Organic Process Research & Development最新文献_第5页

Soft and Sustainable Synthesis of Perylene Diimides through Soluble Surrogates of Perylenetetracarboxylic Acid Dianhydride 用可溶的苝四羧酸二酐代物软性可持续合成苝二酰亚胺

IF 3.4 3区化学

Organic Process Research & Development Pub Date : 2025-04-22 DOI: 10.1021/acs.oprd.5c00063

Rubén Cruz-Sánchez, Antonio Peñas-Sanjuán, José J. Chica-Armenteros, M. Luz Godino-Salido, Celeste García-Gallarín, Manuel Melguizo

{"title":"Soft and Sustainable Synthesis of Perylene Diimides through Soluble Surrogates of Perylenetetracarboxylic Acid Dianhydride","authors":"Rubén Cruz-Sánchez, Antonio Peñas-Sanjuán, José J. Chica-Armenteros, M. Luz Godino-Salido, Celeste García-Gallarín, Manuel Melguizo","doi":"10.1021/acs.oprd.5c00063","DOIUrl":"https://doi.org/10.1021/acs.oprd.5c00063","url":null,"abstract":"An unprecedented strategy for the efficient and direct synthesis of perylene-3,4,9,10-tetracarboxylic diimides (PDIs) through a well-defined and controlled reaction mechanism has been developed. The procedure is based on the opening of the anhydride groups of perylene-3,4,9,10-tetracarboxylic dianhydride (PDA) as nonplanar diester-type perylene-3,4,9,10-tetracarboxylic acid (MESAC), which act as highly soluble surrogates of PDA that enable the preparation of PDIs under soft conditions compatible with thermolabile groups. A ready interconversion, in amine methanolic solution, between the cyclic anhydride groups of PDA and the groupings resulting from their methanolysis (methyl esters+ammonium carboxylate) and aminolysis (amide+ammonium carboxylate) was studied, and the presence of postulated (nonisolated) intermediates was detected by UV–vis and HPLC/HRMS. The intermediates originated by double aminolysis with primary amines of both anhydride groups of PDA render diamide-type perylene-3,4,9,10-tetracarboxylic acid (s-AMAC) intermediates whose selective cyclization to yield PDIs required basic media, while acidic media produce reversion to the anhydride (PDA). The procedure emerging from these studies provides a robust methodology with a wide scope for the synthesis of PDIs under soft and environmentally friendly conditions.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"37 1","pages":""},"PeriodicalIF":3.4,"publicationDate":"2025-04-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143858120","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

Valorization of Pharmaceutical Waste by Recovery of Active Pharmaceutical Ingredients from Expired or Unused Finished Pharmaceutical Products with Thermodynamic Modeling 利用热力学模型从过期或未使用的制成品中回收有效药物成分使药物废物增值

IF 3.4 3区化学

Organic Process Research & Development Pub Date : 2025-04-22 DOI: 10.1021/acs.oprd.5c00093

Jaber Yousefi Seyf, Fatemeh Zarei, Amir Jalalinejad

{"title":"Valorization of Pharmaceutical Waste by Recovery of Active Pharmaceutical Ingredients from Expired or Unused Finished Pharmaceutical Products with Thermodynamic Modeling","authors":"Jaber Yousefi Seyf, Fatemeh Zarei, Amir Jalalinejad","doi":"10.1021/acs.oprd.5c00093","DOIUrl":"https://doi.org/10.1021/acs.oprd.5c00093","url":null,"abstract":"This study aims to investigate the possibility of recovering active pharmaceutical ingredients (APIs) from expired or unused finished pharmaceutical products (FPPs). Five pharmaceuticals, including ibuprofen, acetaminophen, lamotrigine, phenobarbital, and carbamazepine, were chosen as FPP models. At the beginning of the study, thermodynamic modeling of pharmaceutical solubility was done by the NRTL-SAC and UNIFAC-DMD activity coefficient models in order to screen the 62 approved solvents as determined by the Food and Drug Administration. These models reduce the time and cost associated with the experimental tries. Solid–liquid extraction, filtration, and crystallization are the three main unit operations that are used to purify pharmaceuticals. Results showed that the efficiency of the active pharmaceutical ingredient recovery is between 47 and 81%, mainly above 50%. Also, the purity of the recovered APIs, as the most important factor, was analyzed using melting point FT-IR, UV, high-performance liquid chromatography, and 1H NMR techniques. Results show that the purity obtained for most recovered APIs is near 100%. So, the purified APIs can be reused in formulation by finished product companies or as starting material in synthesizing derivatives in organic chemistry to obtain new molecules. The present research met the green chemistry criteria and shows significant importance from environmental and economic points of view.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"71 1","pages":""},"PeriodicalIF":3.4,"publicationDate":"2025-04-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143862653","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

