Organic Process Research & Development最新文献_第4页

Process Development of a PI3Kδ Inhibitor: A Novel and Practical [1,2]-Boc Migration on Purine Rings PI3Kδ抑制剂的工艺开发：一种新颖实用的[1,2]-Boc在嘌呤环上的迁移

IF 3.5 3区化学

Organic Process Research & Development Pub Date : 2025-08-14 DOI: 10.1021/acs.oprd.5c00272

Tsuyoshi Ueda*, Kei Kurahashi, Yoshio Nishi and Yutaka Kitagawa,

{"title":"Process Development of a PI3Kδ Inhibitor: A Novel and Practical [1,2]-Boc Migration on Purine Rings","authors":"Tsuyoshi Ueda*, Kei Kurahashi, Yoshio Nishi and Yutaka Kitagawa, ","doi":"10.1021/acs.oprd.5c00272","DOIUrl":"https://doi.org/10.1021/acs.oprd.5c00272","url":null,"abstract":"This study describes the process development for the synthesis of a phosphoinositide 3-kinase (PI3K) δ selective inhibitor 1. The most important challenge was to establish the optimal method for introducing the carbonyl group at the 8-position, which posed the greatest difficulties in the medicinal chemistry (Med-Chem) method, and to determine the most suitable timing for this step in the manufacturing process. To address the challenges encountered with the Med-Chem method, three alternative synthetic routes were explored, focusing especially on functionalization of the 8-position, a key transformation in the process. During this route exploration, we developed a novel, practical, and high-yield [1,2]-Boc migration reaction. In the final selected route, after introducing the morpholine group at the 6-position, the 9-position was protected by Boc. Subsequently, employing lithium bis(trimethylsilyl)amide (LHMDS) facilitated our [1,2]-Boc migration reaction, which successfully produced the desired t-butyl ester at the 8-position in high yield. Subsequent steps involved Suzuki coupling to introduce the pyrazole part, hydrolysis of the t-butyl ester, amidation, and final recrystallization, ultimately yielding PI3Kδ inhibitor 1 with excellent yield. Over 7 steps, including the final recrystallization, the overall yield of 69% was achieved, representing a significant improvement over the Med-Chem approach.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"29 9","pages":"2429–2442"},"PeriodicalIF":3.5,"publicationDate":"2025-08-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145094372","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

Control Strategies for Mitigating Ritter and Methyl Ester Impurities in Mezigdomide Manufacturing 减少美西多胺生产中残渣和甲酯杂质的控制策略

IF 3.5 3区化学

Organic Process Research & Development Pub Date : 2025-08-14 DOI: 10.1021/acs.oprd.5c00202

Jennifer Lott*, Geoffrey E. Purdum, Antonio C. Ferretti, Antonio Ramirez, Qinggang Wang, Gerald D. Artman III, Scott J. Bader, Michaela Marquez, Brian Marquez and Hon-Wah Man,

{"title":"Control Strategies for Mitigating Ritter and Methyl Ester Impurities in Mezigdomide Manufacturing","authors":"Jennifer Lott*, Geoffrey E. Purdum, Antonio C. Ferretti, Antonio Ramirez, Qinggang Wang, Gerald D. Artman III, Scott J. Bader, Michaela Marquez, Brian Marquez and Hon-Wah Man, ","doi":"10.1021/acs.oprd.5c00202","DOIUrl":"https://doi.org/10.1021/acs.oprd.5c00202","url":null,"abstract":"During a tert-butyl ester deprotection/imide cyclization sequence designed to form the glutarimide ring of Mezigdomide (CC-92480), side reactions were observed. In particular, the N-(tert-butyl)benzamide impurity, formed by the Ritter reaction between the tert-butyl cation and the aryl nitrile, was observed at high and variable levels during early development and did not purge sufficiently to meet product specifications. Reaction engineering efforts were undertaken to optimize the process, minimize this challenging Ritter impurity, and avoid the need for extensive downstream purifications. Kinetic profiling revealed that the Ritter reaction involving the acetonitrile solvent could be leveraged to deplete the tert-butyl cation concentration. Combining nitrogen sparging (to remove isobutylene from the gas phase) and dilution provided a scalable control strategy for this impurity. A kinetic model was developed to accurately predict impurity levels, although some outliers could not be explained. Further investigations revealed an unrelated, coeluting methyl ester impurity, caused by residual methanol used as a cleaning solvent. A second control strategy was developed for the methyl ester impurity, leveraging fate and purge experiments, robust analytical methods, and most importantly, a comprehensive cleaning protocol for manufacturing. Combining these two control strategies, the optimized process provided excellent control of both impurities and was scaled up to enable the production of highly pure Mezigdomide.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"29 9","pages":"2310–2320"},"PeriodicalIF":3.5,"publicationDate":"2025-08-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145094404","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 of a Parham Cyclization Aided by In Situ FTIR for an Enabling Synthesis of Tricyclo[6.2.0.03,6]deca-1,3(6),7-trien-2-amine [6.2.0.03,6]三环-1,3(6)，7- 3 -2-胺的原位FTIR辅助Parham环化优化

