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Phytotoxic neo-clerodane and rearranged neo-clerodane type diterpenoids from Salvia albiflora
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-01-25 DOI: 10.1016/j.tet.2025.134490
Celia Bustos-Brito , Pablo Yair Montaño-Hernández , Omar Salas-Huerta , Daniela Itziguari Ramírez-González , Diana Pérez-Juanchi , Juan Pablo Torres-Medicis , Martha Lydia Macías-Rubalcava , Brenda Y. Bedolla-García , Sergio Zamudio , Leovigildo Quijano , Baldomero Esquivel
{"title":"Phytotoxic neo-clerodane and rearranged neo-clerodane type diterpenoids from Salvia albiflora","authors":"Celia Bustos-Brito ,&nbsp;Pablo Yair Montaño-Hernández ,&nbsp;Omar Salas-Huerta ,&nbsp;Daniela Itziguari Ramírez-González ,&nbsp;Diana Pérez-Juanchi ,&nbsp;Juan Pablo Torres-Medicis ,&nbsp;Martha Lydia Macías-Rubalcava ,&nbsp;Brenda Y. Bedolla-García ,&nbsp;Sergio Zamudio ,&nbsp;Leovigildo Quijano ,&nbsp;Baldomero Esquivel","doi":"10.1016/j.tet.2025.134490","DOIUrl":"10.1016/j.tet.2025.134490","url":null,"abstract":"<div><div>Three previously undescribed diterpenoids (<strong>1</strong>–<strong>3</strong>) were isolated from the leaves of <em>Salvia albiflora</em> Martens &amp; Galeotti and named salbiflorin A (<strong>1</strong>), salbiflorin B (<strong>2</strong>), and deoxysalvisousolide (<strong>3</strong>). Furthermore, six known compounds, including salvixalapadiene (<strong>4</strong>), salvihispin H (<strong>5</strong>), salvisousolide (<strong>6</strong>), tilifodiolide (<strong>7</strong>), salvigenolide (<strong>8</strong>), and 2α-hydroxy-7α-acetoxy-12-oxo-15:16-epoxy-neoclerodan-3,13(16),14-trien-18:19-olide (<strong>9</strong>) were also isolated. The structure and absolute configuration of the new compounds were established primarily through the application of 1D and 2D <sup>1</sup>H and <sup>13</sup>C NMR experiments, HR-DART-MS, and a combination of experimental and theoretical ECD data. Salbiflorin A (<strong>1</strong>) and B (<strong>2</strong>), constitute the first examples of a 9,10-<em>seco</em>-salvileucalane-derived diterpenoids. The phytotoxic activity of compounds <strong>1</strong>−<strong>3</strong>, <strong>6</strong> and <strong>8</strong> was evaluated on the germination and root growth of four weed model species, <em>Amaranthus hypochondriacus</em> L., <em>Panicum miliaceum</em> L., <em>Medicago sativa</em> L., and <em>Trifolium pratense</em> L. Salbiflorin B (<strong>2</strong>) exhibited the highest activity in <em>A. hypocondriacus</em> and <em>T. pratense</em>, with IC<sub>50</sub> values of 115.1 ± 3.14 and 122 ± 2.02 μM, respectively.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"174 ","pages":"Article 134490"},"PeriodicalIF":2.1,"publicationDate":"2025-01-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143343115","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
Prof. Eric Jacobsen and #MSDChemistry: Past, present and future
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-01-25 DOI: 10.1016/j.tet.2025.134498
Rebecca T. Ruck , Petr Vachal
{"title":"Prof. Eric Jacobsen and #MSDChemistry: Past, present and future","authors":"Rebecca T. Ruck ,&nbsp;Petr Vachal","doi":"10.1016/j.tet.2025.134498","DOIUrl":"10.1016/j.tet.2025.134498","url":null,"abstract":"","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"174 ","pages":"Article 134498"},"PeriodicalIF":2.1,"publicationDate":"2025-01-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143343313","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
Recent advancements in catalytic peroxidation of alkenes: Synthetic approach and process optimization
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-01-24 DOI: 10.1016/j.tet.2025.134492
Priteeparna Das, Piyusa Priyadarsan Pattanaik, Rana Chatterjee, Rambabu Dandela
