Organic Process Research & Development最新文献

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Oxygen-, Nitrogen-, and Sulfur-Containing Heterocycles: Recent Advances in De Novo Synthesis and Prospect 含氧、氮和硫的杂环:新合成的最新进展与展望
IF 3.4 3区 化学
Organic Process Research & Development Pub Date : 2024-07-13 DOI: 10.1021/acs.oprd.4c00186
Yongpeng Zheng, Jianxiao Li, Wanqing Wu, Chaorong Qi, Huanfeng Jiang
{"title":"Oxygen-, Nitrogen-, and Sulfur-Containing Heterocycles: Recent Advances in De Novo Synthesis and Prospect","authors":"Yongpeng Zheng, Jianxiao Li, Wanqing Wu, Chaorong Qi, Huanfeng Jiang","doi":"10.1021/acs.oprd.4c00186","DOIUrl":"https://doi.org/10.1021/acs.oprd.4c00186","url":null,"abstract":"Oxygen-, nitrogen-, and sulfur-containing heterocycles exhibit remarkable biological and pharmaceutical activities that are often found in naturally occurring products, pharmaceutical molecules, and synthetic compounds. Therefore, the synthesis of heterocycle building blocks has gained huge attention in the past decade. Compared with the modification of heterocyclic compounds, the construction of heterocyclic compounds from scratch is more attractive. In this Perspective, we describe our recent advances in the rational design and strategic application of the <i>de novo</i> synthesis of various synthetically and biologically important heterocycles. The organization of the Perspective is categorized in the following order: (a) type of heterocycle, (b) ring size of heterocycle, (c) number of heteroatoms, and (d) fused heterocycles. Moreover, some significant and representative synthetic methodologies and their synthetic applications and brief reaction mechanisms have also been described. We hope that this Perspective will help to provide a guideline for researchers who are interested in this fertile area.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":null,"pages":null},"PeriodicalIF":3.4,"publicationDate":"2024-07-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141602874","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}
引用次数: 0
Stereoselective Synthesis of ABBV-992 Enabled by a Flow Diazotization and a Partial Reduction of a Pyridone 通过流式重氮化和吡啶酮的部分还原实现 ABBV-992 的立体选择性合成
IF 3.4 3区 化学
Organic Process Research & Development Pub Date : 2024-07-12 DOI: 10.1021/acs.oprd.4c00077
Patrick B. Brady, Kaid C. Harper, Bryan K. Sorensen, Stephen N. Greszler, Chunqiu Lai, Alan S. Florjancic, Gang Zhao, Bhadra H. Shelat, Gregory E. Storer, Rodger F. Henry, T. Matthew Hansen
{"title":"Stereoselective Synthesis of ABBV-992 Enabled by a Flow Diazotization and a Partial Reduction of a Pyridone","authors":"Patrick B. Brady, Kaid C. Harper, Bryan K. Sorensen, Stephen N. Greszler, Chunqiu Lai, Alan S. Florjancic, Gang Zhao, Bhadra H. Shelat, Gregory E. Storer, Rodger F. Henry, T. Matthew Hansen","doi":"10.1021/acs.oprd.4c00077","DOIUrl":"https://doi.org/10.1021/acs.oprd.4c00077","url":null,"abstract":"Bruton’s tyrosine kinase (BTK) is involved in B-cell receptor signaling and has been clinically validated as a target by small molecule inhibition for the treatment of a variety of cancers. ABBV-992 (<b>1</b>) was identified as a novel, potent, selective BTK inhibitor and advanced to Phase I clinical trials. An enantioselective synthesis of <b>1</b> was developed and scaled to provide 63 g for preclinical characterization. The route features a diazotization enabled by flow chemistry, a novel, selective partial reduction of a pyridone, a stereoselective Ellman imine reduction, and an improved acrylamide formation using 3-chloropropionyl chloride in a masked acrylate strategy.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":null,"pages":null},"PeriodicalIF":3.4,"publicationDate":"2024-07-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141602876","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}
引用次数: 0
Autonomous Online Optimization in Flash Chemistry Using Online Mass Spectrometry 利用在线质谱仪实现闪蒸化学的自主在线优化
IF 3.4 3区 化学
