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Reactions of Benzyl Phosphine Oxide/Sulfide with (COCl)2: Synthesis of Novel Acyl Chloride-Substituted Chlorophosphonium Ylides 苄基氧化膦/硫醚与 (COCl)2 的反应：合成新型酰基氯取代的氯膦酰化物
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-24 DOI: 10.1021/acs.joc.4c01720
Peng Zhao, Mengting Liu, Ying Li, Lili Wang, Zheng Duan
{"title":"Reactions of Benzyl Phosphine Oxide/Sulfide with (COCl)2: Synthesis of Novel Acyl Chloride-Substituted Chlorophosphonium Ylides","authors":"Peng Zhao, Mengting Liu, Ying Li, Lili Wang, Zheng Duan","doi":"10.1021/acs.joc.4c01720","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01720","url":null,"abstract":"New reactions of benzyl phosphine oxide/sulfide with oxalyl chloride are presented. The resulting reactive intermediates, acyl chloride-substituted chlorophosphonium ylides, are capable of undergoing esterification and Friedel–Crafts acylation reactions, ultimately yielding either methyl 2-(2-bromophenyl)-2-(diphenylphosphoryl)acetate or β-carbonyl-diarylphosphine oxide derivatives. Additionally, when an alkynyl group is contained in the acyl chloride-substituted chlorophosphonium ylide, intramolecular cyclization occurs, leading to the formation of a pair of <i>trans-</i> and <i>cis-</i>dichlorophosphonyl benzofulvene isomers. The generation process of acyl chloride-substituted chlorophosphonium ylide was carefully monitored by using <sup>31</sup>P{<sup>1</sup>H} NMR spectroscopy, and a plausible reaction mechanism was proposed.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-09-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142314037","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
Stereo- and Regioselective Installation of Vinyl Sulfonyl Fluoride onto Indoles without Transition-Metal Catalyst. 在无过渡金属催化剂的情况下，将乙烯基磺酰氟立体和区域选择性地安装到吲哚上。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-24 DOI: 10.1021/acs.joc.4c01689
Shu-Zhen Zheng, Eman Fayad, Najla A Alshaye, Hua-Li Qin
{"title":"Stereo- and Regioselective Installation of Vinyl Sulfonyl Fluoride onto Indoles without Transition-Metal Catalyst.","authors":"Shu-Zhen Zheng, Eman Fayad, Najla A Alshaye, Hua-Li Qin","doi":"10.1021/acs.joc.4c01689","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01689","url":null,"abstract":"<p><p>Herein, we developed a practical method for synthesizing a class of novel and highly valuable indolyl vinyl sulfonyl fluorides. This protocol has carved out a path for constructing a broad range of vinyl sulfonyl fluorinated indoles with exclusive stereo- and regioselectivity through the Friedel-Crafts/elimination reaction without any transition-metal catalyst. This transformation features mild conditions, high efficiency, excellent selectivity, and rich substrate compatibility, highlighting its significant value in medicinal chemistry and many related disciplines.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-09-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142306627","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
Total Synthesis of Chalaniline A: An Aminofulvene Fused Chromone from Vorinostat-Treated Fungus Chalara sp. 6661. Chalaniline A 的全合成：来自 Vorinostat 处理过的真菌 Chalara sp.