IF 3.5 3区化学

Organic Process Research & Development Pub Date : 2025-08-12 DOI: 10.1021/acs.oprd.5c00181

Janis Jermaks*, Haiming Zhang, Thomas C. Malig, Ngiap-Kie Lim, Johannes A. Burkhard, Chong Han and Francis Gosselin,

{"title":"Optimization of a Parham Cyclization Aided by In Situ FTIR for an Enabling Synthesis of Tricyclo[6.2.0.03,6]deca-1,3(6),7-trien-2-amine","authors":"Janis Jermaks*, Haiming Zhang, Thomas C. Malig, Ngiap-Kie Lim, Johannes A. Burkhard, Chong Han and Francis Gosselin, ","doi":"10.1021/acs.oprd.5c00181","DOIUrl":"https://doi.org/10.1021/acs.oprd.5c00181","url":null,"abstract":"An enabling synthesis of tricyclo[6.2.0.03,6]deca-1,3(6),7-trien-2-amine was developed starting from p-phenylenediacetic acid. The readily available p-phenylenediacetic acid was first converted in four steps to 1,4-dibromo-2,5-bis(2-bromoethyl)benzene, which was then subjected to Parham cyclization conditions. The mechanistic analysis of the Parham cyclization revealed that controlling the temperature and solvent environment was crucial. Process analytical technology (PAT) was used in the optimization of this intramolecular cyclization to identify the optimal temperature range for the halogen–metal exchange and intramolecular cyclization steps by means of a single kinetic experiment with increasing temperatures. A set of these small-scale experiments were conducted to fine-tune the reaction parameters and ensure scalability. Additionally, THF/n-hexane mixtures were utilized to balance solvent effects and solubility of the reactants, thereby minimizing competitive E2 elimination and affording the desired product in >60% assay yields. To complete the synthesis of tricyclo[6.2.0.03,6]deca-1,3(6),7-trien-2-amine, tricyclo[6.2.0.03,6]deca-1,3(6),7-triene was iodinated using N-iodosuccinimide and subsequently subjected to direct C–N coupling conditions.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"29 9","pages":"2251–2258"},"PeriodicalIF":3.5,"publicationDate":"2025-08-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145094474","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

Hectogram-Scale Synthesis of Carbamates Using Electrochemical Hofmann Rearrangement in Flow 流动中电化学霍夫曼重排合成氨基甲酸酯的百克尺度

IF 3.5 3区化学

Organic Process Research & Development Pub Date : 2025-08-12 DOI: 10.1021/acs.oprd.5c00234

Darryl F. Nater, Rong Zhao, Johannes Rocker, Coline Boche, Dabeen Yun, Bernd Werner, Patrick Löb, Athanassios Ziogas and Siegfried R. Waldvogel*,

引用次数: 0

Co-Catalyst Enabled Biotransformation of Polyunsaturated Fatty Acids for Biobased Monomers 助催化剂使多不饱和脂肪酸转化为生物基单体

IF 3.5 3区化学

Organic Process Research & Development Pub Date : 2025-08-08 DOI: 10.1021/acs.oprd.5c00187

Rebecca N. Re, Caitlin Hudecek, Aanchal Jaisingh, Matthew W. Halloran, Aaron Bruckbauer, Kathryn M. J. Wnuk-Fink, Arushi Dev, Nikita Harwich, Maeva Subileau, James J. La Clair and Michael D. Burkart*,