Organic Process Research & Development Pub Date : 2024-07-12 DOI: 10.1021/acs.oprd.3c00397
Claudio Lehmann, Kevin Eckey, Maria Viehoff, Christoph Greve, Thorsten Röder
{"title":"Autonomous Online Optimization in Flash Chemistry Using Online Mass Spectrometry","authors":"Claudio Lehmann, Kevin Eckey, Maria Viehoff, Christoph Greve, Thorsten Röder","doi":"10.1021/acs.oprd.3c00397","DOIUrl":"https://doi.org/10.1021/acs.oprd.3c00397","url":null,"abstract":"The goal of sustainable and efficient chemical production has led to an increased focus on continuous processes, especially in the production of fine chemicals or active pharmaceutical ingredients. However, developing and optimizing continuous processes can be challenging. Autonomous online optimization can help facilitate this process. This article presents a fully automated flow chemistry platform for optimizing flash chemistry (reaction times less than 1 s), using online mass spectrometry and global optimization algorithms, such as Bayesian optimization and SNOBFIT, for autonomous online optimization of chemical reactions. The algorithms were tuned and statistically evaluated using simulated optimization runs. Subsequently, they were applied in a practical case study, using a mixing-sensitive example of flash chemistry as a model system to investigate online reaction optimization. Automated response factor fitting was used to obtain quantitative data directly during reaction monitoring. This approach allowed the extraction of meaningful data without the need for postprocessing. The use of an initial design of experiments (DoE) approach was advantageous as it provides a well-discovered experimental space and often leads to a minimal number of subsequent experiments for optimization. Although random starting points may require fewer total experiments, the DoE approach offers greater reliability in achieving optimal results. Comparative analysis between Bayesian optimization and SNOBFIT indicates that Bayesian optimization outperforms SNOBFIT, achieving better results with fewer experimental iterations. Thus, Bayesian optimization has proven to be a powerful tool for autonomous optimization of chemical processes.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":null,"pages":null},"PeriodicalIF":3.4,"publicationDate":"2024-07-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141602875","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}
引用次数: 0
Efficiency and Sustainability through Development of a Next-Generation, Commercial Synthesis of Valbenazine Ditosylate 通过开发新一代商业化缬氨嗪二对甲苯磺酸盐合成技术实现效率和可持续性
IF 3.4 3区 化学
Organic Process Research & Development Pub Date : 2024-07-12 DOI: 10.1021/acs.oprd.4c00148
John L. Tucker, David J. Kucera, Don Hettinger, Shawn Branum, Brian Cochran, Jeff Culhane, Lucy Zhao, Andrew Benjamin Palmer, Kyle Leeman, Stanley Yu, Bénédicte Martin, Nicolas André, Julien Perron, Horacio Comas, Yuxin Zhao
{"title":"Efficiency and Sustainability through Development of a Next-Generation, Commercial Synthesis of Valbenazine Ditosylate","authors":"John L. Tucker, David J. Kucera, Don Hettinger, Shawn Branum, Brian Cochran, Jeff Culhane, Lucy Zhao, Andrew Benjamin Palmer, Kyle Leeman, Stanley Yu, Bénédicte Martin, Nicolas André, Julien Perron, Horacio Comas, Yuxin Zhao","doi":"10.1021/acs.oprd.4c00148","DOIUrl":"https://doi.org/10.1021/acs.oprd.4c00148","url":null,"abstract":"The synthetic process used to manufacture valbenazine ditosylate (API of INGREZZA) has proven to be highly selective and robust, but opportunities remain for greener chemistry performance and continuous improvement enabled via simplification of process operations by truncating the manufacturing time and by reducing the overall process waste and environmental footprint during the first three most critical transformations. Neurocrine’s next-generation commercial process was developed encompassing principles of Pharmaceutical Green Chemistry ( <cite><i>Org. Process Res. Dev.