Organic Process Research & Development最新文献

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Analytical Control Strategies for Process Chemists
IF 3.1 3区 化学
Organic Process Research & Development Pub Date : 2025-02-21 DOI: 10.1021/acs.oprd.5c0004010.1021/acs.oprd.5c00040
Saranjit Singh*, 
{"title":"Analytical Control Strategies for Process Chemists","authors":"Saranjit Singh*, ","doi":"10.1021/acs.oprd.5c0004010.1021/acs.oprd.5c00040","DOIUrl":"https://doi.org/10.1021/acs.oprd.5c00040https://doi.org/10.1021/acs.oprd.5c00040","url":null,"abstract":"","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"29 2","pages":"209–211 209–211"},"PeriodicalIF":3.1,"publicationDate":"2025-02-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143452515","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
Analytical Control Strategies for Process Chemists
IF 3.4 3区 化学
Organic Process Research & Development Pub Date : 2025-02-21 DOI: 10.1021/acs.oprd.5c00040
Saranjit Singh
{"title":"Analytical Control Strategies for Process Chemists","authors":"Saranjit Singh","doi":"10.1021/acs.oprd.5c00040","DOIUrl":"https://doi.org/10.1021/acs.oprd.5c00040","url":null,"abstract":"Published as part of <i>Organic Process Research & Development</i> special issue “Analytical Control Strategies for Process Chemists”. Increased resource utilization, which can be achieved through atom economy leading to higher selectivity and high yields, minimization of byproducts formation (impurity rejection), and hence waste reduction. Simplicity and safety of processes, which means the involvement of minimal steps and use of readily available, safe, and environmentally friendly reagents and solvents. Also, the use of mild temperatures, pressures, and reagents leads to minimized energy consumption, reduced risk of hazardous conditions, and hence low environmental impact and better sustainability. Scalability and robustness, where the requirement is that the process should be readily scalable from laboratory to industrial production without significant changes in yield or selectivity and insensitive to minor variations in operating conditions or raw materials, ensuring consistent product quality. Cost-effectiveness, which refers to minimizing the overall cost of the process, including raw materials, energy, and waste disposal, to ensure economic viability. Regulatory compliance, in line with increasingly stringent policies from worldwide regulatory bodies toward assurance of product quality and patient safety in the case of pharmaceuticals and biopharmaceuticals. Use of strategies like constant monitoring and precise control of reaction conditions, such as temperature, pressure, pH, cooling rate, rotation speed, etc. The reactions with multiple steps and competing pathways can be challenging to control. In these situations, strategies like selective catalysis, precise dosing of reagents, and real-time monitoring of key intermediates can be used to steer the reaction toward the desired product. Analytical control strategies are essential for ensuring the quality of the product and consistency of organic processes. These strategies involve the use of various analytical techniques to monitor and optimize reaction conditions, track the formation of products and byproducts, and ensure that the final product meets the required specifications. Variations in raw materials, equipment performance, or operating conditions can lead to inconsistencies in product quality between different batches. To address this, strategies like statistical process control, detailed documentation of process parameters, and robust process design are employed. For example, in the production of an active drug substance, monitoring critical process parameters can help ensure consistent product quality across different batches. By providing real-time information about the composition of the reaction mixtures, analytical techniques enable scientists to gain a deeper understanding of reaction mechanisms and kinetics for controlling the product quality and cycle time. This knowledge is crucial for developing efficient and robust processes. Analytical techniques help identify ","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"13 1","pages":""},"PeriodicalIF":3.4,"publicationDate":"2025-02-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143463019","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 Commercial Ready Process for TNG908: A Potent, Selective, and Brain-Penetrant MTA-Cooperative PRMT5 Inhibitor
IF 3.4 3区 化学
Organic Process Research & Development Pub Date : 2025-02-20 DOI: 10.1021/acs.oprd.5c00017
Jianglin Colin Liang, Hongming Li, Kevin M. Cottrell, Yong Liu, John P. Maxwell, Zhengyang Xin, Luigi Anzalone, Magnus Ronn, Michael A. Palmieri, Jr.
