Simple, environmentally benign and metal free one pot strategy has been used for the synthesis of 4-iodo-3-phenylbenzo[b][1,6]naphthyridine from O-alkynylquinolinyl aldehydes with tert-butyl amine and iodine through imine formation in good to excellent yield at room temperature in aerobic and mild conditions. The beauty of this reaction is the imine formation and cyclization in the same reaction pot. Due to presence of iodine in product, it can be useful for further reaction and can be valuable synthon for new organic compounds.
{"title":"One pot synthesis of 4-iodo-3-phenylbenzo[b][1,6]naphthyridine via imino iodization-cyclization of alkynylquinoline-3-carbaldehydes","authors":"Rashmi Singh , Vishal Prasad Sharma , Rajesh Kumar , Manish Raj , Tanu Gupta","doi":"10.1080/00397911.2024.2389542","DOIUrl":"10.1080/00397911.2024.2389542","url":null,"abstract":"<div><p>Simple, environmentally benign and metal free one pot strategy has been used for the synthesis of 4-iodo-3-phenylbenzo[<em>b</em>][1,6]naphthyridine from <em>O</em>-alkynylquinolinyl aldehydes with <em>tert</em>-butyl amine and iodine through imine formation in good to excellent yield at room temperature in aerobic and mild conditions. The beauty of this reaction is the imine formation and cyclization in the same reaction pot. Due to presence of iodine in product, it can be useful for further reaction and can be valuable synthon for new organic compounds.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 17","pages":"Pages 1462-1469"},"PeriodicalIF":1.8,"publicationDate":"2024-08-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142089297","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}
Pub Date : 2024-08-10DOI: 10.1080/00397911.2024.2390696
Cai Zhang
Trifluoromethyl heterocyclic compounds have high lipophilicity, metabolic stability and binding selectivity, so it is very important to develop their synthetic methods. This review provides an overview of synthesis of trifluoromethyl substituted heterocyclic compounds from β-trifluoromethylated acrylates over the period from 2018 to the present.
{"title":"Synthesis of trifluoromethyl substituted heterocyclic compounds with β-trifluoromethylated acrylates","authors":"Cai Zhang","doi":"10.1080/00397911.2024.2390696","DOIUrl":"10.1080/00397911.2024.2390696","url":null,"abstract":"<div><div>Trifluoromethyl heterocyclic compounds have high lipophilicity, metabolic stability and binding selectivity, so it is very important to develop their synthetic methods. This review provides an overview of synthesis of trifluoromethyl substituted heterocyclic compounds from β-trifluoromethylated acrylates over the period from 2018 to the present.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 20","pages":"Pages 1707-1724"},"PeriodicalIF":1.8,"publicationDate":"2024-08-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142216151","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}
Pub Date : 2024-08-06DOI: 10.1080/00397911.2024.2387810
Dattatray D. Gaikwad , Sachin A. Dhawale , Chandrakant D. Pawar , Dattatraya N. Pansare , Umakant D. Pawar , Ashok M. Zine
The present work aimed to synthesize different substituted glycinamide derivatives. A series of novel substituted 2-((N-benzyl-5-bromo-2-methoxyphenyl) sulfonamide) and their glycinamide derivatives (5a–5p) were synthesized. We developed a simple strategy for synthesizing functionally diverse sulfonamide and glycinamide derivatives through a series of steps. A series of molecules containing amide derivatives were designed and synthesized, and their structures were elucidated and confirmed by1H NMR, 13 C NMR, LCMS, and their purity was checked using HPLC. The synthesized compounds were screened for anticancer activity against A-549 and A431 cancer cell lines by MTT assay and then docking studies were carried out to understand the molecular interactions. The preliminary bioassay suggests that most compounds showed remarkable anti-proliferation activity. Gefitinib was used as a positive control. The compounds 5g and 5f were active compared with Gefitinib in both the cell lines.