{"title":"Recent advancements in catalytic peroxidation of alkenes: Synthetic approach and process optimization","authors":"Priteeparna Das,&nbsp;Piyusa Priyadarsan Pattanaik,&nbsp;Rana Chatterjee,&nbsp;Rambabu Dandela","doi":"10.1016/j.tet.2025.134492","DOIUrl":"10.1016/j.tet.2025.134492","url":null,"abstract":"<div><div>Di-functionalization of alkene is a compelling area of synthetic interest due to their natural prevalence and significant antimalarial and antimicrobial activities. Nevertheless, chemoselective and regioselective peroxidation of alkenes employing various peroxy reagents is a distinct challenge and equivalent amounts of wastes are generated leading to formation of unwanted by-products and require harsh reaction conditions. On contrary, <em>tert</em>-butyl hydroperoxide (TBHP) associated with relatively high stability of reagent, risk minimization of overly reactive agents, and wide scope of reactions without extreme reactivity. For the first time we have highlighted the recent reports in the catalytic synthesis of acyclic peroxides using TBHP, particularly studied over the period of last 10 years. Also, we have incorporated the insight of metal catalysts and illustrated the reaction mechanism for catalytic peroxidation of various alkenes. The catalytic performance and optimization of reaction parameters are also elucidated.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"174 ","pages":"Article 134492"},"PeriodicalIF":2.1,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143342869","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
Exploration of light mediated strategies in four membered heterocycle synthesis
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-01-24 DOI: 10.1016/j.tet.2025.134493
Suman Majee , Km Anjali , Bimal K. Banik , Devalina Ray
{"title":"Exploration of light mediated strategies in four membered heterocycle synthesis","authors":"Suman Majee ,&nbsp;Km Anjali ,&nbsp;Bimal K. Banik ,&nbsp;Devalina Ray","doi":"10.1016/j.tet.2025.134493","DOIUrl":"10.1016/j.tet.2025.134493","url":null,"abstract":"","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"174 ","pages":"Article 134493"},"PeriodicalIF":2.1,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143342944","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 and functionalization of 2-iodoimidazo[1,2-a]pyridines in palladium-catalysed amino-, aryloxy- and alkoxycarbonylations
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-01-23 DOI: 10.1016/j.tet.2025.134489
Péter Szuroczki , Laura Barbara Jenei , Viktor Sándor , Attila Bényei , László Kollár
{"title":"Synthesis and functionalization of 2-iodoimidazo[1,2-a]pyridines in palladium-catalysed amino-, aryloxy- and alkoxycarbonylations","authors":"Péter Szuroczki ,&nbsp;Laura Barbara Jenei ,&nbsp;Viktor Sándor ,&nbsp;Attila Bényei ,&nbsp;László Kollár","doi":"10.1016/j.tet.2025.134489","DOIUrl":"10.1016/j.tet.2025.134489","url":null,"abstract":"<div><div>Imidazo[1,2-<em>a</em>]pyridines possessing carboxamido and ester functionalities in 2- and 6-positions were synthesised in palladium-catalysed amino- and alkoxy/aryloxycarbonylation using a great variety of amines and alcohols/phenols as <em>N</em>- and <em>O</em>-nucleophiles, respectively. The corresponding iodoheteroaromatics, used as substrates, were synthesised from the substituted 2-aminopyridines, terminal alkynes and iodine in copper-catalysed oxidative ring-closure─iodination reaction sequence. Mono- and dinuclear copper-2-aminopyridine complexes, used as pre-formed catalysts, were characterised by X-ray crystallography. The amides and esters were obtained in moderate to high yields mainly depending on the nucleophile and not on the structure of the 2-iodo[1,2-<em>a</em>]pyridine substrates.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"174 ","pages":"Article 134489"},"PeriodicalIF":2.1,"publicationDate":"2025-01-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143342945","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
Regioselectivity of conjugate addition of secondary amines and thiols to α-substituted enyne aldehydes
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-01-23 DOI: 10.1016/j.tet.2025.134494
Ekaterina A. Verochkina, Victoria G. Fedoseeva, Evgeniy V. Kondrashov, Igor B. Rozentsveig, Ludmila I. Larina, Alexander V. Vashchenko, Nadezhda V. Vchislo
