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Diaryliodonium Salt‐Mediated Radical Transformation of Indoles with Alcohols for the Synthesis of Unsymmetrical Bis(indolyl)methanes 二迭碘鎓盐介导的吲哚与醇的自由基转化，用于合成不对称的双（吲哚基）甲烷
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-19 DOI: 10.1002/adsc.202400827
Hongzhen Wang , Haohao Jiang , Shuizhen Lin , Shuoshuo Zhang , Xiaolei Huang
{"title":"Diaryliodonium Salt‐Mediated Radical Transformation of Indoles with Alcohols for the Synthesis of Unsymmetrical Bis(indolyl)methanes","authors":"Hongzhen Wang ,&nbsp;Haohao Jiang ,&nbsp;Shuizhen Lin ,&nbsp;Shuoshuo Zhang ,&nbsp;Xiaolei Huang","doi":"10.1002/adsc.202400827","DOIUrl":"10.1002/adsc.202400827","url":null,"abstract":"<div><div>A method for the synthesis of unsymmetrical bis(indolyl)methanes (BIMs) using simple indoles and readily available alcohols as the coupling partners under both heat and 390–400 nm light conditions was developed. Detailed research of the mechanism demonstrated that the diaryliodonium salt‐mediated transformation undergoes a nucleophilic hydroxymethyl radical formation process. Moreover, the diaryliodonium salt‐mediated method is also applicable for synthesizing symmetrical BIMs.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"366 22","pages":"Pages 4765-4771"},"PeriodicalIF":4.4,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142398095","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
Copper‐Catalyzed Oxidative Intramolecular Cyclization for the Synthesis of 2‐Hydroxy‐Indolin‐3‐Ones 铜催化氧化分子内环化合成 2-羟基-吲哚啉-3-酮
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-19 DOI: 10.1002/adsc.202400493
Haojie Ma , Fengyuan Zhou , Yuqi Li , Yuqi Zhang , Guosheng Huang , Xing Yang , Ji‐Jiang Wang
{"title":"Copper‐Catalyzed Oxidative Intramolecular Cyclization for the Synthesis of 2‐Hydroxy‐Indolin‐3‐Ones","authors":"Haojie Ma ,&nbsp;Fengyuan Zhou ,&nbsp;Yuqi Li ,&nbsp;Yuqi Zhang ,&nbsp;Guosheng Huang ,&nbsp;Xing Yang ,&nbsp;Ji‐Jiang Wang","doi":"10.1002/adsc.202400493","DOIUrl":"10.1002/adsc.202400493","url":null,"abstract":"<div><div>The synthesis of substituted 2‐hydroxy‐indolin‐3‐ones has attracted considerable attention due to the frequent presence of the indole nucleus in numerous natural products and biologically active molecules. Herein, a direct access to 2‐hydroxy‐indolin‐3‐ones through copper‐catalyzed oxidative intramolecular cyclization of <em>N</em>‐(2‐acetylphenyl)picolinamide has been developed. This method exhibits good functional group tolerance, atom‐economy and avoids the pre‐functionalization of substrates.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"366 22","pages":"Pages 4639-4643"},"PeriodicalIF":4.4,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141918660","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
β,β‐Disubstituted Alkan‐2‐ones from Propargylic Alcohols Combining a Meyer‐Schuster Rearrangement and Asymmetric Alkene Bioreduction 结合迈耶-舒斯特重排和不对称烯生物还原，从原炔醇制备β,β-二取代烷-2-酮
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-19 DOI: 10.1002/adsc.202400653
Lorena Escot , Sergio González‐Granda , Daniel Méndez‐Sánchez , Yu Wang , Helen C. Hailes , Iván Lavandera , Vicente Gotor‐Fernández
{"title":"β,β‐Disubstituted Alkan‐2‐ones from Propargylic Alcohols Combining a Meyer‐Schuster Rearrangement and Asymmetric Alkene Bioreduction","authors":"Lorena Escot ,&nbsp;Sergio González‐Granda ,&nbsp;Daniel Méndez‐Sánchez ,&nbsp;Yu Wang ,&nbsp;Helen C. Hailes ,&nbsp;Iván Lavandera ,&nbsp;Vicente Gotor‐Fernández","doi":"10.1002/adsc.202400653","DOIUrl":"10.1002/adsc.202400653","url":null,"abstract":"<div><div>The combination of a gold(I) N‐heterocyclic carbene complex and an ene‐reductase (ERED) has made possible the synthesis of enantiopure β,β‐disubstituted ketones in a one‐pot concurrent approach. The protocol consists of the Meyer‐Schuster rearrangement of racemic propargylic tertiary alcohols using [1,3‐bis(2,6‐diisopropylphenyl)imidazol‐2‐ylidene]‐[bis(trifluoromethanesulfonyl)‐imide]gold(I) (IPrAuNTf<sub>2</sub>), followed by an asymmetric alkene reduction of the α,β‐unsaturated ketone intermediate using the <em>Zymomonas mobilis</em> ERED (NCR‐ERED). The chemoenzymatic cascade was optimised with a model substrate, where <em>E</em>/<em>Z</em>‐isomers both generated the (<em>R</em>)‐ketone, which was rationalised using <em>in silico</em> molecular docking experiments. The cascade was then applied towards the production of a series of (<em>R</em>)‐4‐substituted‐alkan‐2‐ones in enantiopure form in a straightforward manner.