</i></cite> <span>2006</span>, <em>10</em>, 315−319) and employs strategies for accelerated reaction kinetics, simplified reaction medium, and elimination of unnecessary workup procedures for greater process efficiency and operational agility. The new, greener process has delivered greater efficiency and sustainability by reducing the time of manufacture by 43% and reducing material use by 45% while concomitantly improving the overall process yield by 5% and reducing water use by 32%.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":null,"pages":null},"PeriodicalIF":3.4,"publicationDate":"2024-07-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141602877","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}
引用次数: 0
Going with the Flow: Implementation of a New Continuous Process for a Selective Acetal Deprotection 顺其自然:实施选择性乙缩醛脱保护的新型连续工艺
IF 3.4 3区 化学
Organic Process Research & Development Pub Date : 2024-07-11 DOI: 10.1021/acs.oprd.3c00401
Adam Clarke, Heena Panchal, Jigang Yang, Yunfeng Bai, Yuedong Wu, Jinxu Sun, Zhiyuan Zhou
{"title":"Going with the Flow: Implementation of a New Continuous Process for a Selective Acetal Deprotection","authors":"Adam Clarke, Heena Panchal, Jigang Yang, Yunfeng Bai, Yuedong Wu, Jinxu Sun, Zhiyuan Zhou","doi":"10.1021/acs.oprd.3c00401","DOIUrl":"https://doi.org/10.1021/acs.oprd.3c00401","url":null,"abstract":"DB Mesylate is a common intermediate used in the production of cEt amidites, supporting part of AstraZeneca’s oligonucleotide portfolio. The current process to manufacture DB Mesylate includes eight stages with three isolated intermediates and is well understood. This paper covers the implementation of a flow process to resolve the throughput, yield, and manufacturing challenges associated with the key acetal deprotection stage.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":null,"pages":null},"PeriodicalIF":3.4,"publicationDate":"2024-07-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141588839","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}
引用次数: 0
Application of Imine Reductase in Bioactive Chiral Amine Synthesis 亚胺还原酶在生物活性手性胺合成中的应用
IF 3.4 3区 化学
Organic Process Research & Development Pub Date : 2024-07-11 DOI: 10.1021/acs.oprd.4c00147
Zhi Wang, Guang-Sheng Gao, Ya-Dong Gao, Li-Cheng Yang
{"title":"Application of Imine Reductase in Bioactive Chiral Amine Synthesis","authors":"Zhi Wang, Guang-Sheng Gao, Ya-Dong Gao, Li-Cheng Yang","doi":"10.1021/acs.oprd.4c00147","DOIUrl":"https://doi.org/10.1021/acs.oprd.4c00147","url":null,"abstract":"Nitrogen-containing compounds, especially those with chiral amine structures, play a pivotal role in the field of organic active pharmaceutical ingredients. Traditional racemate resolution and chemical synthesis methods for the preparation of chiral amines suffer drawbacks such as high cost and environmental pollution. Over the past decades, stereoselective synthesis of nitrogen-containing compounds by biocatalytic methods such as imine reductase (IRED)-mediated transformation has become increasingly prominent. The prominence of imine reductases lies in their capacity to catalyze the reductive amination of aldehydes or ketones with primary or secondary amines, as well as their broader substrate scope. Furthermore, imine reductases exhibit diverse catalytic cycling systems that are unaffected by adverse reaction equilibria. This article focuses on the development of drug molecules or intermediates in biocatalytic synthesis mediated by imine reductase.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":null,"pages":null},"PeriodicalIF":3.4,"publicationDate":"2024-07-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141588840","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}
引用次数: 0
Process Development of Bersacapavir, Part 2. Early Game Route Selection: Catalytic versus Stoichiometric Haloform-Type Amidation Bersacapavir 的工艺开发,第 2 部分。早期游戏路线选择:催化卤代甲酰胺化与计量卤代甲酰胺化的比较
IF 3.4 3区 化学
Organic Process Research & Development Pub Date : 2024-07-10 DOI: 10.1021/acs.oprd.4c00154