{"title":"Regioselectivity of conjugate addition of secondary amines and thiols to α-substituted enyne aldehydes","authors":"Ekaterina A. Verochkina,&nbsp;Victoria G. Fedoseeva,&nbsp;Evgeniy V. Kondrashov,&nbsp;Igor B. Rozentsveig,&nbsp;Ludmila I. Larina,&nbsp;Alexander V. Vashchenko,&nbsp;Nadezhda V. Vchislo","doi":"10.1016/j.tet.2025.134494","DOIUrl":"10.1016/j.tet.2025.134494","url":null,"abstract":"<div><div>The reaction of 2,5-disubstituted (<em>Z,E</em>)-pent-2-en-4-ynals with secondary amines and thiols has been studied. It is found that only the triple bond is subjected to nucleophilic attack. The interaction of polyunsaturated aldehydes with piperazine leads to a mixture of addition products at the triple bond with the participation of one or both NH-groups. Organogermanium enynal - 2-(butylthio)-5-(triethylgermyl)pent-2-en-4-ynal, gives products of addition at the triple bond with pyrrolidine both with retention and with cleavage of the triethylgermyl group. The regioselectivity of the addition of nucleophiles to α-substituted enyne aldehydes is explained within the framework of DFT methods by comparing both the reactivity indices for competing electrophilic centers (electrophilic Parr functions) and the thermodynamic stability of the resulting products.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"174 ","pages":"Article 134494"},"PeriodicalIF":2.1,"publicationDate":"2025-01-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143343117","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
Copper–amine-complex-catalyzed highly selective oxidative cross-coupling of 2-naphthols: Synthesis of C1-Symmetric BINOLs
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-01-23 DOI: 10.1016/j.tet.2025.134495
Wen-Long Wang, Xiao-Xiong Lv, Fei Chen, Ning Liu, Zhi-Hong Du
{"title":"Copper–amine-complex-catalyzed highly selective oxidative cross-coupling of 2-naphthols: Synthesis of C1-Symmetric BINOLs","authors":"Wen-Long Wang,&nbsp;Xiao-Xiong Lv,&nbsp;Fei Chen,&nbsp;Ning Liu,&nbsp;Zhi-Hong Du","doi":"10.1016/j.tet.2025.134495","DOIUrl":"10.1016/j.tet.2025.134495","url":null,"abstract":"<div><div>An efficient catalytic system based on a copper–amine complex was developed for the oxidative cross-coupling of 3-hydroxy-2-naphthoic acid derivatives and 2-naphthols under mild conditions. The method tolerated a broad substrate scope, and a series of <em>C</em><sub><em>1</em></sub>-symmetrical BINOL derivatives were obtained in excellent yields (up to 93 %). In addition, the model reaction was easily amplified to the gram scale with a relatively consistent yield. The control experiments showed that in this catalytic system, the homocoupling reactions of 2-naphthol derivatives do not take place, and the degree of homocoupling for the 3-hydroxy-2-naphthoic acid derivatives did not exceed 10 %, thereby indicating a high chemical selectivity. At last, a possible mechanism was proposed based on high-resolution mass spectrometry and previous studies.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"174 ","pages":"Article 134495"},"PeriodicalIF":2.1,"publicationDate":"2025-01-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143343118","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
Visible‐light‐mediated synthesis of 2H-indazoles from (2-bromo-benzylidene)-phenyl-amine derivatives by the Ullmann Goldberg reaction
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-01-23 DOI: 10.1016/j.tet.2025.134486
Ali Akbari, Danial Zand Hosein shahi, Ali Rahimabadi
{"title":"Visible‐light‐mediated synthesis of 2H-indazoles from (2-bromo-benzylidene)-phenyl-amine derivatives by the Ullmann Goldberg reaction","authors":"Ali Akbari,&nbsp;Danial Zand Hosein shahi,&nbsp;Ali Rahimabadi","doi":"10.1016/j.tet.2025.134486","DOIUrl":"10.1016/j.tet.2025.134486","url":null,"abstract":"<div><div>Copper oxide-Titanium dioxide nanocomposites (CuO/TiO<sub>2</sub> NC) is an efficient photocatalyst for the synthesis of 2<em>H</em>-indazoles derivatives through intermolecular C–N bond (Ullmann Goldberg reaction) and intramolecular N–N bond formation. The CuO/TiO<sub>2</sub> NC is a stable photocatalyst and can be reused multiple times without losing its catalytic properties. High yields of product, environmentally friendly, cost-effective method, and easy workup are advantages of the present method. All synthesized compounds were characterized by NMR spectroscopy.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"174 ","pages":"Article 134486"},"PeriodicalIF":2.1,"publicationDate":"2025-01-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143343119","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
Photo-driven aerobic C(sp3)-H oxidation by organic photocatalysts: A recent review
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-01-23 DOI: 10.1016/j.tet.2025.134496
