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Photoinduced Radical Annulations of Tetrahydroisoquinoline Derivatives with 2-Benzothiazolimines: Highly Diastereoselective Synthesis of Fused Hexahydroimidazo[2,1-a]isoquinolines. 四氢异喹啉衍生物与 2-苯并噻唑亚胺的光诱导自由基嵌合：高非对映选择性合成融合六氢咪唑并[2,1-a]异喹啉。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-20 Epub Date: 2024-09-06 DOI: 10.1021/acs.joc.4c01691
Bing Yi, Wenhui Zhang, Zi-Qi Yi, Fei Chen, Qianqian Zeng, Niannian Yi, Li Lv, Fan Zhang, Yanjun Xie, Jian-Ping Tan
{"title":"Photoinduced Radical Annulations of Tetrahydroisoquinoline Derivatives with 2-Benzothiazolimines: Highly Diastereoselective Synthesis of Fused Hexahydroimidazo[2,1-<i>a</i>]isoquinolines.","authors":"Bing Yi, Wenhui Zhang, Zi-Qi Yi, Fei Chen, Qianqian Zeng, Niannian Yi, Li Lv, Fan Zhang, Yanjun Xie, Jian-Ping Tan","doi":"10.1021/acs.joc.4c01691","DOIUrl":"10.1021/acs.joc.4c01691","url":null,"abstract":"<p><p>We report herein a photoinduced radical 1,3-dipolar cycloaddition between the 2-benzothiazolimines and tetrahydroisoquinoline derivatives with an organo-photocatalyst. A variety of benzothiazole-based hexahydroimidazo[2,1-<i>a</i>]isoquinoline architectures with great synthetic value were conveniently and efficiently constructed in moderate to good yields and excellent diastereoselectivities with highly tolerant functional groups. Moreover, the practicality and utility of this protocol were demonstrated by scale-up synthesis and facile elaboration. Preliminary mechanistic investigations indicated that the reaction proceeded via a visible-light-induced radical 1,3-dipolar cycloaddition pathway. This finding is expected to stimulate a more extensive exploration of the green and concise synthesis of structurally diverse heterocyclic molecules in the synthetic community.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142142998","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 Cross-Coupling of Aryl Bromides and Chlorides with Trimethylsilylalkynes under Mild Conditions. 在温和条件下钯催化芳基溴化物和氯化物与三甲基硅烷的交叉偶联。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-20 Epub Date: 2024-09-02 DOI: 10.1021/acs.joc.4c01499
Adrian Tlahuext-Aca, Quyen D Nguyen, Yang Gao, Girish C Sati, Jinpeng Zhao, Daniel Valco
{"title":"Palladium-Catalyzed Cross-Coupling of Aryl Bromides and Chlorides with Trimethylsilylalkynes under Mild Conditions.","authors":"Adrian Tlahuext-Aca, Quyen D Nguyen, Yang Gao, Girish C Sati, Jinpeng Zhao, Daniel Valco","doi":"10.1021/acs.joc.4c01499","DOIUrl":"10.1021/acs.joc.4c01499","url":null,"abstract":"<p><p>Herein, we disclose a palladium-catalyzed cross-coupling of aryl bromides and chlorides with trimethylsilylalkynes under mild reaction conditions. This method utilizes commercially available and air stable palladium precatalysts and avoids the use of copper cocatalysts. Moreover, it allows for the synthesis of a wide range of disubstituted alkynes in high yields with excellent functional group tolerance. The utility of the developed method was further demonstrated via the late-stage alkynylation of pharmaceuticals and natural bioactive compounds.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142102221","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 Spiropyrrolines via One-Pot Tf2O-Mediated Amide Activation/Formal [3 + 2]-Cycloaddition of α-Formylamino Ketones. 通过 Tf2O 介导的α-甲酰基氨基酮的一锅酰胺活化/正 式 [3 + 2]- 环加成法合成螺吡咯啉。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-20 Epub Date: 2024-09-04 DOI: 10.1021/acs.joc.4c01128
Khanh-Toan Ho, Joshua G Pierce
{"title":"Synthesis of Spiropyrrolines <i>via</i> One-Pot Tf<sub>2</sub>O-Mediated Amide Activation/Formal [3 + 2]-Cycloaddition of α-Formylamino Ketones.","authors":"Khanh-Toan Ho, Joshua G Pierce","doi":"10.1021/acs.joc.4c01128","DOIUrl":"10.1021/acs.joc.4c01128","url":null,"abstract":"<p><p>An efficient method for the synthesis of spiropyrrolines from readily accessible α-formylamino ketones is reported. The method involves amide activation using Tf<sub>2</sub>O, followed by a formal [3 + 2]-cycloaddition of the resulting enolic nitrilium intermediate with Michael acceptors, ultimately affording spiropyrrolines. Mechanistic insights were gained through NMR studies, elucidating the precise role of the base additive and suggesting the formation of an enolic nitrilium intermediate.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142124216","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
