Journal of Organic Chemistry最新文献

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Palladium-Catalyzed Autotandem Ring-Opening of Cyclopropanols with Gem-Dibromoolefins for the Synthesis of β-Pyrrolo[1,2-a]quinolinyl Ketones
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-12 DOI: 10.1021/acs.joc.4c02061
Ping-Xin Zhou, Xue-Yan Du, Yang Liu, Si-Hui Qiu, Qiang Wang, Ying-Ying Kong, Yong-Min Liang
{"title":"Palladium-Catalyzed Autotandem Ring-Opening of Cyclopropanols with Gem-Dibromoolefins for the Synthesis of β-Pyrrolo[1,2-a]quinolinyl Ketones","authors":"Ping-Xin Zhou, Xue-Yan Du, Yang Liu, Si-Hui Qiu, Qiang Wang, Ying-Ying Kong, Yong-Min Liang","doi":"10.1021/acs.joc.4c02061","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02061","url":null,"abstract":"Herein, the palladium-catalyzed autotandem reaction of cyclopropyl alcohols with gem-dibromoolefins is described. This reaction system involves two distinct mechanistic processes, both efficiently catalyzed by the same palladium catalyst. This approach accommodates a wide substrate scope using readily available starting materials, offering a new and efficient method for synthesizing a series of β-pyrrolo[1,2-<i>a</i>]quinolinyl ketones.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"41 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142810034","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Controllable Synthesis of Benzo[b]furo[2,3-d]azepines or Furo[3,2-b]indoles via Intermolecular Oxidative Annulation of 2-(Furan-2-yl)anilines and Propargyl Carbonates versus Intramolecular C–H Amination Reactions
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-12 DOI: 10.1021/acs.joc.4c02293
Rong Ma, Yujie Qu, Pengcheng Guan, Minghui Liu, Yu Han, Feng Feng, Chengyu Wang
{"title":"Controllable Synthesis of Benzo[b]furo[2,3-d]azepines or Furo[3,2-b]indoles via Intermolecular Oxidative Annulation of 2-(Furan-2-yl)anilines and Propargyl Carbonates versus Intramolecular C–H Amination Reactions","authors":"Rong Ma, Yujie Qu, Pengcheng Guan, Minghui Liu, Yu Han, Feng Feng, Chengyu Wang","doi":"10.1021/acs.joc.4c02293","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02293","url":null,"abstract":"Two novel Pd-catalyzed protocols for the controllable synthesis of benzo[<i>b</i>]furo[2,3-<i>d</i>]azepines and furo[3,2-<i>b</i>]indoles have been developed by intermolecular oxidative annulation of 2-(furan-2-yl)anilines and propargyl carbonates versus intramolecular C–H amination reactions. These two protocols feature great scalability, functional group tolerance, and relatively mild reaction conditions. Notably, the robust methodologies could also provide valuable opportunities for assembling azepine-fused benzothiophene, indole-fused benzothiophene, and indole-fused benzimidazole, which may have potential applications in the synthesis of related pharmaceuticals or polymeric materials.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"14 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142810035","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Nondirected Ortho C–H Arylation for One-Pot Synthesis of Biaryl Scaffolds via In Situ Generated Mixed Acetal
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-12 DOI: 10.1021/acs.joc.4c01984
Aparna Tyagi, Himanshu Gautam, Khyati Tripathi, Chinmoy K. Hazra
{"title":"Nondirected Ortho C–H Arylation for One-Pot Synthesis of Biaryl Scaffolds via In Situ Generated Mixed Acetal","authors":"Aparna Tyagi, Himanshu Gautam, Khyati Tripathi, Chinmoy K. Hazra","doi":"10.1021/acs.joc.4c01984","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01984","url":null,"abstract":"Herein, we introduce a mild and efficient method for synthesizing aniline biaryls and unsymmetrical phenol biaryls through iodine-catalyzed coupling of quinone imine ketals (QIKs)/quinonemonoacetals (QMAs) and <i>β</i>-naphthols. This approach allows for the unusual formation of ortho-substituted anilines and phenols, valuable in pharmaceuticals and advanced materials but typically difficult to produce. Our method achieves high <i>ortho</i>-selectivity without needing transition metals or external/internal templates. The process involves a [3,3] sigmatropic rearrangement of the <i>in situ</i> generated mixed acetal, which is the key intermediate. Notable features include scalability, broad functional group tolerance, and late-stage derivatization of natural products using a cost-effective, air-tolerant catalytic system, eliminating the need for hazardous catalysts.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"16 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142810032","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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 Hat Trick: 1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD)-Catalyzed Synthesis of Cyclic Imides via an Amidation–Cyclization–Elimination Cascade