Mianran Chao , Qin Zhang , Ge Jin , Guiwen Guo , Xuan Cheng , Duyi Shen
{"title":"Photo-driven aerobic C(sp3)-H oxidation by organic photocatalysts: A recent review","authors":"Mianran Chao ,&nbsp;Qin Zhang ,&nbsp;Ge Jin ,&nbsp;Guiwen Guo ,&nbsp;Xuan Cheng ,&nbsp;Duyi Shen","doi":"10.1016/j.tet.2025.134496","DOIUrl":"10.1016/j.tet.2025.134496","url":null,"abstract":"<div><div>The direct oxidation and oxygenation of C(sp<sup><strong>3</strong></sup>)-H bonds has profound significance in synthetic chemistry for straightforwardly installing valuable C-O and C<img>O bonds on bulk chemicals without pre-functionalization step. However, the development of highly efficient and selective catalytic methods under mild reactions remains to be a challenge due to the large bond dissociation energy as well as the competition oxidation among intramolecular C(sp<sup><strong>3</strong></sup>)-H bonds. Light-induced C(sp<sup><strong>3</strong></sup>)-H oxidation by organic photocatalysts should be a powerful tool since strong oxidative species could be achieved at the excited states at ambient temperature. In addition, this process will become more environmentally friendly when molecular oxygen, with high atom economy and eco-compatibility, is used as the terminal oxidant. During the past decade, the combination of photo irradiation and molecular oxygen or even air under metal-free condition, as a promising catalytic approach, has received increasing attention and become the method of choice for the activation of C(sp<sup><strong>3</strong></sup>)-H bonds. This review introduced briefly the pioneering works and listed detailed updates of the methodology development, synthetic applications especially in the late-stage modification of drugs or natural products, and mechanism studies on photo-promoted aerobic C(sp<sup><strong>3</strong></sup>)-H oxidation/oxygenation by organic catalysts from 2020 to 2024. And this review is divided by the type of organic photocatalysts used in the C-H activation reactions. The production of oxygenated compounds, such as ketone, aldehyde, alcohol, hydroperoxide, and lactone has been accomplished by various of organic photocatalysts alone or the synergistic catalysis with a co-catalyst as the indirect hydrogen atom abstractor. The reaction scope, limitation, challenge, and future opportunities in this field have been discussed as well.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"174 ","pages":"Article 134496"},"PeriodicalIF":2.1,"publicationDate":"2025-01-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143342871","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
BF3-catalyzed nucleophilic addition reaction of 1,2-diaminobenzenes with α-ketoesters: Access to cyclic α,α-disubstituted α-amino acid derivatives
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-01-23 DOI: 10.1016/j.tet.2025.134487
Zhen Yao , Ji Yang , Rong Huang , Chang Liu , Jing Guan , Ying Zhou , Xiongwei Liu , Bing Lin , Lijin Xu
{"title":"BF3-catalyzed nucleophilic addition reaction of 1,2-diaminobenzenes with α-ketoesters: Access to cyclic α,α-disubstituted α-amino acid derivatives","authors":"Zhen Yao ,&nbsp;Ji Yang ,&nbsp;Rong Huang ,&nbsp;Chang Liu ,&nbsp;Jing Guan ,&nbsp;Ying Zhou ,&nbsp;Xiongwei Liu ,&nbsp;Bing Lin ,&nbsp;Lijin Xu","doi":"10.1016/j.tet.2025.134487","DOIUrl":"10.1016/j.tet.2025.134487","url":null,"abstract":"<div><div>A metal-free nucleophilic addition reaction of readily available 1,2-diaminobenzenes with α-ketoesters for synthesis of heterocyclic α,α-disubstituted-α-amino acids at room temperature under BF<sub>3</sub>·Et<sub>2</sub>O catalysis has been accomplished. This transformation occurs smoothly under mild conditions, providing easy access to various heterocyclic α,α-disubstituted-α-amino acids in 54–93 % yields with ample substrate scope, high compatibility of functional groups and easy scale-up. Choosing BF<sub>3</sub>·Et<sub>2</sub>O as Lewis acid is crucial for the success of this transformation.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"174 ","pages":"Article 134487"},"PeriodicalIF":2.1,"publicationDate":"2025-01-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143343122","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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