Magnesium-Mediated Cross-Electrophile Couplings of Aryl 2-Pyridyl Esters with Aryl Bromides for Ketone Synthesis through In Situ-Formed Arylmagnesium Intermediates. 镁介导的芳基 2-吡啶酯与芳基溴化物的交叉亲电偶联，通过原位形成的芳基镁中间体合成酮。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-20 Epub Date: 2024-09-09 DOI: 10.1021/acs.joc.4c01851
Xiao-Wei Han, Yuan He, Chao Gui, Xue-Qiang Chu, Xue-Fei Zhao, Xu-Hong Hu, Xiaocong Zhou, Weidong Rao, Zhi-Liang Shen
{"title":"Magnesium-Mediated Cross-Electrophile Couplings of Aryl 2-Pyridyl Esters with Aryl Bromides for Ketone Synthesis through In Situ-Formed Arylmagnesium Intermediates.","authors":"Xiao-Wei Han, Yuan He, Chao Gui, Xue-Qiang Chu, Xue-Fei Zhao, Xu-Hong Hu, Xiaocong Zhou, Weidong Rao, Zhi-Liang Shen","doi":"10.1021/acs.joc.4c01851","DOIUrl":"10.1021/acs.joc.4c01851","url":null,"abstract":"<p><p>Aryl 2-pyridyl esters could efficiently undergo cross-electrophile couplings with aryl bromides with the aid of magnesium as a reducing metal in the absence of a transition-metal catalyst, leading to the unsymmetrical diaryl ketones in modest to good yields with wide functionality compatibility. In addition, the reaction could be easily scaled up and applied in the late-stage modification of biologically active molecules. Preliminary mechanistic study showed that the coupling reaction presumably proceeds through the in situ formation of arylmagnesium reagents as key intermediates.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142152468","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
(±)-Salvicatone A: A Pair of C27-Meroterpenoid Enantiomers with Skeletons from the Roots and Rhizomes of Salvia castanea Diels f. tomentosa Stib. (±)-Salvicatone A:一组具有骨架的C27-Meroterpenoid对映体，来自鼠尾草根和根茎。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-20 Epub Date: 2023-11-17 DOI: 10.1021/acs.joc.3c01664
Dong-Dong Wang, Rui Zhang, Lian-Yu Tang, Guo-Qing Long, Hui Yan, Yong-Cheng Yang, Zi-Feng Guo, Ying-Ying Zheng, Yong Wang, Jing-Ming Jia, An-Hua Wang
{"title":"(±)-Salvicatone A: A Pair of C<sub>27</sub>-Meroterpenoid Enantiomers with Skeletons from the Roots and Rhizomes of <i>Salvia castanea</i> Diels f. <i>tomentosa</i> Stib.","authors":"Dong-Dong Wang, Rui Zhang, Lian-Yu Tang, Guo-Qing Long, Hui Yan, Yong-Cheng Yang, Zi-Feng Guo, Ying-Ying Zheng, Yong Wang, Jing-Ming Jia, An-Hua Wang","doi":"10.1021/acs.joc.3c01664","DOIUrl":"10.1021/acs.joc.3c01664","url":null,"abstract":"<p><p>(±)-Salvicatone A (<b>1</b>), a C<sub>27</sub>-meroterpenoid featuring a unique 6/6/6/6/6-pentacyclic carbon skeleton with a 7,8,8a,9,10,10a-hexahydropyren-1 (<i>6H</i>)-one motif, was isolated from the roots and rhizomes of <i>Salvia castanea</i> Diels <i>f. tomentosa</i> Stib. Its structure was characterized by comprehensive spectroscopic analyses along with computer-assisted structure elucidation, including ACD/structure elucidator and quantum chemical calculations with <sup>1</sup>H/<sup>13</sup>C NMR and electronic circular dichroism. Biogenetically, compound <b>1</b> was constructed from decarboxylation following [4 + 2] Diels-Alder cycloaddition reaction between caffeic acid and miltirone analogue. Bioassays showed that (-)-<b>1</b> and (+)-<b>1</b> inhibited nitric oxide production in lipopolysaccharide-induced RAW264.7 macrophage cells with an IC<sub>50</sub> value of 6.48 ± 1.25 and 15.76 ± 5.55 μM, respectively. The structure-based virtual screening based on the pharmacophores in ePharmaLib, as well as the molecular docking and molecular dynamics simulations study, implied that (-)-<b>1</b> and (+)-<b>1</b> may potentially bind to retinoic acid receptor-related orphan receptor C to exert anti-inflammatory activities.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"136395269","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
