermediates in both medicinal and synthetic chemistry. Their unique electronic and steric properties allow for the construction of innovative reagents, catalysts, and materials with applications spanning pharmaceuticals, polymers, and photochemistry. Special attention is given to the role of visible light and heteroatom catalysts in the synthesis of complex nitrogen-containing compounds. This strategy avoids harsh reaction conditions and expands the substrate scope and selectivity by utilizing heteroatom catalysts in conjunction with visible-light activation, offering a sustainable and efficient strategy for the synthesis of structurally diverse <em>β</em>-nitroamine compounds. This approach not only broadens substrate scope but also enhances reaction selectivity, reinforcing its significance in complex molecule synthesis under environmentally benign conditions.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"185 ","pages":"Article 134803"},"PeriodicalIF":2.1,"publicationDate":"2025-07-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144579462","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
One-pot three-component construction of benzo[4,5]imidazo[1,2-a]benzo[4,5]thieno[3,2-d]pyrimidines through [5+1+3] cascade cyclization 通过[5+1+3]级联环化一锅三组分构建苯并[4,5]咪唑[1,2-a]苯并[4,5]噻唑[3,2-d]嘧啶
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-07-05 DOI: 10.1016/j.tet.2025.134811
Jiao Wang, Botao Wang, Ting Shao, Zheng Li
{"title":"One-pot three-component construction of benzo[4,5]imidazo[1,2-a]benzo[4,5]thieno[3,2-d]pyrimidines through [5+1+3] cascade cyclization","authors":"Jiao Wang,&nbsp;Botao Wang,&nbsp;Ting Shao,&nbsp;Zheng Li","doi":"10.1016/j.tet.2025.134811","DOIUrl":"10.1016/j.tet.2025.134811","url":null,"abstract":"<div><div>A one-pot three-component method for the effective construction of 12-arylbenzo[4,5]imidazo[1,2-<em>a</em>]benzo[4,5]thieno[3,2-<em>d</em>]pyrimidines through [5 + 1+3] cascade cyclization of <em>o</em>-nitrochalcones, 2-aminobenzimidazoles, and elemental sulfur is described. The target products are synthesized through the simultaneous formation of two C–S bonds and two C–N bonds. The salient features of this protocol are the use of commercially available starting materials and inexpensive and easy-to-handle solid sulfur source, transition-metal-free condition, wide substrate scope, high yield, and simple workup procedures. The method can also be extended to the synthesis of gram scale.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"185 ","pages":"Article 134811"},"PeriodicalIF":2.1,"publicationDate":"2025-07-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144563058","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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