Continuous Flow for the Photochemical Synthesis of 3-Substituted Quinolines 3-取代喹啉类化合物光化学合成的连续流程研究

IF 3.1 3区化学

Organic Process Research & Development Pub Date : 2025-04-22 DOI: 10.1021/acs.oprd.4c0053410.1021/acs.oprd.4c00534

Márk Molnár, Tamás Fődi, János Tatai, Vilibald Kun, Barbara Balázs, Tamás Gáti, Gergő Dargó and Miklós Nyerges*,

引用次数: 0

Valorization of Pharmaceutical Waste by Recovery of Active Pharmaceutical Ingredients from Expired or Unused Finished Pharmaceutical Products with Thermodynamic Modeling 利用热力学模型从过期或未使用的制成品中回收有效药物成分使药物废物增值

IF 3.1 3区化学

Organic Process Research & Development Pub Date : 2025-04-22 DOI: 10.1021/acs.oprd.5c0009310.1021/acs.oprd.5c00093

Jaber Yousefi Seyf*, Fatemeh Zarei and Amir Jalalinejad,

{"title":"Valorization of Pharmaceutical Waste by Recovery of Active Pharmaceutical Ingredients from Expired or Unused Finished Pharmaceutical Products with Thermodynamic Modeling","authors":"Jaber Yousefi Seyf*, Fatemeh Zarei and Amir Jalalinejad, ","doi":"10.1021/acs.oprd.5c0009310.1021/acs.oprd.5c00093","DOIUrl":"https://doi.org/10.1021/acs.oprd.5c00093https://doi.org/10.1021/acs.oprd.5c00093","url":null,"abstract":"This study aims to investigate the possibility of recovering active pharmaceutical ingredients (APIs) from expired or unused finished pharmaceutical products (FPPs). Five pharmaceuticals, including ibuprofen, acetaminophen, lamotrigine, phenobarbital, and carbamazepine, were chosen as FPP models. At the beginning of the study, thermodynamic modeling of pharmaceutical solubility was done by the NRTL-SAC and UNIFAC-DMD activity coefficient models in order to screen the 62 approved solvents as determined by the Food and Drug Administration. These models reduce the time and cost associated with the experimental tries. Solid–liquid extraction, filtration, and crystallization are the three main unit operations that are used to purify pharmaceuticals. Results showed that the efficiency of the active pharmaceutical ingredient recovery is between 47 and 81%, mainly above 50%. Also, the purity of the recovered APIs, as the most important factor, was analyzed using melting point FT-IR, UV, high-performance liquid chromatography, and 1H NMR techniques. Results show that the purity obtained for most recovered APIs is near 100%. So, the purified APIs can be reused in formulation by finished product companies or as starting material in synthesizing derivatives in organic chemistry to obtain new molecules. The present research met the green chemistry criteria and shows significant importance from environmental and economic points of view.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"29 5","pages":"1333–1344 1333–1344"},"PeriodicalIF":3.1,"publicationDate":"2025-04-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144067818","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

Enantioselective Synthesis of Savolitinib: Application of Mosher’s Method in the Development of Ellman’s Auxiliary-Directed Construction of the Key Chiral Amine Fragment 萨伏替尼的对映选择性合成：Mosher法在Ellman辅助定向构建关键手性胺片段中的应用

IF 3.4 3区化学

Organic Process Research & Development Pub Date : 2025-04-21 DOI: 10.1021/acs.oprd.4c00446

Saikat Sen, Vishnuvardhan Reddy Eda, Magesh Sampath, Karthik Pulluri, Shirshendu Das Gupta, Rajeev Rehani Budhdev, Rakeshwar Bandichhor, Srinivas Oruganti