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-23 DOI: 10.1021/acs.joc.4c01855
Pannaporn Prapapongpan, Veerapattha Vanthiya, Oh-Seok Kwon, Lev N Zakharov, Sandra Loesgen, Paul R Blakemore
{"title":"Total Synthesis of Chalaniline A: An Aminofulvene Fused Chromone from Vorinostat-Treated Fungus <i>Chalara</i> sp. 6661.","authors":"Pannaporn Prapapongpan, Veerapattha Vanthiya, Oh-Seok Kwon, Lev N Zakharov, Sandra Loesgen, Paul R Blakemore","doi":"10.1021/acs.joc.4c01855","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01855","url":null,"abstract":"<p><p>Chalaniline A, an aminofulveno[1,2-<i>b</i>]chromone derivative previously isolated from a vorinostat-treated ascomycete <i>Chalara</i> sp., was prepared in nine steps from orcinol (3,5-dihydroxytoluene). In a key transformation, the tricyclic ring system of the target was generated by a pyrrolidine-catalyzed double annulation between α-(methylsulfinyl)-2,6-dihydroxy-4-methylacetophenone and the ketaldoester, methyl 2,5-dioxopentanoate. The resulting tertiary alcohol (coniochaetone H) was further converted to chalaniline A by operations including dehydration (to yield a hydroxyfulvene), Vilsmeier reaction, and enamine exchange.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-09-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142277370","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
Theoretical Study on the Mechanism of Ru(II)-Catalyzed Intermolecular [3 + 2] Annulation between o-Toluic Acid and 3,5-Bis(trifluoromethyl)benzaldehyde: Octahedral vs Trigonal Bipyramidal Ru(II)- 催化邻甲基苯甲酸与 3,5-双三氟甲基苯甲醛分子间[3 + 2]嵌合的机理理论研究：八面体与三叉双锥体
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-23 DOI: 10.1021/acs.joc.4c01461
Dan-Yang Liu, De-Cai Fang
{"title":"Theoretical Study on the Mechanism of Ru(II)-Catalyzed Intermolecular [3 + 2] Annulation between o-Toluic Acid and 3,5-Bis(trifluoromethyl)benzaldehyde: Octahedral vs Trigonal Bipyramidal","authors":"Dan-Yang Liu, De-Cai Fang","doi":"10.1021/acs.joc.4c01461","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01461","url":null,"abstract":"Density functional theory was utilized to investigate the mechanism of Ru(II)-catalyzed aromatic C–H activation and addition of aromatic aldehydes. The proposed catalytic cycle consists of C–H bond activation, aldehyde carbonyl insertion for C–C coupling, lactonization for the formation of the final product, product separation, and catalyst recovery. Our calculations suggest that Ru(OAc)<sub>2</sub>(PCy<sub>3</sub>) (referred to as <b>CAT</b>) is the most favorable active catalyst, facilitating the C–H bond activation to form a five-membered ring cycloruthenium intermediate (<b>INT2</b>). Subsequently, the aromatic aldehyde reactant <b>2a</b> enters the Ru coordination sphere, accelerating the C–C coupling and lactonization for the formation of the final product. The involvement of acetate assists in the final product separation, while <b>INT1</b> re-enters the Ru coordination sphere to initiate a new catalytic cycle. Utilizing the energetic span model, the apparent activation free energy barrier was computed to be 34.3 kcal mol<sup>–1</sup> at 443 K. Furthermore, exploration of the reaction mechanism in the absence of phosphine ligands identified Ru(OAc)<sub>2</sub>(<i>p</i>-cymene) as the most favorable active catalyst. The derived apparent activation free energy barrier offers a comprehensive explanation for the experimentally observed yields. Additionally, we have examined the disparities between the octahedral and trigonal bipyramidal structures of the catalysts concerning their effects on the reaction mechanisms and apparent activation free energy barriers.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-09-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142306298","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
The GaCl3-Catalyzed Knoevenagel Condensation To Achieve Acceptor-Donor-Acceptor Small-Molecule Acceptors: A DFT Mechanistic Study. GaCl3 催化 Knoevenagel 缩合实现受体-供体-受体小分子受体：DFT 机制研究。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-23 DOI: 10.1021/acs.joc.4c01806
Xiaofan Shi, Yaqi Zhao, Ying Zhou, Zhewei Li, Yanhui Tang, Hongyuan Fu, Yangqiu Liu, Zhi-Guo Zhang, Min Pu, Ming Lei