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"366 22","pages":"Pages 4737-4746"},"PeriodicalIF":4.4,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/adsc.202400653","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141981069","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Zinc‐Mediated Carbamoyl Amination of Alkylidenecyclopropane‐Tethered Carbamoyl Chlorides: Synthesis of Functionalized 2‐Quinolones 锌介导的亚烷基环丙烷系氨基甲酰基氯的氨基甲酰基胺化反应：功能化 2-喹诺酮的合成
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-19 DOI: 10.1002/adsc.202400849
Jing‐Tong Deng , Ming Lang , Jin‐Bao Peng
{"title":"Zinc‐Mediated Carbamoyl Amination of Alkylidenecyclopropane‐Tethered Carbamoyl Chlorides: Synthesis of Functionalized 2‐Quinolones","authors":"Jing‐Tong Deng ,&nbsp;Ming Lang ,&nbsp;Jin‐Bao Peng","doi":"10.1002/adsc.202400849","DOIUrl":"10.1002/adsc.202400849","url":null,"abstract":"<div><div>The transition metal catalyzed cyclization of alkene‐tethered carbamoyl chloride has emerged as a tool to construct oxindoles bearing quaternary centers. Most of these reactions proceed via carbometalation‐initiated 5‐<em>exo</em>‐trig cyclization followed by nucleophilic trapping of the resulting <em>σ</em> alkyl‐metal species to achieve diverse functionalized oxindoles. The 6‐<em>endo</em>‐trig type cyclization of alkene‐tethered carbamoyl chloride has been rarely reported. Herein, a zinc‐mediated carbamoyl amination of alkylidenecyclopropane‐tethered carbamoyl chlorides with anilines for the synthesis of functionalized 2‐quinolones was developed. A range of different substituted 2‐quinolones were prepared in 65–89% yield from alkylidenecyclopropane‐tethered carbamoyl chlorides and aniline derivatives using a Zn/TMSCl system.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"366 22","pages":"Pages 4644-4648"},"PeriodicalIF":4.4,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142013977","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
Oxidative Photochemical Cyclisations to Access Spiroketals 通过氧化光化学环化反应获得螺环酮类化合物
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-19 DOI: 10.1002/adsc.202400393
Jonathan Trevorrow , Nhlanhla Sibanda , Anne O'Kearney‐McMullan , Lucie Miller Potucka , Adrian P. Dobbs
{"title":"Oxidative Photochemical Cyclisations to Access Spiroketals","authors":"Jonathan Trevorrow ,&nbsp;Nhlanhla Sibanda ,&nbsp;Anne O'Kearney‐McMullan ,&nbsp;Lucie Miller Potucka ,&nbsp;Adrian P. Dobbs","doi":"10.1002/adsc.202400393","DOIUrl":"10.1002/adsc.202400393","url":null,"abstract":"<div><div>The spiroketal moiety is an important substructure within many biological natural products. One method to access them is <em>via</em> the oxidative cyclisation of a pendant hydroxyl group on to a pre‐formed pyran. However applications of this methodology have been severely limited by requiring the use of toxic oxidants, such as lead (IV) tetraacetate or mercuric oxide. Herein we report a high yielding photochemical route to prepare complex spiroketals using an oxidative photochemical approach employing iodine monochloride and sodium acetate and demonstrate the methodology to the synthesis of a number of insect pheromones.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"366 22","pages":"Pages 4694-4701"},"PeriodicalIF":4.4,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/adsc.202400393","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141754290","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Emerging Trends for the Direct Synthesis of Dithiocarbamates 直接合成二硫代氨基甲酸盐的新趋势
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-19 DOI: 10.1002/adsc.202401011
Jiawei He , Xuesi Zhou , Xiang Liu