{"title":"Development of a Commercial Ready Process for TNG908: A Potent, Selective, and Brain-Penetrant MTA-Cooperative PRMT5 Inhibitor","authors":"Jianglin Colin Liang, Hongming Li, Kevin M. Cottrell, Yong Liu, John P. Maxwell, Zhengyang Xin, Luigi Anzalone, Magnus Ronn, Michael A. Palmieri, Jr.","doi":"10.1021/acs.oprd.5c00017","DOIUrl":"https://doi.org/10.1021/acs.oprd.5c00017","url":null,"abstract":"<b>TNG908</b> is a potent, selective, and brain-penetrant MTA-cooperative PRMT5 inhibitor for the treatment of <i>MTAP</i>-deleted tumors. We describe here the chemical process development for the synthesis of <b>TNG908</b> and the improvements that were achieved over the medicinal chemistry route with much higher yields and better purities. This commercial ready process is convergent, diastereoselective, safe, reproducible, and robust. A total of eight GMP batches have been successfully manufactured, resulting in high-purity API meeting all specifications.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"230 1","pages":""},"PeriodicalIF":3.4,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143463018","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 Commercial Ready Process for TNG908: A Potent, Selective, and Brain-Penetrant MTA-Cooperative PRMT5 Inhibitor
IF 3.1 3区 化学
Organic Process Research & Development Pub Date : 2025-02-20 DOI: 10.1021/acs.oprd.5c0001710.1021/acs.oprd.5c00017
Jianglin Colin Liang*, Hongming Li, Kevin M. Cottrell, Yong Liu, John P. Maxwell, Zhengyang Xin, Luigi Anzalone, Magnus Ronn and Michael A. Palmieri Jr., 
{"title":"Development of a Commercial Ready Process for TNG908: A Potent, Selective, and Brain-Penetrant MTA-Cooperative PRMT5 Inhibitor","authors":"Jianglin Colin Liang*,&nbsp;Hongming Li,&nbsp;Kevin M. Cottrell,&nbsp;Yong Liu,&nbsp;John P. Maxwell,&nbsp;Zhengyang Xin,&nbsp;Luigi Anzalone,&nbsp;Magnus Ronn and Michael A. Palmieri Jr.,&nbsp;","doi":"10.1021/acs.oprd.5c0001710.1021/acs.oprd.5c00017","DOIUrl":"https://doi.org/10.1021/acs.oprd.5c00017https://doi.org/10.1021/acs.oprd.5c00017","url":null,"abstract":"<p ><b>TNG908</b> is a potent, selective, and brain-penetrant MTA-cooperative PRMT5 inhibitor for the treatment of <i>MTAP</i>-deleted tumors. We describe here the chemical process development for the synthesis of <b>TNG908</b> and the improvements that were achieved over the medicinal chemistry route with much higher yields and better purities. This commercial ready process is convergent, diastereoselective, safe, reproducible, and robust. A total of eight GMP batches have been successfully manufactured, resulting in high-purity API meeting all specifications.</p>","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"29 3","pages":"946–952 946–952"},"PeriodicalIF":3.1,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acs.oprd.5c00017","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143667017","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
A Scalable Process for Synthesizing a Reactive Silicone-Acrylate Monomer
IF 3.1 3区 化学
Organic Process Research & Development Pub Date : 2025-02-19 DOI: 10.1021/acs.oprd.4c0049510.1021/acs.oprd.4c00495
Souvagya Biswas*, Jason S. Fisk*, Michael Telgenhoff, Karin Spiers, Muhunthan Sathiosatham, Thu Vi, Matthew S. Jeletic, Jessica E. Nichols and Travis W. Scholtz, 