{"title":"Co-Catalyst Enabled Biotransformation of Polyunsaturated Fatty Acids for Biobased Monomers","authors":"Rebecca N. Re, Caitlin Hudecek, Aanchal Jaisingh, Matthew W. Halloran, Aaron Bruckbauer, Kathryn M. J. Wnuk-Fink, Arushi Dev, Nikita Harwich, Maeva Subileau, James J. La Clair and Michael D. Burkart*, ","doi":"10.1021/acs.oprd.5c00187","DOIUrl":"https://doi.org/10.1021/acs.oprd.5c00187","url":null,"abstract":"Enzymatic lipid epoxidation offers a promising approach to obtain renewable intermediates for biomaterials, but regiochemical control of these reactions has remained elusive. Here we report the discovery and application of artificial cocatalysts to direct the regioselectivity of catalytic epoxidation with the lipase CpLIP2. The methyl esters of alkyl dicarboxylic acids show the unique ability to direct regioselective epoxidation of polyunsaturated fatty acids, major components of plant and algae-based oils. We apply this transformation to the conversion of linoleic acid into sebacic acid, a dicarboxylic acid precursor valuable for biobased polyester polyurethanes, through a six-step pathway involving a regioselective Meinwald rearrangement. To highlight the route’s significance, sebacic acid was used to prepare a 100% biobased thermoplastic polyurethane, illustrating the relevance of this pathway to industrial applications. This regioselective chemoenzymatic oxidation and rearrangement process can be used to access multiple dicarboxylic acids that have remained previously unexplored as biobased monomers.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"29 9","pages":"2265–2274"},"PeriodicalIF":3.5,"publicationDate":"2025-08-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145094414","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

Design Space Visualization and Technoeconomic Evaluation of a Batch Manufacturing Process for the Green Production of an Anti-cancer Drug (Adavosertib) Precursor 抗癌药物Adavosertib前体绿色批量生产工艺的设计空间可视化和技术经济评价

IF 3.5 3区化学

Organic Process Research & Development Pub Date : 2025-08-07 DOI: 10.1021/acs.oprd.5c00056

Matthew Blair, Mazaher Molaei Chalchooghi, Robert J. Cox and Dimitrios I. Gerogiorgis*,

{"title":"Design Space Visualization and Technoeconomic Evaluation of a Batch Manufacturing Process for the Green Production of an Anti-cancer Drug (Adavosertib) Precursor","authors":"Matthew Blair, Mazaher Molaei Chalchooghi, Robert J. Cox and Dimitrios I. Gerogiorgis*, ","doi":"10.1021/acs.oprd.5c00056","DOIUrl":"https://doi.org/10.1021/acs.oprd.5c00056","url":null,"abstract":"The development of cost-effective and sustainable manufacturing processes is a growing priority in the pharmaceutical industry, with many companies turning to computational modeling to reduce reliance on experimental campaigns. Established simulation frameworks must however support in silico pharma R&D, especially for detailed process design and optimization. This paper introduces a robust but simple and flebible modeling framework for simulating and optimizing batch manufacturing processes, applying it to the production of AZD1775 HMS (a small-molecule intermediate required for the synthesis of the experimental anti-cancer drug Adavosertib). The entire design space is mapped using high-fidelity submodels for batch reactors and liquid–liquid extraction (LLE) units. The impact of solvent selection, reagent concentration, separation solvent ratio, operating temperature, and equipment size on process viability has also been evaluated, towards identification of a cost-optimal and environmentally friendly LLE solvent system (water–acetonitrile–toluene) and process conditions. Drug development can thus be streamlined by this systematic pathway for sustainable manufacturing, achieving economic and environmental goals simultaneously.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"29 9","pages":"2178–2199"},"PeriodicalIF":3.5,"publicationDate":"2025-08-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145094454","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

Development of a Multigram Preparation of Optically Pure (−)-7-(Bromomethylene)-3-amidobicyclo[2.2.1]heptane-2-carboxamide BMT-395137, a Versatile Scaffold for Divergent Drug Discovery Synthesis 光学纯(−)-7-（溴乙烯）-3-氨基双环[2.2.1]庚烷-2-羧酰胺BMT-395137的复合图制备，用于发散性药物发现合成的多功能支架