Semiheterogeneous Photoredox Catalysis: Synthesis of 3-Sulfonylquinolines via Radical Multicomponent Cascade Annulation. 半均相光氧化催化：通过自由基多组分级联嵌合合成 3-磺酰基喹啉。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-20 Epub Date: 2024-09-02 DOI: 10.1021/acs.joc.4c01604
Xiao Li, Jun Jiang, Xiang Chen, Wei-Min He
{"title":"Semiheterogeneous Photoredox Catalysis: Synthesis of 3-Sulfonylquinolines via Radical Multicomponent Cascade Annulation.","authors":"Xiao Li, Jun Jiang, Xiang Chen, Wei-Min He","doi":"10.1021/acs.joc.4c01604","DOIUrl":"10.1021/acs.joc.4c01604","url":null,"abstract":"<p><p>An efficient photocatalytic protocol combining heterogeneous semiconductors as photocatalysts and NHPI as a redox reagent was disclosed. Under this protocol, 3-sulfonylquinolines were formed in up to 92% yield via a multicomponent radical cascade annulation. Good substituent tolerance and gram-scale reaction showed the potential in fine chemicals modification and pharmaceutical synthesis.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142102222","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 Diarylalkanes by Photoreductive 1,2-Diarylation of Alkenes with Aryl Halides and Cyanoaromatics. 用芳基卤化物和氰基芳烃对烯烃进行 1,2-二芳基化的光感应合成二烷。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-20 Epub Date: 2024-09-05 DOI: 10.1021/acs.joc.4c01830
Liang Zeng, Xuan-Hui Ouyang, De-Liang He, Jin-Heng Li
{"title":"Synthesis of Diarylalkanes by Photoreductive 1,2-Diarylation of Alkenes with Aryl Halides and Cyanoaromatics.","authors":"Liang Zeng, Xuan-Hui Ouyang, De-Liang He, Jin-Heng Li","doi":"10.1021/acs.joc.4c01830","DOIUrl":"10.1021/acs.joc.4c01830","url":null,"abstract":"<p><p>We report a visible light-induced photoreductive strategy for three-component diarylation of alkenes with aryl halides and cyanoaromatics. Upon photoredox catalysis and with tertiary alkyl amines as the electron transfer agent, aryl halides selectively undergo halogen atom transfer to generate the aryl radicals and two C(sp<sup>2</sup>)-C(sp<sup>3</sup>) bonds between the cabron atoms are created in a radical addition and radical-radical coupling fashion to rapidly assemble diverse functionalized polyarylalkanes with high regio- and chemoselectivity. This method can be applied to broad feedstocks, including terminal alkenes, internal alkenes, aryl iodides, aryl bromides, aryl chlorides, electron-deficient benzonitriles, and isonicotinonitriles.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142131203","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
Decarboxylation of Aza-Annulation Products as a Synthetic Route to 3-Pyrrolin-2-ones and 1,2,3,4-Tetrahydropyridin-2-ones. 作为 3-吡咯啉-2-酮和 1,2,3,4-四氢吡啶-2-酮合成途径的氮杂环氧化产物的脱羧反应。
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-19 DOI: 10.1021/acs.joc.4c01838
Kseniia Petrova,Almaz Kaipov,Lyailya Yussupova,Iliyas Iznat,Davit Hayrapetyan
{"title":"Decarboxylation of Aza-Annulation Products as a Synthetic Route to 3-Pyrrolin-2-ones and 1,2,3,4-Tetrahydropyridin-2-ones.","authors":"Kseniia Petrova,Almaz Kaipov,Lyailya Yussupova,Iliyas Iznat,Davit Hayrapetyan","doi":"10.1021/acs.joc.4c01838","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01838","url":null,"abstract":"Aza-annulation of enamines derived from β-ketoesters with maleic and itaconic anhydrides proceeds with excellent diastereoselectivity to provide functionalized γ- and δ-lactams. Further hydrolysis of the aza-annulation products resulted in dicarboxylic acids that underwent spontaneous decarboxylation under ambient conditions. The decarboxylation of β-γ unsaturated carboxylic acids with an electron-rich enamide C═C bond proceeds with the migration of the C═C bond and serves as a practical synthetic entry into 3-pyrrolin-2-ones and 1,2,3,4-tetrahydropyridin-2-ones.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-09-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142246981","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