{"title":"Synthesis, antiproliferative activity and insilco studies of substituted 2-((N-benzyl-5-bromo-2-methoxyphenyl) sulfonamide) glycinamide derivatives","authors":"Dattatray D. Gaikwad , Sachin A. Dhawale , Chandrakant D. Pawar , Dattatraya N. Pansare , Umakant D. Pawar , Ashok M. Zine","doi":"10.1080/00397911.2024.2387810","DOIUrl":"10.1080/00397911.2024.2387810","url":null,"abstract":"<div><p>The present work aimed to synthesize different substituted glycinamide derivatives. A series of novel substituted 2-((N-benzyl-5-bromo-2-methoxyphenyl) sulfonamide) and their glycinamide derivatives <strong>(5a–5p)</strong> were synthesized. We developed a simple strategy for synthesizing functionally diverse sulfonamide and glycinamide derivatives through a series of steps. A series of molecules containing amide derivatives were designed and synthesized, and their structures were elucidated and confirmed by1H NMR, 13 C NMR, LCMS, and their purity was checked using HPLC. The synthesized compounds were screened for anticancer activity against A-549 and A431 cancer cell lines by MTT assay and then docking studies were carried out to understand the molecular interactions. The preliminary bioassay suggests that most compounds showed remarkable anti-proliferation activity. Gefitinib was used as a positive control. The compounds <strong>5g</strong> and <strong>5f</strong> were active compared with Gefitinib in both the cell lines.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 17","pages":"Pages 1423-1432"},"PeriodicalIF":1.8,"publicationDate":"2024-08-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142089311","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}
Pub Date : 2024-08-05DOI: 10.1080/00397911.2024.2387134
Magdy A Ibrahim , Mohamed Abdel-Megid , Osama Farouk , Nasser M. El-Gohary , Asmaa I Nabeel , Marwa M. A. Attai , Al-Shimaa Badran
The chemical reactivity of 3-formylchromones toward several carbon and nitrogen nucleophiles is collected in this review. Certain annulated chromones and 3-heteroaryl chromones were synthesized. A diversity of three component reactions including 3-formylchromones was also summarized.
{"title":"Nucleophilic reactions with 3-formylchromones: A decade update","authors":"Magdy A Ibrahim , Mohamed Abdel-Megid , Osama Farouk , Nasser M. El-Gohary , Asmaa I Nabeel , Marwa M. A. Attai , Al-Shimaa Badran","doi":"10.1080/00397911.2024.2387134","DOIUrl":"10.1080/00397911.2024.2387134","url":null,"abstract":"<div><p>The chemical reactivity of 3-formylchromones toward several carbon and nitrogen nucleophiles is collected in this review. Certain annulated chromones and 3-heteroaryl chromones were synthesized. A diversity of three component reactions including 3-formylchromones was also summarized.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 18","pages":"Pages 1495-1522"},"PeriodicalIF":1.8,"publicationDate":"2024-08-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142172956","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}
Pub Date : 2024-08-02DOI: 10.1080/00397911.2024.2379447
Jiming Liu , Xinghua Zheng , Wenjun Luo , Zhengwang Chen , Fei Ling
An eco-friendly, metal-free approach for synthesizing dihydrobenzo[b][1,8]naphthyridine derivatives has been established. This method employs ortho-chloroquinolin-α,β-unsaturated ketones as dipolarophiles and acyclic enaminones as amphiphilic nucleophiles, enabling a formal [3 + 3] annulation reaction under phase-transfer catalysis to offed the targeted products. It boasts transition-metal-free conditions, broad functional group compatibility, and straightforward operational procedures.