IF 3.5 3区化学

Organic Process Research & Development Pub Date : 2025-08-07 DOI: 10.1021/acs.oprd.5c00208

Jianqing Li*, Daniel Smith, Lyndon Cornelius, Subramaniam Krishnananthan, Peng Li, Dauh-Rurng Wu, Chetan Padmakar Darne, Ning Li, James Kempson, Shun Su, Roshan Y. Nimje, Yoganand Shanmugam, Dyamanna Doddalingappa, Rajesh Krishnan, Anuradha Gupta and Arvind Mathur,

{"title":"Development of a Multigram Preparation of Optically Pure (−)-7-(Bromomethylene)-3-amidobicyclo[2.2.1]heptane-2-carboxamide BMT-395137, a Versatile Scaffold for Divergent Drug Discovery Synthesis","authors":"Jianqing Li*, Daniel Smith, Lyndon Cornelius, Subramaniam Krishnananthan, Peng Li, Dauh-Rurng Wu, Chetan Padmakar Darne, Ning Li, James Kempson, Shun Su, Roshan Y. Nimje, Yoganand Shanmugam, Dyamanna Doddalingappa, Rajesh Krishnan, Anuradha Gupta and Arvind Mathur, ","doi":"10.1021/acs.oprd.5c00208","DOIUrl":"https://doi.org/10.1021/acs.oprd.5c00208","url":null,"abstract":"This paper describes the development of a synthetic route for the multigram synthesis of (−)-(1R,2S,3R,4R,Z)-7-(bromomethylene)-N-(4-fluoro-3-(trifluoromethyl)phenyl)-3-(2,2,2-trifluoroacetamido)bicyclo[2.2.1]heptane-2-carboxamide ((−)-14, BMT-395173), a versatile scaffold for divergent drug discovery synthesis. This new process begins with readily available commercial starting materials and includes a highly scalable stereoselective Diels–Alder reaction between (Z)-4-(benzyloxy)-4-oxobut-2-enoic acid (21) and ferrocenium hexafluorophosphate (15), resulting in the formation of alcohol rac-20. Additionally, a stereoselective Wittig reaction of ketone rac-10 with (bromomethyl)triphenylphosphonium bromide introduces the bromomethylene group of (−)-14. The process was applied to the preparation of over 100 g of optically pure BMS-395173 via multiple batches for preclinical chemotype optimization.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"29 8","pages":"2107–2115"},"PeriodicalIF":3.5,"publicationDate":"2025-08-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144840634","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

Recent Advances in Nonprecious Metal Catalysis 非贵金属催化研究进展

IF 3.5 3区化学

Organic Process Research & Development Pub Date : 2025-08-06 DOI: 10.1021/acs.oprd.5c00191

David C. Cabanero, Avelyn Mae Delos Reyes, Xuan Ju, Xu Ma, Jenna L. Payne* and Suttipol Radomkit*,

引用次数: 0

Development of a Manufacturing Process for a Key (S)-5-(2,2-Dimethyltetrahydro-2H-pyran-4-yl)-1H-indole Intermediate for Orforglipron. Part I. Selection of an Evans Auxiliary-Assisted Asymmetric 1,4-Addition Route 甲氟格列酮中间体(S)-5-（2,2-二甲基四氢- 2h -吡喃-4-基）- 1h -吲哚的制备工艺研究第一部分：一种Evans辅助-辅助非对称1,4-加成路径的选择

IF 3.5 3区化学

Organic Process Research & Development Pub Date : 2025-08-05 DOI: 10.1021/acs.oprd.5c00183

Qiang Yang*, Alison Campbell Brewer, Sarah J. Ryan, Derek R. Starkey, Radhe K. Vaid, Ping Huang, Mo Jia, Peng Liu, Lixuan Liang, Lingxing Meng, Manabu Wadamoto, Satoshi Tsuchiya, Fumiki Kawagishi, Akemi Mizutani and Minoru Yamawaki,