{"title":"The GaCl<sub>3</sub>-Catalyzed Knoevenagel Condensation To Achieve Acceptor-Donor-Acceptor Small-Molecule Acceptors: A DFT Mechanistic Study.","authors":"Xiaofan Shi, Yaqi Zhao, Ying Zhou, Zhewei Li, Yanhui Tang, Hongyuan Fu, Yangqiu Liu, Zhi-Guo Zhang, Min Pu, Ming Lei","doi":"10.1021/acs.joc.4c01806","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01806","url":null,"abstract":"<p><p>Herein, the reaction mechanism for the GaCl<sub>3</sub>-catalyzed Knoevenagel condensation of 2-formylindacenodithieno[3,2-<i>b</i>]thiophene (ITIC-CHO) and active methylene compound 1,1-dicyanomethylene-3-indanone (IC) to synthesize ITIC in the presence of acetic anhydride was investigated using the density functional theory (DFT) method. The calculated results indicate that this reaction follows a bimolecular GaCl<sub>3</sub> catalytic mechanism. The free energy span for the monomolecular GaCl<sub>3</sub> catalytic mechanism is the highest (31.8 kcal/mol), followed by the trimolecular GaCl<sub>3</sub> catalytic mechanism (26.4 kcal/mol) and the bimolecular GaCl<sub>3</sub> catalytic mechanism (26.3 kcal/mol). The trimolecular GaCl<sub>3</sub> path and bimolecular GaCl<sub>3</sub> path are competitive, but the former path is limited by the concentration of GaCl<sub>3</sub>. The inclusion of GaCl<sub>3</sub> could stabilize the transition states of C-H activation. Compared to the GaCl<sub>3</sub>-catalyzed Knoevenagel condensation, that catalyzed by pyridine is not advantageous, owning a high energy span of 31.7 kcal/mol. These agree well with experimental results. This work could provide a novel theoretical understanding of the Knoevenagel condensation, which could inspire the development of a synthesis strategy for electron acceptor materials.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-09-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142277369","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 and Stabilization of Highly Reactive Haloacetylium Ions. 高活性卤乙酰离子的合成与稳定。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-23 DOI: 10.1021/acs.joc.4c01783
Sebastian Steiner, Christoph Jessen, Alexander Nitzer, Valentin Bockmair, Andreas J Kornath
{"title":"Synthesis and Stabilization of Highly Reactive Haloacetylium Ions.","authors":"Sebastian Steiner, Christoph Jessen, Alexander Nitzer, Valentin Bockmair, Andreas J Kornath","doi":"10.1021/acs.joc.4c01783","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01783","url":null,"abstract":"<p><p>The reactions of selected haloacetyl fluorides with the strong Lewis acids AsF<sub>5</sub> and SbF<sub>5</sub> were investigated in the aprotic solvent SO<sub>2</sub>ClF. Depending on the stoichiometric ratio of AsF<sub>5</sub> or SbF<sub>5</sub> and the haloacetyl fluorides, either <i>O</i>-coordinated adducts or the respective haloacetylium ions were isolated as solids. The compounds were characterized by low-temperature vibrational spectroscopy and single-crystal X-ray diffraction. [CClH<sub>2</sub>CO][Sb<sub>2</sub>F<sub>11</sub>] and [CH<sub>2</sub>FCO][Sb<sub>2</sub>F<sub>11</sub>] crystallize in the monoclinic space group <i>P</i>2<sub>1</sub> with two formula units per unit cell. The reactivity of the haloacetyl fluorides under Lewis acidic conditions is discussed based on quantum chemical calculations of fluoride ion affinities on the BP/def2SVPP level of theory. The haloacetylium ions are stabilized in the solid-state phase by intermolecular C···F contacts and electron donation of the fluorine ligands of the anions as well as intramolecular hyperconjugation.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-09-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142277368","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
Indolizinylalanine Regioisomers: Tryptophan Isosteres with Bathochromic Fluorescence Emission. 吲哚嗪基丙氨酸 Regioisomers：具有浴色荧光发射的色氨酸异构体。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-22 DOI: 10.1021/acs.joc.4c01203
Gabriella I D Cooper, Ishika Saha, Jacob Newman, Ruthy H Shin, Patrick G Harran
{"title":"Indolizinylalanine Regioisomers: Tryptophan Isosteres with Bathochromic Fluorescence Emission.","authors":"Gabriella I D Cooper, Ishika Saha, Jacob Newman, Ruthy H Shin, Patrick G Harran","doi":"10.1021/acs.joc.4c01203","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01203","url":null,"abstract":"<p><p>We have developed a high yielding synthesis of indolizine and directly elaborated the molecule into three optically active indolizinylalanine regioisomers. The protocols exploit metal catalyzed coupling of indolizinyl-halides with organozinc reagents derived from carbamoylated iodoalanine esters. The scalable protocols provide products in a form amenable to solid-phase peptide synthesis (SPPS). When incorporated into peptides, the indolizine heterocycle is more basic and markedly less nucleophilic than tryptophan. Its protonated vinylpyridinium form is deeply colored in solution while the neutral heterocycle is highly fluorescent. The fluorescence quantum yield of indolizine exceeds that of indole and aza-indoles in water, suggesting that indolizinylalanines could be powerful optical probes of protein structure and dynamics, functioning as true tryptophan isosteres.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-09-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142277365","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