{"title":"TBAB-catalyzed assisted C-C/C-N bond formations: An efficient approach to dihydrobenzo[b][1,8]naphthyridin derivatives via metal free Cascade annulation","authors":"Jiming Liu , Xinghua Zheng , Wenjun Luo , Zhengwang Chen , Fei Ling","doi":"10.1080/00397911.2024.2379447","DOIUrl":"10.1080/00397911.2024.2379447","url":null,"abstract":"<div><p>An eco-friendly, metal-free approach for synthesizing dihydrobenzo[<em>b</em>][1,8]naphthyridine derivatives has been established. This method employs <em>ortho</em>-chloroquinolin-α,β-unsaturated ketones as dipolarophiles and acyclic enaminones as amphiphilic nucleophiles, enabling a formal [3 + 3] annulation reaction under phase-transfer catalysis to offed the targeted products. It boasts transition-metal-free conditions, broad functional group compatibility, and straightforward operational procedures.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 15","pages":"Pages 1252-1262"},"PeriodicalIF":1.8,"publicationDate":"2024-08-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141942790","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}
Pub Date : 2024-08-02DOI: 10.1080/00397911.2024.2381074
Chang-Seok Hyun , Joohwan Eo , Ji Eon Kwon , Byeong-Kwan An
1,4,5,8-tetrasubstituted dihyroanthracene-based triptycene trisquinones (TT) molecules, THAO-TT and tris(THAO)-TT, were synthesized by Diels–Alder reaction between TT and 1,4,5,8-tetrakis(hexyloxy)anthracene to produce the extended triptycene derivatives containing electron-accepting functionality. The prepared THOA-TT and tris(THOA)-TT exhibited excellent thermal stability owing to the rigid TT framework. The optical and redox properties of THOA-TT and tris(THOA)-TT were controlled by the homoconjugation between the benzoquinone units and the peripheral units through the connecting methine groups.
{"title":"1,4,5,8-tetrasubstituted dihydroanthracene-based triptycene trisquinones: Synthesis, structural, and physicochemical characterization","authors":"Chang-Seok Hyun , Joohwan Eo , Ji Eon Kwon , Byeong-Kwan An","doi":"10.1080/00397911.2024.2381074","DOIUrl":"10.1080/00397911.2024.2381074","url":null,"abstract":"<div><p>1,4,5,8-tetrasubstituted dihyroanthracene-based triptycene trisquinones (TT) molecules, THAO-TT and <em>tris</em>(THAO)-TT, were synthesized by Diels–Alder reaction between TT and 1,4,5,8-tetrakis(hexyloxy)anthracene to produce the extended triptycene derivatives containing electron-accepting functionality. The prepared THOA-TT and <em>tris</em>(THOA)-TT exhibited excellent thermal stability owing to the rigid TT framework. The optical and redox properties of THOA-TT and <em>tris</em>(THOA)-TT were controlled by the homoconjugation between the benzoquinone units and the peripheral units through the connecting methine groups.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 15","pages":"Pages 1263-1272"},"PeriodicalIF":1.8,"publicationDate":"2024-08-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141802653","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}
Pub Date : 2024-08-02DOI: 10.1080/00397911.2024.2382784
Samar Argoubi , M. A. Sanhoury , I. Zerough , E. Manoury , I. Chehidi
Seventeen new highly fluorinated phosphoramidates containing alkylamino moieties of the type (RFO)2P(O)NHR (R = CH2CH2CH3, (CH2)3CH3, (CH2)4-CH3, CH(CH3)2, C6H11, CH2CH2-C6H5, CH2-C6H5 or C6H5; RF = CH2CF3, CH2C2F5 or CH2CH2C6F13) were synthesized. These compounds were obtained through the reaction of primary amines with bis(polyfluoroalkyl)phosphites as phosphorylating agents, using molecular iodine as a mild catalyst and in the presence of H2O2.This method was chosen out of various literature common methods, which were thoroughly investigated using 31P NMR spectroscopy. In addition, the variation in reaction rates among different phosphites was studied and compared with previous research findings. The title phosphoramidates were fully characterized using multinuclear (1H,13C,31P, and 19F) NMR, IR, and HRMS techniques.