{"title":"Development of a Manufacturing Process for a Key (S)-5-(2,2-Dimethyltetrahydro-2H-pyran-4-yl)-1H-indole Intermediate for Orforglipron. Part I. Selection of an Evans Auxiliary-Assisted Asymmetric 1,4-Addition Route","authors":"Qiang Yang*, Alison Campbell Brewer, Sarah J. Ryan, Derek R. Starkey, Radhe K. Vaid, Ping Huang, Mo Jia, Peng Liu, Lixuan Liang, Lingxing Meng, Manabu Wadamoto, Satoshi Tsuchiya, Fumiki Kawagishi, Akemi Mizutani and Minoru Yamawaki, ","doi":"10.1021/acs.oprd.5c00183","DOIUrl":"https://doi.org/10.1021/acs.oprd.5c00183","url":null,"abstract":"Two synthetic strategies for key (S)-5-(2,2-dimethyltetrahydro-2H-pyran-4-yl)-1H-indole intermediate 1 for orforglipron were demonstrated. The Negishi cross-coupling route was initially scaled up to deliver a total of 36.6 kg of compound 1 to support the production of orforglipron to fund early clinical trials. However, this route was nonenantioselective and required laborious chiral SFC purification to obtain an optically pure intermediate. An enantioselective route featuring Evans auxiliary-assisted asymmetric 1,4-addition successfully produced the desired product without necessitating nonscalable chromatographic purification throughout the synthesis, which was selected for further development into a robust process for large-scale production.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"29 8","pages":"1994–2004"},"PeriodicalIF":3.5,"publicationDate":"2025-08-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144840671","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

Development of a Manufacturing Process for a Key (S)-5-(2,2-Dimethyltetrahydro-2H-pyran-4-yl)-1H-indole Intermediate for Orforglipron. Part III. Development of a Telescoped Phase-Transfer-Catalyzed Alkylation and Cyclopropanation Process 甲氟格列酮中间体(S)-5-（2,2-二甲基四氢- 2h -吡喃-4-基）- 1h -吲哚的制备工艺研究第三部分。缩合相转移催化烷基化和环丙烷化工艺的发展

IF 3.5 3区化学

Organic Process Research & Development Pub Date : 2025-08-05 DOI: 10.1021/acs.oprd.5c00185

Qiang Yang*, Derek R. Starkey, Jingfan Yang, Radhe K. Vaid, Peng-Kai Kao, Charles B. Held, Mark D. Argentine, Derek Berglund, Alison Campbell Brewer, Jonas Y. Buser, Kayla L. Mathews, Ping Huang, Mo Jia, Peng Liu, Jing Chen and Fangyun Yang,

{"title":"Development of a Manufacturing Process for a Key (S)-5-(2,2-Dimethyltetrahydro-2H-pyran-4-yl)-1H-indole Intermediate for Orforglipron. Part III. Development of a Telescoped Phase-Transfer-Catalyzed Alkylation and Cyclopropanation Process","authors":"Qiang Yang*, Derek R. Starkey, Jingfan Yang, Radhe K. Vaid, Peng-Kai Kao, Charles B. Held, Mark D. Argentine, Derek Berglund, Alison Campbell Brewer, Jonas Y. Buser, Kayla L. Mathews, Ping Huang, Mo Jia, Peng Liu, Jing Chen and Fangyun Yang, ","doi":"10.1021/acs.oprd.5c00185","DOIUrl":"https://doi.org/10.1021/acs.oprd.5c00185","url":null,"abstract":"A scalable 8-step route for a key (S)-5-(2,2-dimethyltetrahydro-2H-pyran-4-yl)-1H-indole intermediate for orforglipron was developed to support clinical trials. Highlights of process development results in this contribution include the following: (1) approximately 50% reduction of a key des-carbonyl impurity in the reductive removal of the Evans auxiliary by the introduction of MgCl2 as a chelating agent for the reduction with LiBH4, (2) a telescoped process for PTC alkylation with chloroacetonitrile and subsequent cyclopropyl ring formation with an asymmetric cyclic sulfate avoiding the problematic isolation of the alkylation product, and (3) significantly improved isolated yield and stereoselectivity of the cyclopropyl ring formation by replacing KHMDS with LiOt-Bu as the base for the reaction. The developed process was successfully scaled up to >400 kg scale for each step to deliver a high-quality product in an overall yield of 22%, demonstrating the robustness of the optimized process.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"29 8","pages":"2018–2029"},"PeriodicalIF":3.5,"publicationDate":"2025-08-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144840480","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