{"title":"Emerging Trends for the Direct Synthesis of Dithiocarbamates","authors":"Jiawei He ,&nbsp;Xuesi Zhou ,&nbsp;Xiang Liu","doi":"10.1002/adsc.202401011","DOIUrl":"10.1002/adsc.202401011","url":null,"abstract":"<div><div>Dithiocarbamates are common structural motifs in various bioactive compounds, attracting considerable attention due to their wide‐ranging applications in organic synthesis, material science, agrochemicals, and the pharmaceutical industry. Given the significant bioactivity and extensive applications of dithiocarbamates, the continuous pursuit of their efficient and diverse synthetic methods remains critical and urgent. Direct dithiocarbamation reactions can introduce −S−C(S)NR<sub>2</sub> group directly into parent molecules, providing shorter, greener, and more practical pathways for the synthesis of organodithiocarbamates. This article offers a comprehensive overview of the latest advancements in direct dithiocarbamation reactions, categorizing them based on the different sources of the −S−C(S)NR<sub>2</sub> group, with a particular emphasis on elucidating substrate scope and reaction mechanisms. Additionally, some synthetic limitations and applications of these methods are discussed. This review aims to provide the latest advancements in this field to both general readers and professional practitioners, inspiring innovative ideas for the synthesis of organosulfur compounds.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"366 22","pages":"Pages 4559-4584"},"PeriodicalIF":4.4,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142234418","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
Photochemically Induced Approaches to the Syntheses of β‐Lactams 光化学诱导的 β-内酰胺合成方法
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-19 DOI: 10.1002/adsc.202400715
Imtiaz Ahmed , Nikita Gupta , Ajit Kumar Gupta , Vijay Kumar Das
{"title":"Photochemically Induced Approaches to the Syntheses of β‐Lactams","authors":"Imtiaz Ahmed ,&nbsp;Nikita Gupta ,&nbsp;Ajit Kumar Gupta ,&nbsp;Vijay Kumar Das","doi":"10.1002/adsc.202400715","DOIUrl":"10.1002/adsc.202400715","url":null,"abstract":"<div><div>The synthesis of β‐lactam scaffolds is of paramount importance due to their extensive applications in pharmaceuticals, particularly as antibiotics. Visible light photocatalysis has emerged as a revolutionary approach in this domain, providing a sustainable and efficient pathway for β‐lactam construction. In this review, we meticulously discuss the recent developments in the synthesis of photocatalysed β‐lactam frameworks. A key focus is the Staudinger reaction, traditionally a cornerstone in β‐lactam synthesis, and its adaptation to visible light photocatalysis. We explore the mechanistic intricacies of the Staudinger reaction under photochemical conditions, along with other pivotal cyclization strategies enabled by visible light. By illuminating the novel photocatalytic routes to β‐lactams, this review provides a thorough understanding of the state‐of‐the‐art techniques and sets the stage for future innovations in the green synthesis of these critical compounds.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"366 22","pages":"Pages 4548-4558"},"PeriodicalIF":4.4,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142384390","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
Recent Advances in the Cascade Cyclization of Alkyne Units for the Construction of Benzofluorenes 用于制造苯并芴的炔烃单元级联环化的最新进展
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-19 DOI: 10.1002/adsc.202401047
Shimin Jiang , Ruchun Yang , Xian‐Rong Song , Qiang Xiao
{"title":"Recent Advances in the Cascade Cyclization of Alkyne Units for the Construction of Benzofluorenes","authors":"Shimin Jiang ,&nbsp;Ruchun Yang ,&nbsp;Xian‐Rong Song ,&nbsp;Qiang Xiao","doi":"10.1002/adsc.202401047","DOIUrl":"10.1002/adsc.202401047","url":null,"abstract":"<div><div>Benzofluorenes are an important class of polycyclic aromatic hydrocarbons (PAHs), which are widely used in materials science for light‐sensitive electronic components. In addition, the benzofluorene skeleton also serves as a key structural unit in various natural products. Therefore, the development of synthetic strategies for the construction of benzofluorenes has been a prominent research topic in synthetic chemistry. Over the past few decades, numerous efforts have been made for the construction of benzofluorenes <em>via</em> cascade cyclization of alkyne units. This review aims to summarize recent advances in the cascade cyclization of alkyne units for the construction of Based on the different reaction mechanisms underlying these transformations, this review can be divided into four categories: (1) thermal‐induced cascade cyclization of alkyne units for the construction of benzofluorenes, (2) metal‐catalyzed cascade cyclization of alkyne units for the construction of benzofluorenes, (3) acid‐promoted/catalyzed cyclization of alkyne units for the construction of benzofluorenes, and (4) base‐promoted cascade cyclization of alkyne units for the construction of benzofluorenes.