{"title":"Synthesis and characterization of new highly fluorinated phosphoramidates bearing different alkylamino groups","authors":"Samar Argoubi , M. A. Sanhoury , I. Zerough , E. Manoury , I. Chehidi","doi":"10.1080/00397911.2024.2382784","DOIUrl":"10.1080/00397911.2024.2382784","url":null,"abstract":"<div><p>Seventeen new highly fluorinated phosphoramidates containing alkylamino moieties of the type (R<sub>F</sub>O)<sub>2</sub>P(O)NHR (R = CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>, (CH<sub>2</sub>)<sub>3</sub>CH<sub>3</sub>, (CH<sub>2</sub>)<sub>4</sub>-CH<sub>3</sub>, CH(CH<sub>3</sub>)<sub>2</sub>, C<sub>6</sub>H<sub>11</sub>, CH<sub>2</sub>CH<sub>2</sub>-C<sub>6</sub>H<sub>5</sub>, CH<sub>2</sub>-C<sub>6</sub>H<sub>5</sub> or C<sub>6</sub>H<sub>5</sub>; R<sub>F</sub> = CH<sub>2</sub>CF<sub>3</sub>, CH<sub>2</sub>C<sub>2</sub>F<sub>5</sub> or CH<sub>2</sub>CH<sub>2</sub>C<sub>6</sub>F<sub>13</sub>) were synthesized. These compounds were obtained through the reaction of primary amines with bis(polyfluoroalkyl)phosphites as phosphorylating agents, using molecular iodine as a mild catalyst and in the presence of H<sub>2</sub>O<sub>2.</sub>This method was chosen out of various literature common methods, which were thoroughly investigated using <sup>31</sup>P NMR spectroscopy. In addition, the variation in reaction rates among different phosphites was studied and compared with previous research findings. The title phosphoramidates were fully characterized using multinuclear (<sup>1</sup>H,<sup>13</sup>C,<sup>31</sup>P, and <sup>19</sup>F) NMR, IR, and HRMS techniques.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 15","pages":"Pages 1273-1283"},"PeriodicalIF":1.8,"publicationDate":"2024-08-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141813488","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}
Pub Date : 2024-08-02DOI: 10.1080/00397911.2024.2377738
Pyridines and its derivatives are an important class of heterocyclic compounds of low molecular weight. They have been used in the treatment of a various diseases like cardiovascular disease, antioxidant, antibacterial, anti-tubercular, anticancer, anticoagulant, etc. In 1882, Arthur Hantzsch reported pyridine derivative synthesis using different aldehydes, 2 molecules β-keto ester and ammonium acetate to give a Hantzsch ester or 1,4-dihydropyridine derivatives. This review article focuses on different protocols for Hantzsch reaction using different catalysts like β-cyclodextrin–polyurethane polymer (β-CDPU), chitosan nanoparticles (NPs), salicylic acid, p-toluenesulfonic acid (p-TSA), alginic acid, Fe-TUD-1, PdRuNi@GO, Ceric Ammonium Nitrate (CAN), sulfate polyborate, etc. for the synthesis of pyridine derivatives.
{"title":"Hantzsch reaction: The important key for pyridine/dihydropyridine synthesis","authors":"","doi":"10.1080/00397911.2024.2377738","DOIUrl":"10.1080/00397911.2024.2377738","url":null,"abstract":"<div><p>Pyridines and its derivatives are an important class of heterocyclic compounds of low molecular weight. They have been used in the treatment of a various diseases like cardiovascular disease, antioxidant, antibacterial, anti-tubercular, anticancer, anticoagulant, etc. In 1882, Arthur Hantzsch reported pyridine derivative synthesis using different aldehydes, 2 molecules β-keto ester and ammonium acetate to give a Hantzsch ester or 1,4-dihydropyridine derivatives. This review article focuses on different protocols for Hantzsch reaction using different catalysts like β-cyclodextrin–polyurethane polymer (β-CDPU), chitosan nanoparticles (NPs), salicylic acid, p-toluenesulfonic acid (p-TSA), alginic acid, Fe-TUD-1, PdRuNi@GO, Ceric Ammonium Nitrate (CAN), sulfate polyborate, etc. for the synthesis of pyridine derivatives.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 15","pages":"Pages 1221-1244"},"PeriodicalIF":1.8,"publicationDate":"2024-08-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141584941","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}
Pub Date : 2024-08-02DOI: 10.1080/00397911.2024.2380063
Kota Fujihara , Hatsuo Yamamura , Atsushi Miyagawa
Sugar nucleotides are essential substrates used for synthesizing bioactive oligosaccharides in enzymatic reactions, however, their preparation via chemical and enzyme reactions is challenging. Therefore, we investigated the synthesis of sugar nucleotides under optimal conditions using a facile one-step reaction. Seven sugar nucleotides were synthesized via an optimized one-step reaction in 40–80% yield, exhibiting a preference for 1,2-trans glycoside. Moreover, a gram-scale synthesis of UDP-galactose resulted in a 46% (578 mg) yield.