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-12 DOI: 10.1021/acs.joc.4c02649
Chunling Blue Lan, Karine Auclair
{"title":"Organocatalytic Hat Trick: 1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD)-Catalyzed Synthesis of Cyclic Imides via an Amidation–Cyclization–Elimination Cascade","authors":"Chunling Blue Lan, Karine Auclair","doi":"10.1021/acs.joc.4c02649","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02649","url":null,"abstract":"1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD) was used for the synthesis of cyclic imides via an amidation–cyclization–elimination cascade. This organocatalytic transformation features both the traditional reactivity of TBD and its unprecedented C–C bond cleavage capability, allowing rapid and efficient access to cyclic imides. This method is compatible with the late-stage functionalization of complex molecules and the synthesis of bioactive molecules. Both experimental and computational approaches were employed to gain a better understanding of the reaction mechanism.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"40 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142810036","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Silver Oxide Promoted Synthesis of Alpha O-GalNAc Containing Glyco-Amino Acids: Synthesis of Core 2 Containing Glyco-Amino Acids for Solid Phase Synthesis of Glycopeptides
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-12 DOI: 10.1021/acs.joc.4c01572
Ousman Boye, Lisa Nicholson, Anna Marstall, Brooke Van Engen, Marika Van Slageren, Noah Mulder, Mostafa Ali Eldeen, Abe Hall, Anjaneyulu Putta, Sandeep K. Misra, Joshua S. Sharp, Hailiang Joshua Zhu
{"title":"Silver Oxide Promoted Synthesis of Alpha O-GalNAc Containing Glyco-Amino Acids: Synthesis of Core 2 Containing Glyco-Amino Acids for Solid Phase Synthesis of Glycopeptides","authors":"Ousman Boye, Lisa Nicholson, Anna Marstall, Brooke Van Engen, Marika Van Slageren, Noah Mulder, Mostafa Ali Eldeen, Abe Hall, Anjaneyulu Putta, Sandeep K. Misra, Joshua S. Sharp, Hailiang Joshua Zhu","doi":"10.1021/acs.joc.4c01572","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01572","url":null,"abstract":"<i>O</i>-GalNAc glycans on glycoproteins with eight different core structures sharing a common α-glycosidic linkage (<i>O</i>-GalNAc-α-Ser/Thr) are critical in various physiological and pathological processes. Among the eight <i>O</i>-GalNAc glycan cores, core 2 characterized by a GlcNAcβ1–6(Galβ1–3)GalNAc structural motif plays a significant role in regulating diverse biological processes, such as immune response modulation, adhesive properties of selectins, and gastrointestinal tract protection. However, the large-quantity synthesis of core 2 containing glyco-amino acids for downstream solid-phase peptide synthesis is challenging. In this work, we successfully employed a silver oxide for coupling a 2-azido-galactosyl chloride donor with two acceptors, Fmoc-Ser/Thr-O<sup>t</sup>Bu, respectively, for the large-scale synthesis of the two important intermediates, α-GalN<sub>3</sub>–Fmoc-Ser/Thr-O<sup>t</sup>Bu, which can be further utilized for the large-scale synthesis of core 2 containing glyco-amino acids. The two intermediates, α-GalN<sub>3</sub>–Fmoc-Ser/Thr-O<sup>t</sup>Bu, were utilized for synthesizing core 2 containing Fmoc-Ser/Thr-COOH. The synthesis of core 2 containing Fmoc-Ser-COOH was achieved on a 1.95 g scale, while the synthesis of core 2 containing Fmoc-Thr-COOH was achieved on a 0.38 g scale. Additionally, the synthesis of the 2-azido-galactosyl chloride donor was optimized into a three-step process with only one column chromatography purification. Finally, core 2 containing Fmoc-Ser/Thr-COOH were applied for the synthesis of glycosylated CCR1 and CCR5 N-terminal peptides.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"12 4 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142810031","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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, Protonation and Aromatic Characteristics of a Series of 1,10-Phenanthroline-Fused Porphyrinoids