引用次数: 0

Enantioselective Synthesis of Savolitinib: Application of Mosher’s Method in the Development of Ellman’s Auxiliary-Directed Construction of the Key Chiral Amine Fragment 萨伏替尼的对映选择性合成：Mosher法在Ellman辅助定向构建关键手性胺片段中的应用

IF 3.1 3区化学

Organic Process Research & Development Pub Date : 2025-04-21 DOI: 10.1021/acs.oprd.4c0044610.1021/acs.oprd.4c00446

Saikat Sen*, Vishnuvardhan Reddy Eda, Magesh Sampath, Karthik Pulluri, Shirshendu Das Gupta, Rajeev Rehani Budhdev, Rakeshwar Bandichhor and Srinivas Oruganti*,

{"title":"Enantioselective Synthesis of Savolitinib: Application of Mosher’s Method in the Development of Ellman’s Auxiliary-Directed Construction of the Key Chiral Amine Fragment","authors":"Saikat Sen*, Vishnuvardhan Reddy Eda, Magesh Sampath, Karthik Pulluri, Shirshendu Das Gupta, Rajeev Rehani Budhdev, Rakeshwar Bandichhor and Srinivas Oruganti*, ","doi":"10.1021/acs.oprd.4c0044610.1021/acs.oprd.4c00446","DOIUrl":"https://doi.org/10.1021/acs.oprd.4c00446https://doi.org/10.1021/acs.oprd.4c00446","url":null,"abstract":"An efficient rational synthesis of (S)-1-(imidazo[1,2-a]pyridin-6-yl)ethan-1-amine via Ellman’s auxiliary approach and elaboration of this key chiral intermediate into the anticancer drug Savolitinib has been described. An apt combination of Ellman’s sulfinamide and reducing agent afforded high levels of diastereofacial control during hydride addition and secured the desired S configuration in the intermediate, which was unambiguously verified by application of Mosher’s amide method. Our nine-step synthetic sequence to Savolitinib commences with commercially available 6-amino-nicotinic acid and was first demonstrated as a proof-of-concept study on a lab scale. It was then refined during scale-up to allow telescoping of six stages and afford the final API Savolitinib with >99% chiral purity.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"29 5","pages":"1218–1227 1218–1227"},"PeriodicalIF":3.1,"publicationDate":"2025-04-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144067779","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

Continuous Flow Synthesis and Kinetic Study of Diphenyl Sulfoxide in a Microreactor 微反应器中二苯基亚砜的连续流动合成及动力学研究

IF 3.4 3区化学

Organic Process Research & Development Pub Date : 2025-04-16 DOI: 10.1021/acs.oprd.5c00018

Hongrui Zhang, Feng Xu, Xiang Zhou, Zhiquan Chen, Juncheng Jiang, Gang Fu, Lei Ni

{"title":"Continuous Flow Synthesis and Kinetic Study of Diphenyl Sulfoxide in a Microreactor","authors":"Hongrui Zhang, Feng Xu, Xiang Zhou, Zhiquan Chen, Juncheng Jiang, Gang Fu, Lei Ni","doi":"10.1021/acs.oprd.5c00018","DOIUrl":"https://doi.org/10.1021/acs.oprd.5c00018","url":null,"abstract":"The oxidation of diphenyl sulfide (DPS) by hydrogen peroxide (H2O2) to synthesize diphenyl sulfoxide (DPSO) is extremely exothermic and has a high thermal risk. When thermal runaway happens, it may lead to equipment damage or even explosions. Therefore, in this work, a microreactor was adopted to reduce reaction thermal risk and process conditions were optimized. Phosphotungstic acid (PTA) was used as the catalyst, and the effects of process conditions, including reaction temperature, residence time, catalyst concentration, and molar ratio on the conversion and yield were systematically investigated. The results showed that the DPSO yield could reach up to 84.3% under the condition of 0.75% catalyst loading, 25 min residence time, 70 °C reaction temperature, and H2O2–DPS molar ratio of 2. Then, apparent reaction kinetics were studied, and a kinetic model was established and validated. By varying the initial concentrations of H2O2 and DPS, the reaction was determined to be of second-order, with an activation energy of 57.5 kJ·mol–1 and a pre-exponential factor of 2.96 × 107 mol–1·L·min–1. Furthermore, the temperature distribution along the microreactor was estimated by combining the thermal equilibrium with the reaction kinetics. The results indicated that in a 1/16 in. microreactor, the reaction was nearly isothermal. Temperature distributions were also predicted for microreactors with different diameters and materials. It was demonstrated that the reaction could be safely scaled up to a 3/8 in. microreactor at a reaction temperature of 55 °C, with the maximum temperature rise remaining below 5 °C and no decline in DPSO yield. This study provided a convenient method to guide the safe sizing-up of the reaction in flow reactors.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"74 1","pages":""},"PeriodicalIF":3.4,"publicationDate":"2025-04-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143836950","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