{"title":"One-step synthesis of sugar nucleotides under optimized conditions","authors":"Kota Fujihara , Hatsuo Yamamura , Atsushi Miyagawa","doi":"10.1080/00397911.2024.2380063","DOIUrl":"10.1080/00397911.2024.2380063","url":null,"abstract":"<div><p>Sugar nucleotides are essential substrates used for synthesizing bioactive oligosaccharides in enzymatic reactions, however, their preparation via chemical and enzyme reactions is challenging. Therefore, we investigated the synthesis of sugar nucleotides under optimal conditions using a facile one-step reaction. Seven sugar nucleotides were synthesized via an optimized one-step reaction in 40–80% yield, exhibiting a preference for 1,2-trans glycoside. Moreover, a gram-scale synthesis of UDP-galactose resulted in a 46% (578 mg) yield.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 15","pages":"Pages 1245-1251"},"PeriodicalIF":1.8,"publicationDate":"2024-08-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141829533","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}
Reaction of 9-fluorene propargylic alcohols and substituted-2-hydrazinopyridine using BF3·OEt2 as a Lewis acid catalyst afforded 9-fluorenlidene appended 2-hydrazinopyridine imine derivatives has been developed. The scope of the reaction is demonstrated by selecting a range of fluorene propargylic alcohols and substituted 2-hydrazinopyridine imines. All the synthesized molecules were characterized using various spectroscopic and analytical techniques including 1H NMR,13C NMR, and Mass spectrometry. A plausible reaction mechanism for forming title compounds via propargylic allenyl carbocation is postulated. The synthetic utility of products thus formed is demonstrated by utilizing Suzuki coupling.
{"title":"BF3‧OEt2 promoted synthesis of 9-fluorenlidene appended 2-hydrazinopyridine imines from (phenylethynyl)-fluorene and 2-hydrazinopyridine derivatives","authors":"Suresh Snoxma Smile , Harichandran Gurusamy , Ponnusamy Shanmugam","doi":"10.1080/00397911.2024.2385538","DOIUrl":"10.1080/00397911.2024.2385538","url":null,"abstract":"<div><p>Reaction of 9-fluorene propargylic alcohols and substituted-2-hydrazinopyridine using BF<sub>3</sub>·OEt<sub>2</sub> as a Lewis acid catalyst afforded 9-fluorenlidene appended 2-hydrazinopyridine imine derivatives has been developed. The scope of the reaction is demonstrated by selecting a range of fluorene propargylic alcohols and substituted 2-hydrazinopyridine imines. All the synthesized molecules were characterized using various spectroscopic and analytical techniques including <sup>1</sup>H NMR,<sup>13</sup>C NMR, and Mass spectrometry. A plausible reaction mechanism for forming title compounds via propargylic allenyl carbocation is postulated. The synthetic utility of products thus formed is demonstrated by utilizing Suzuki coupling.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 17","pages":"Pages 1413-1422"},"PeriodicalIF":1.8,"publicationDate":"2024-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141882958","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}