Florian Medina, William M. Maton, Jean-Pierre Bongartz, David Kossler, Magnus Eriksson, Johan Weerts, Micha Peeters, Koen Wegsteen, Els Keppens
{"title":"Process Development of Bersacapavir, Part 2. Early Game Route Selection: Catalytic versus Stoichiometric Haloform-Type Amidation","authors":"Florian Medina, William M. Maton, Jean-Pierre Bongartz, David Kossler, Magnus Eriksson, Johan Weerts, Micha Peeters, Koen Wegsteen, Els Keppens","doi":"10.1021/acs.oprd.4c00154","DOIUrl":"https://doi.org/10.1021/acs.oprd.4c00154","url":null,"abstract":"During the chemical development of bersacapavir API, special attention was paid to the key step of the early game synthesis: the extended haloform-type amidation. This manuscript describes the effort of the team toward the development of a catalytic version of that transformation thanks to the use of 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) and its unique reactivity. Guided by fine solubility studies, the catalytic procedure was optimized, streamlined, and scaled up. A very high yield and purity were achieved with significant process mass intensity (PMI) improvement in comparison to the previous process utilizing an excess of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU).","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":null,"pages":null},"PeriodicalIF":3.4,"publicationDate":"2024-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141588841","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}
引用次数: 0
Optimization for the Preparation of Procyanidin B3: Strategy for Gram-Scale and Stereoselective Formation of 4,8-Interflavan Bonds 优化原花青素 B3 的制备:4,8-间黄烷键的革兰氏级立体选择性形成策略
IF 3.4 3区 化学
Organic Process Research & Development Pub Date : 2024-07-10 DOI: 10.1021/acs.oprd.4c00271
Heyanhao Zhang, Jintao He, Rongqian Cheng, Huanren Yan, Mei-Lin Tang, Jun Chang
{"title":"Optimization for the Preparation of Procyanidin B3: Strategy for Gram-Scale and Stereoselective Formation of 4,8-Interflavan Bonds","authors":"Heyanhao Zhang, Jintao He, Rongqian Cheng, Huanren Yan, Mei-Lin Tang, Jun Chang","doi":"10.1021/acs.oprd.4c00271","DOIUrl":"https://doi.org/10.1021/acs.oprd.4c00271","url":null,"abstract":"Oligomeric proanthocyanidins (OPCs) have a variety of biological functions, but the formation of 4,8-interflavan bonds faces scaling-up difficulties due to the challenging control of stereoselectivity and the degree of polymerization. Here we report a process to produce procyanidin B3 (<b>1</b>) by mainly optimizing the condensation reaction and improving benzylation, C4 activation, and one-pot hydrogenolysis reactions. In an optimized seven-step process, the product <b>1</b> was achieved by only one-step chromatography in the case of poor crystallinity of polyphenols. This strategy provided effective access to the stereoselective synthesis of the title compound and other C4–C8 connected OPCs.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":null,"pages":null},"PeriodicalIF":3.4,"publicationDate":"2024-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141588842","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}
引用次数: 0
Automated Continuous Crystallization Platform with Real-Time Particle Size Analysis via Laser Diffraction 通过激光衍射进行实时粒度分析的自动化连续结晶平台
IF 3.4 3区 化学
Organic Process Research & Development Pub Date : 2024-07-09 DOI: 10.1021/acs.oprd.4c00110
Sayan Pal, Arun Pankajakshan, Maximilian O. Besenhard, Nicholas Snead, Juan Almeida, Shorooq Abukhamees, Duncan Craig, Federico Galvanin, Asterios Gavriilidis, Luca Mazzei