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"366 22","pages":"Pages 4585-4605"},"PeriodicalIF":4.4,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142398607","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
Catalytic Strategies for the Selective Synthesis of α‐ and β‐Functionalized Amines via Hydrofunctionalization of Enamides 通过烯酰胺的氢官能化选择性合成 α 和 β 官能化胺的催化策略
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-19 DOI: 10.1002/adsc.202401172
Rui Sun , Xiao Yang
{"title":"Catalytic Strategies for the Selective Synthesis of α‐ and β‐Functionalized Amines via Hydrofunctionalization of Enamides","authors":"Rui Sun ,&nbsp;Xiao Yang","doi":"10.1002/adsc.202401172","DOIUrl":"10.1002/adsc.202401172","url":null,"abstract":"<div><div><em>α</em>‐ and <em>β</em>‐Functionalized amines are two classes of important compounds, whose structural units are widely present in approved drugs. The hydrofunctionalization of enamides is the most direct and efficient method for constructing these two types of compounds. Regioselectivity is the focus of this conversion, and is largely influenced by the catalytic mode. Therefore, to selectively synthesize <em>α</em>‐ or <em>β</em>‐functionalized amines, the progress in the catalytic hydrofunctionalization of enamides over the past decade is reviewed, and the catalytic pathways for this process discussed in detail. This account aims to objectively evaluate the effects of various catalytic pathways on the regioselectivity of hydrofunctionalization, to provide a new perspective on the selection of catalytic methods and the design of catalytic pathways for the selective synthesis of <em>α</em>‐ or <em>β</em>‐functionalized amines.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"366 22","pages":"Pages 4606-4617"},"PeriodicalIF":4.4,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142487049","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 of Ladderanes by Nickel‐Catalyzed Cyclodimerization of Allenynes: Scope and Mechanism 通过镍催化的阿伦炔环二聚化合成梯烷：范围和机理
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-19 DOI: 10.1002/adsc.202400676
Juan C. Nieto‐Carmona , M. Teresa Quirós , Iván Arribas‐Álvarez , Fernando Pérez‐Maseda , Marnix R. Kolk , Ana M. Martín Castro , Jorge Labrador‐Santiago , Elena Buñuel , Diego J. Cárdenas
{"title":"Synthesis of Ladderanes by Nickel‐Catalyzed Cyclodimerization of Allenynes: Scope and Mechanism","authors":"Juan C. Nieto‐Carmona ,&nbsp;M. Teresa Quirós ,&nbsp;Iván Arribas‐Álvarez ,&nbsp;Fernando Pérez‐Maseda ,&nbsp;Marnix R. Kolk ,&nbsp;Ana M. Martín Castro ,&nbsp;Jorge Labrador‐Santiago ,&nbsp;Elena Buñuel ,&nbsp;Diego J. Cárdenas","doi":"10.1002/adsc.202400676","DOIUrl":"10.1002/adsc.202400676","url":null,"abstract":"<div><div>We have developed a Ni‐catalyzed cyclodimerization of 1,6‐allenyenes which affords pentacyclic derivatives containing a [3]‐ladderane. Six new carbon‐carbon bonds are formed in a single operation which is fully atom‐economical. The reaction proceeds with an inexpensive catalyst and shows a broad scope in the alkyne, the allene and the tethering group. A computational and experimental study on the reaction mechanism suggests that this process proceeds by oxidative cyclometallation of the allenyne coordinated to Ni(0) followed by reductive elimination leading to cyclobutenes. Then, two of these molecules are coupled following a related cyclometallation‐reductive elimination sequence, the latter being the rate‐limiting step.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"366 22","pages":"Pages 4755-4764"},"PeriodicalIF":4.4,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/adsc.202400676","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141992027","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
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