Reaction of Isatin and 2-Chloropyridinium Salt: An Efficient and Diastereoselective Synthesis of α,β-Unsaturated Oxindoles. 靛红和 2-氯吡啶鎓盐的反应：α、β-不饱和羰基吲哚的高效和非对映选择性合成。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-22 DOI: 10.1021/acs.joc.4c01069
Kaveh Imani, Hamideh Shirazi, Golnaz Golchin, Ayoob Bazgir
{"title":"Reaction of Isatin and 2-Chloropyridinium Salt: An Efficient and Diastereoselective Synthesis of α,β-Unsaturated Oxindoles.","authors":"Kaveh Imani, Hamideh Shirazi, Golnaz Golchin, Ayoob Bazgir","doi":"10.1021/acs.joc.4c01069","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01069","url":null,"abstract":"<p><p>A new, mild, and diastereoselective method has been developed for the synthesis of β-pyridone-α,β-unsaturated oxindoles by the reaction of isatins and 2-chloropyridinium salts in EtOH at room temperature for 5 min. This method operates under mild reaction conditions, providing the product with a good yield and diastereoselectivity, and it exhibits excellent tolerance toward various functional groups. The predominant isomer is the <i>Z</i> isomer, which can convert to the <i>E</i> isomer in the presence of NaN<sub>3</sub>.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-09-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142277366","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
Strategies and Tactics for Site Specific Deuterium Incorporation at Each Available Carbon Atom of α-Pinene. 在α-蒎烯的每个可用碳原子上进行特定位点氘结合的策略和战术。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-22 DOI: 10.1021/acs.joc.4c01702
Jingyi Luo, Mary Alice Upshur, Marvin Vega, Nicolle A Doering, Jonathan Varelas, Zhouyang Ren, Franz M Geiger, Richmond Sarpong, Regan J Thomson
{"title":"Strategies and Tactics for Site Specific Deuterium Incorporation at Each Available Carbon Atom of α-Pinene.","authors":"Jingyi Luo, Mary Alice Upshur, Marvin Vega, Nicolle A Doering, Jonathan Varelas, Zhouyang Ren, Franz M Geiger, Richmond Sarpong, Regan J Thomson","doi":"10.1021/acs.joc.4c01702","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01702","url":null,"abstract":"<p><p>The development of several unique strategies and tactics for the synthesis of α-pinene isotopologues that has culminated in access to all eight possible isomers with deuterium incorporated selectively at each available carbon atom is described. Access to this library of isotopologues provides new tools to more fully investigate the atmospheric autoxidation of α-pinene, a complex process that plays a major role in the formation of secondary organic aerosol in the Earth's atmosphere.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-09-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142277367","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
Intramolecular Silanoxy-Michael Reactions with Pendant Nitroalkenes: Racemic and Enantioselective 分子内硅烷氧-迈克尔反应与附硝基烯：外消旋和对映体选择性
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-21 DOI: 10.1021/acs.joc.4c01625
Harshit Joshi, Shyam Sathyamoorthi
{"title":"Intramolecular Silanoxy-Michael Reactions with Pendant Nitroalkenes: Racemic and Enantioselective","authors":"Harshit Joshi, Shyam Sathyamoorthi","doi":"10.1021/acs.joc.4c01625","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01625","url":null,"abstract":"We present the first racemic and scalemic examples of di-<i>tert</i>-butyl silanoxy-Michael additions. Our operationally simple protocol is selective for nitro-olefins and simply involves stirring the substrate with an appropriate hydrogen-bond donor catalyst without any special precautions to exclude air or moisture. For each substrate examined, we have developed complementary protocols that optimize yield and enantioselectivity. Our reactions scale well, and the products are valuable intermediates for further transformations, including for the preparation of enantioenriched vicinal amino alcohols.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-09-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142273615","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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