{"title":"Automated Continuous Crystallization Platform with Real-Time Particle Size Analysis via Laser Diffraction","authors":"Sayan Pal, Arun Pankajakshan, Maximilian O. Besenhard, Nicholas Snead, Juan Almeida, Shorooq Abukhamees, Duncan Craig, Federico Galvanin, Asterios Gavriilidis, Luca Mazzei","doi":"10.1021/acs.oprd.4c00110","DOIUrl":"https://doi.org/10.1021/acs.oprd.4c00110","url":null,"abstract":"The fourth industrial revolution is gaining momentum in the pharmaceutical industry. However, particulate processes and suspension handling remain big challenges for automation and the implementation of real-time particle size analysis. Moreover, the development of antisolvent crystallization processes is often limited by the associated time-intensive experimental screenings. This work demonstrates a fully automated modular crystallization platform that overcomes these bottlenecks. The system combines automated crystallization, sample preparation, and immediate crystal size analysis via online laser diffraction (LD) and provides a technology for rapidly screening crystallization process parameters and crystallizer design spaces with minimal experimental effort. During the LD measurements, to avoid multiple scattering events, crystal suspension samples are diluted automatically. Multiple software tools, i.e., LabVIEW, Python, and PharmaMV, and logic algorithms are integrated in the platform to facilitate automated control of all the sensors and equipment, enabling fully automated operation. A customized graphical user interface is provided to operate the crystallization platform automatically and to visualize the measured crystal size and the crystal size distribution of the suspension. Antisolvent crystallization of ibuprofen, with ethanol as solvent and water with Soluplus (an additive) as antisolvent, is used as a case study. The platform is demonstrated for antisolvent crystallization of small ibuprofen crystals in a confined impinging jet crystallizer, performing automated preplanned user-defined experiments with online LD analysis.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":null,"pages":null},"PeriodicalIF":3.4,"publicationDate":"2024-07-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141561802","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}
引用次数: 0
Deoxyfluorination of Ketones with Sulfur Tetrafluoride (SF4) and Dialkylamines in Continuous Flow Mode 用四氟化硫 (SF4) 和二烷基胺在连续流模式下对酮进行脱氧氟化反应
IF 3.4 3区 化学
Organic Process Research & Development Pub Date : 2024-07-08 DOI: 10.1021/acs.oprd.4c00180
Dominik Polterauer, Simon Wagschal, Michael Bersier, Clara Bovino, Dominique M. Roberge, Christopher A. Hone, C. Oliver Kappe
{"title":"Deoxyfluorination of Ketones with Sulfur Tetrafluoride (SF4) and Dialkylamines in Continuous Flow Mode","authors":"Dominik Polterauer, Simon Wagschal, Michael Bersier, Clara Bovino, Dominique M. Roberge, Christopher A. Hone, C. Oliver Kappe","doi":"10.1021/acs.oprd.4c00180","DOIUrl":"https://doi.org/10.1021/acs.oprd.4c00180","url":null,"abstract":"Fluorinated molecules are prevalent in biologically active substances, in particular, the <i>gem</i>-difluoro motif. However, the selective incorporation of a <i>gem</i>-difluoro motif into organic molecules is a laborious task. Deoxyfluorination is a promising and widely used methodology to achieve this transformation, which is usually costly or highly hazardous. Herein, we report a deoxyfluorination protocol using sulfur tetrafluoride (SF<sub>4</sub>) and diethylamine (Et<sub>2</sub>NH) to prepare <i>gem-</i>difluorides in continuous flow mode. The process does not require the addition of exogenous HF, and <i>in situ</i> generated reagents were quenched in-line, which improved safety. The methodology was successfully applied to convert a broad range of 4-, 5-, and 6-membered ketone derivatives to their corresponding difluorinated compounds while minimizing the undesired vinyl fluoride formation. In summary, these findings improve safety and selectivity toward the synthesis of <i>gem</i>-difluoro compounds drastically, enabling a more efficient production of fluorinated active pharmaceutical ingredients.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":null,"pages":null},"PeriodicalIF":3.4,"publicationDate":"2024-07-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141561803","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}
引用次数: 0
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