Rh(III)- or Ru(II)-Catalyzed C–H Annulation with Vinylene Carbonate and an Unexpected Aerobic Oxidation/Deprotection Cascade to Yield Cinnolin-4(1H)-ones Rh(III)或 Ru(II)-Catalyzed C-H Annulation with Vinylene Carbonate and an Unexpected Aerobic Oxidation/Deprotection Cascade to Yield Cinnolin-4(1H)-ones
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-19 DOI: 10.1021/acs.joc.4c01672
Yuqin Wang, Yiling Zeng, Yi Xiao, Jinhua Wang, Shiqing Li
{"title":"Rh(III)- or Ru(II)-Catalyzed C–H Annulation with Vinylene Carbonate and an Unexpected Aerobic Oxidation/Deprotection Cascade to Yield Cinnolin-4(1H)-ones","authors":"Yuqin Wang, Yiling Zeng, Yi Xiao, Jinhua Wang, Shiqing Li","doi":"10.1021/acs.joc.4c01672","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01672","url":null,"abstract":"Transition metal-catalyzed C–H annulation reactions have been extensively utilized for the synthesis of cinnolines, especially the N-protected ones; however, none of them can yield cinnolin-4(1<i>H</i>)-ones, a significant class of bioactive skeletons. Herein, we disclose one-pot access to cinnolin-4(1<i>H</i>)-ones through Rh(III)- or Ru(II)-catalyzed C–H activation/annulation of <i>N</i>-aryl cyclic hydrazides with vinylene carbonate, followed by an O<sub>2</sub>/K<sub>2</sub>CO<sub>3</sub>-promoted aerobic oxidation/deprotection cascade. The π-conjugation of the directing groups plays a crucial role in facilitating this transformation. Notably, seven-membered enolic Rh species <b>IMC</b> is characterized via electrospray ionization mass spectroscopy for the first time, which, along with systematic control experiments, provides compelling evidence for the mechanistic pathway encompassing alkenyl insertion, β-oxygen elimination, protonation, and dehydration.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-09-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142247228","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
Low-Cost, Safe, and Anion-Flexible Method for the Electrosynthesis of Diaryliodonium Salts 低成本、安全且阴离子灵活的二碘鎓盐电合成方法
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-19 DOI: 10.1021/acs.joc.4c01521
Anton Scherkus, Aija Gudkova, Jan Čada, Bernd H. Müller, Tomas Bystron, Robert Francke
{"title":"Low-Cost, Safe, and Anion-Flexible Method for the Electrosynthesis of Diaryliodonium Salts","authors":"Anton Scherkus, Aija Gudkova, Jan Čada, Bernd H. Müller, Tomas Bystron, Robert Francke","doi":"10.1021/acs.joc.4c01521","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01521","url":null,"abstract":"An electrochemical approach toward the synthesis of diaryliodonium salts based on anodic C–I coupling between aryl iodides and arenes is presented. In contrast to previous protocols, our method requires no chemical oxidants, strong acids, or fluorinated solvents. A further advantage is that by use of the appropriate supporting electrolyte, the counterion of choice can be introduced, which is time- and cost-saving as compared to postsynthesis ion exchange. This “anion-flexibility” is particularly interesting when considering the pronounced effect of the counterion on the reactivity of diaryliodonium species in aryl transfer reactions. The scope of our method comprises 24 examples with isolated yields of up to 99%. Scalability was demonstrated by the synthesis on a gram scale. Furthermore, it was shown that the diaryliodonium-containing post-electrolysis solution can be used without further workup as a reactive medium for <i>O</i>-arylation reactions. Finally, a series of <i>para</i>-substituted diaryliodonium compounds was studied using linear sweep voltammetry on a microelectrode and analyzed with respect to the influence of the electronic structure on the redox behavior.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-09-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142247229","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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