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-12 DOI: 10.1021/acs.joc.4c01511
Victoria C. Ujah, Deyaa I. AbuSalim, Timothy D. Lash
{"title":"Synthesis, Protonation and Aromatic Characteristics of a Series of 1,10-Phenanthroline-Fused Porphyrinoids","authors":"Victoria C. Ujah, Deyaa I. AbuSalim, Timothy D. Lash","doi":"10.1021/acs.joc.4c01511","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01511","url":null,"abstract":"A series of porphyrin analogues with fused 1,10-phenanthroline units were synthesized. The proton NMR spectra for phenanthroline-fused heteroporphyrins showed significantly upfield shifted <i>meso</i>-proton resonances compared to related porphyrinoid systems and the peaks corresponding to alkyl substituents directly attached to these macrocycles were also observed further upfield. These results indicate that the presence of the phenanthroline unit leads to reduced diatropicity, but the internal NH resonance was also further upfield, a result that is inconsistent with this interpretation. A phenanthrene-fused carbaporphyrin gave an unexpectedly upfield singlet for the internal C–H at nearly −9 ppm, while the NH protons appeared at −6.8 ppm. These unusual chemical shifts again imply enhanced diatropicity but the reduced downfield shifts for the external protons indicates that the aromatic ring current has been significantly reduced. Similar results were obtained for phenanthroline-fused oxybenzi- and oxypyriporphyrins. Detailed analyses of the spectroscopic properties for these systems are reported and protonation studies were conducted. The conjugation pathways and aromatic properties were computationally analyzed using nucleus independent chemical shifts (NICS) and anisotropy of induced current density plots.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"4 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142810030","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Bifunctional Sodium Dithionite Promoted Radical-Polar Crossover Cyclization: Diversified Synthesis of Functionalized Cyclic Sultines
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-11 DOI: 10.1021/acs.joc.4c02606
Cheng-Jing Li, Meng-Yu Liu, Zhong-Lin Wei, Wei-Wei Liao
{"title":"Bifunctional Sodium Dithionite Promoted Radical-Polar Crossover Cyclization: Diversified Synthesis of Functionalized Cyclic Sultines","authors":"Cheng-Jing Li, Meng-Yu Liu, Zhong-Lin Wei, Wei-Wei Liao","doi":"10.1021/acs.joc.4c02606","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02606","url":null,"abstract":"A catalyst-free reductive radical-polar crossover cyclization with alkenes and sodium dithionite to construct densely functionalized cyclic sultines was described. The key to the success of this practical protocol relies not only on a bifunctional role of sodium dithionite, that is, serving as radical initiator and SO<sub>2</sub> source, but also on the diversified conversions (RPCC/SO<sub>2</sub> insertion/S<sub>N</sub>2 cyclization and RPCC/SO<sub>2</sub> insertion/1,4-addition cyclization processes), which enabled efficient construction of target compounds with the high efficiency and atom- and step-economy under mild conditions.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"14 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142810038","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Environmentally Stable Reversible Cavitand Molecular Switches Based on the Excimer of Perylene
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-11 DOI: 10.1021/acs.joc.4c01196
Zhi Yu, Yixing He, Pan Liao, Selina X. Yao, Yuping Zhao, Wenjie Liang, Weiying Lin, Martin Saunders, Hai Xu