Continuous Flow Synthesis and Kinetic Study of Diphenyl Sulfoxide in a Microreactor 微反应器中二苯基亚砜的连续流动合成及动力学研究

IF 3.1 3区化学

Organic Process Research & Development Pub Date : 2025-04-16 DOI: 10.1021/acs.oprd.5c0001810.1021/acs.oprd.5c00018

Hongrui Zhang, Feng Xu, Xiang Zhou, Zhiquan Chen, Juncheng Jiang, Gang Fu* and Lei Ni*,

{"title":"Continuous Flow Synthesis and Kinetic Study of Diphenyl Sulfoxide in a Microreactor","authors":"Hongrui Zhang, Feng Xu, Xiang Zhou, Zhiquan Chen, Juncheng Jiang, Gang Fu* and Lei Ni*, ","doi":"10.1021/acs.oprd.5c0001810.1021/acs.oprd.5c00018","DOIUrl":"https://doi.org/10.1021/acs.oprd.5c00018https://doi.org/10.1021/acs.oprd.5c00018","url":null,"abstract":"The oxidation of diphenyl sulfide (DPS) by hydrogen peroxide (H2O2) to synthesize diphenyl sulfoxide (DPSO) is extremely exothermic and has a high thermal risk. When thermal runaway happens, it may lead to equipment damage or even explosions. Therefore, in this work, a microreactor was adopted to reduce reaction thermal risk and process conditions were optimized. Phosphotungstic acid (PTA) was used as the catalyst, and the effects of process conditions, including reaction temperature, residence time, catalyst concentration, and molar ratio on the conversion and yield were systematically investigated. The results showed that the DPSO yield could reach up to 84.3% under the condition of 0.75% catalyst loading, 25 min residence time, 70 °C reaction temperature, and H2O2–DPS molar ratio of 2. Then, apparent reaction kinetics were studied, and a kinetic model was established and validated. By varying the initial concentrations of H2O2 and DPS, the reaction was determined to be of second-order, with an activation energy of 57.5 kJ·mol–1 and a pre-exponential factor of 2.96 × 107 mol–1·L·min–1. Furthermore, the temperature distribution along the microreactor was estimated by combining the thermal equilibrium with the reaction kinetics. The results indicated that in a 1/16 in. microreactor, the reaction was nearly isothermal. Temperature distributions were also predicted for microreactors with different diameters and materials. It was demonstrated that the reaction could be safely scaled up to a 3/8 in. microreactor at a reaction temperature of 55 °C, with the maximum temperature rise remaining below 5 °C and no decline in DPSO yield. This study provided a convenient method to guide the safe sizing-up of the reaction in flow reactors.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"29 5","pages":"1279–1290 1279–1290"},"PeriodicalIF":3.1,"publicationDate":"2025-04-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144067738","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

Access to Phenolic Pyridopyridazinones and Phthalazinones Using THP Ether-Directed Ortho Lithiation 利用 THP 乙醚定向正锂化技术获得酚类哒嗪酮和酞嗪酮

IF 3.4 3区化学

Organic Process Research & Development Pub Date : 2025-04-15 DOI: 10.1021/acs.oprd.4c00541

Helena Leuser, Subhash Pithani, Staffan Karlsson, Carl-Johan Aurell, Marcus Malmgren, Per-Ola Norrby, Okky D. Putra