{"title":"Environmentally Stable Reversible Cavitand Molecular Switches Based on the Excimer of Perylene","authors":"Zhi Yu, Yixing He, Pan Liao, Selina X. Yao, Yuping Zhao, Wenjie Liang, Weiying Lin, Martin Saunders, Hai Xu","doi":"10.1021/acs.joc.4c01196","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01196","url":null,"abstract":"Environmentally stable novel flexible bisperylene resorcin[4]arene molecular switch cavitand B and the corresponding rigid cavitand A were synthesized and a single crystal was obtained. Spectroscopic analysis revealed the formation of an excimer of perylene within the cavitand. The presence of flexible chains in cavitand B confers a high degree of environmental stability, rendering its fluorescence unaffected by external factors such as pH and temperature variations. In contrast, the rigid cavitand A exhibits heightened sensitivity to changes in environmental conditions.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"7 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142804998","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Anion–Cation–Anion Ion Triplet Characterization by Computation and Photoelectron Spectroscopy
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-11 DOI: 10.1021/acs.joc.4c02392
Wenjin Cao, Xue-Bin Wang, Steven R. Kass
{"title":"Anion–Cation–Anion Ion Triplet Characterization by Computation and Photoelectron Spectroscopy","authors":"Wenjin Cao, Xue-Bin Wang, Steven R. Kass","doi":"10.1021/acs.joc.4c02392","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02392","url":null,"abstract":"Ion triplets of the chloride salts of two commonly used weakly coordinating cations are reported (i.e., Cl<sup>–</sup>·NMe<sub>4</sub><sup>+</sup>Cl<sup>–</sup> (<b>1</b><sup><b>–</b></sup>) and Cl<sup>–</sup>·PPh<sub>4</sub><sup>+</sup>Cl<sup>–</sup> (<b>2</b><sup><b>–</b></sup>)). Negative ion photoelectron spectra at 20 K afford vertical and adiabatic detachment energies of 5.18 and 5.00 eV (<b>1</b><sup><b>–</b></sup>) and 5.03 and 4.70 eV (<b>2</b><sup><b>–</b></sup>), respectively. These results are well reproduced by coupled cluster calculations with single, double, and perturbative triple excitations (CCSD(T)) whereas M06-2X is systematically too small by ∼0.3 eV (i.e., 7 kcal mol<sup>–1</sup>). The structures of both <b>1</b><sup><b>–</b></sup> and <b>2</b><sup><b>–</b></sup> have five or six C–H···Cl<sup>–</sup> interactions that stabilize these cluster anions by 32 (<b>1</b><sup><b>–</b></sup>) and 27 (<b>2</b><sup><b>–</b></sup>) kcal mol<sup>–1</sup> as given by their chloride dissociation enthalpies. These values drop to 7.4 and 3.8 kcal mol<sup>–1</sup> in dichloromethane based up conductor-like polarizable continuum model calculations and suggest that X<sup>–</sup>·M<sup>+</sup>X<sup>–</sup> ion triplets with a weakly coordinating cation maybe the reactive form of salts under some conditions.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"77 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142805038","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Palladium-Catalyzed Dual C–H Arylation/Cyclization Reaction of Iodoferrocenes with ortho-Bromobenzamides for the Construction of Arylated Isoquinolone-Fused Ferrocenes
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-11 DOI: 10.1021/acs.joc.4c02128
Zhiyong Li, Jingyu Li, Jingwen Fan, Yuhao Ding, Hailin Guo, Guolin Cheng
{"title":"Palladium-Catalyzed Dual C–H Arylation/Cyclization Reaction of Iodoferrocenes with ortho-Bromobenzamides for the Construction of Arylated Isoquinolone-Fused Ferrocenes","authors":"Zhiyong Li, Jingyu Li, Jingwen Fan, Yuhao Ding, Hailin Guo, Guolin Cheng","doi":"10.1021/acs.joc.4c02128","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02128","url":null,"abstract":"We reported a palladium/norbornene-catalyzed dual intermolecular C–H arylation/intramolecular cyclization reaction of iodoferrocenes with <i>ortho</i>-bromobenzamides, enabling the formation of arylated isoquinolone-fused ferrocenes in a straightforward and effective manner. This method has a broad substrate scope and good functional group compatibility, while the gram-scale reaction demonstrates the practicality of this method.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"1 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142810037","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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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