{"title":"Access to Phenolic Pyridopyridazinones and Phthalazinones Using THP Ether-Directed Ortho Lithiation","authors":"Helena Leuser, Subhash Pithani, Staffan Karlsson, Carl-Johan Aurell, Marcus Malmgren, Per-Ola Norrby, Okky D. Putra","doi":"10.1021/acs.oprd.4c00541","DOIUrl":"https://doi.org/10.1021/acs.oprd.4c00541","url":null,"abstract":"Route scouting, process research and development, and large-scale synthesis of phenol-substituted pyridopyridazinones (azaphthalazinones) and phthalazinones are reported. For the introduction of one of our key building blocks, 3-(trifluoromethyl)phenol, our identified large-scale route initially employed an unstable aryllithium, generated by bromine lithium exchange next to a phenolic hydroxy group protected as p-methoxybenzyl (PMB) ether. We found that instead, protecting the phenolic hydroxy group as tetrahydropyran (THP) ether in a bromine-free substrate and applying directed ortho metalation (DoM) generated the desired aryllithium in a stable form, suitable for use in a batch process on a large scale, which significantly facilitated the synthesis of our target molecules. The final process, a palladium-free, telescoped two-step sequence consisting of ketone formation by acylation with a mixed diester and cyclization with hydrazine, was demonstrated in our kilogram laboratory on a 0.5 kg scale for the pyridopyridazinone scaffold. Routes to the analogous phthalazinone scaffold were also investigated, and here, both phthalic anhydride and a mixed diester can serve as starting material. DFT calculations support our rationale regarding experimentally found differences between pyridine- and benzene-based intermediates. The target molecules were isolated as crystalline solids, and their structures were further confirmed by single crystal X-ray diffraction.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"284 1","pages":""},"PeriodicalIF":3.4,"publicationDate":"2025-04-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143832495","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

Access to Phenolic Pyridopyridazinones and Phthalazinones Using THP Ether-Directed Ortho Lithiation 利用THP醚定向邻位锂化法获得酚醛吡啶吡啶酮和酞嗪酮

IF 3.1 3区化学

Organic Process Research & Development Pub Date : 2025-04-15 DOI: 10.1021/acs.oprd.4c0054110.1021/acs.oprd.4c00541

Helena Leuser*, Subhash Pithani, Staffan Karlsson, Carl-Johan Aurell, Marcus Malmgren, Per-Ola Norrby and Okky D. Putra,

{"title":"Access to Phenolic Pyridopyridazinones and Phthalazinones Using THP Ether-Directed Ortho Lithiation","authors":"Helena Leuser*, Subhash Pithani, Staffan Karlsson, Carl-Johan Aurell, Marcus Malmgren, Per-Ola Norrby and Okky D. Putra, ","doi":"10.1021/acs.oprd.4c0054110.1021/acs.oprd.4c00541","DOIUrl":"https://doi.org/10.1021/acs.oprd.4c00541https://doi.org/10.1021/acs.oprd.4c00541","url":null,"abstract":"Route scouting, process research and development, and large-scale synthesis of phenol-substituted pyridopyridazinones (azaphthalazinones) and phthalazinones are reported. For the introduction of one of our key building blocks, 3-(trifluoromethyl)phenol, our identified large-scale route initially employed an unstable aryllithium, generated by bromine lithium exchange next to a phenolic hydroxy group protected as p-methoxybenzyl (PMB) ether. We found that instead, protecting the phenolic hydroxy group as tetrahydropyran (THP) ether in a bromine-free substrate and applying directed ortho metalation (DoM) generated the desired aryllithium in a stable form, suitable for use in a batch process on a large scale, which significantly facilitated the synthesis of our target molecules. The final process, a palladium-free, telescoped two-step sequence consisting of ketone formation by acylation with a mixed diester and cyclization with hydrazine, was demonstrated in our kilogram laboratory on a 0.5 kg scale for the pyridopyridazinone scaffold. Routes to the analogous phthalazinone scaffold were also investigated, and here, both phthalic anhydride and a mixed diester can serve as starting material. DFT calculations support our rationale regarding experimentally found differences between pyridine- and benzene-based intermediates. The target molecules were isolated as crystalline solids, and their structures were further confirmed by single crystal X-ray diffraction.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"29 5","pages":"1248–1263 1248–1263"},"PeriodicalIF":3.1,"publicationDate":"2025-04-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144067708","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