{"title":"A Scalable Process for Synthesizing a Reactive Silicone-Acrylate Monomer","authors":"Souvagya Biswas*,&nbsp;Jason S. Fisk*,&nbsp;Michael Telgenhoff,&nbsp;Karin Spiers,&nbsp;Muhunthan Sathiosatham,&nbsp;Thu Vi,&nbsp;Matthew S. Jeletic,&nbsp;Jessica E. Nichols and Travis W. Scholtz,&nbsp;","doi":"10.1021/acs.oprd.4c0049510.1021/acs.oprd.4c00495","DOIUrl":"https://doi.org/10.1021/acs.oprd.4c00495https://doi.org/10.1021/acs.oprd.4c00495","url":null,"abstract":"<p >This study details the route selection, process development, and scale-up of a reactive silicone acrylate monomer, 3-(1,1,1,3,5,5,5-heptamethyltrisiloxane-3-yl)propyl methacrylate. A direct hydrosilylation reaction between allyl (meth)acrylate and 1,1,1,3,5,5,5-heptamethyltrisiloxane in the presence of Karstedt’s catalyst yielded the desired monomer in 46% yield. Two other byproducts were identified: an oxy-silyl ester and a propene hydrosilylated product. Prior to scale-up, the heat release associated with the hydrosilylation reaction was measured using a combination of isothermal reaction microcalorimetry and postreaction differential scanning calorimetry (DSC). The total heat release of hydrosilylation in the observed microcalorimetry experiment was −415 J/g. DSC studies detected the decomposition of the monomer at 280 °C, thereby revealing the risk of decomposition at elevated temperatures. Finding an inhibitor to prevent unwanted free radical polymerization of the monomer during scale-up and product isolation was crucial. 4-Hydroxy TEMPO was identified as the inhibitor of choice during the scale-up and distillation steps to isolate the monomer. Overall, the process optimization described here enabled a reliable, robust, and scalable method to produce multikilogram quantities of the 3-(1,1,1,3,5,5,5-heptamethyltrisiloxan-3-yl)propyl methacrylate monomer. This approach is also expected to be suitable for other reactive silicone-acrylate-based monomers.</p>","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"29 3","pages":"760–768 760–768"},"PeriodicalIF":3.1,"publicationDate":"2025-02-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143666947","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
Practical Synthesis of Oxepanoprolines
IF 3.1 3区 化学
Organic Process Research & Development Pub Date : 2025-02-19 DOI: 10.1021/acs.oprd.4c0052110.1021/acs.oprd.4c00521
Kelvin J. Y. Wu, Priscilla Liow and Andrew G. Myers*, 
{"title":"Practical Synthesis of Oxepanoprolines","authors":"Kelvin J. Y. Wu,&nbsp;Priscilla Liow and Andrew G. Myers*,&nbsp;","doi":"10.1021/acs.oprd.4c0052110.1021/acs.oprd.4c00521","DOIUrl":"https://doi.org/10.1021/acs.oprd.4c00521https://doi.org/10.1021/acs.oprd.4c00521","url":null,"abstract":"<p >A new, more scalable route for the synthesis of the common oxepanoproline southern fragment of the antibiotic candidates iboxamycin, cresomycin, and BT-33 is presented. A key transformation in the route is a diastereoselective TiCl<sub>4</sub>-mediated conjugate addition of an allylsilane to an Evans <i>N</i>-acryloyloxazolidinone, followed by <i>syn</i>-aldol addition of the resultant titanium enolate to (<i>R</i>)-Garner’s aldehyde, which assembles all the stereocenters within the target molecule in a single operation.</p>","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"29 3","pages":"828–835 828–835"},"PeriodicalIF":3.1,"publicationDate":"2025-02-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143666948","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
Solvent-Free Production of Triacetin from Glycerol through Complementary Mechanochemical, Biphasic, and Catalytic Approaches Using ICHeM Technology
IF 3.4 3区 化学
Organic Process Research & Development Pub Date : 2025-02-19 DOI: 10.1021/acs.oprd.4c00501
Remi Nguyen, Samy Halloumi, Irene Malpartida, Christophe Len
{"title":"Solvent-Free Production of Triacetin from Glycerol through Complementary Mechanochemical, Biphasic, and Catalytic Approaches Using ICHeM Technology","authors":"Remi Nguyen, Samy Halloumi, Irene Malpartida, Christophe Len","doi":"10.1021/acs.oprd.4c00501","DOIUrl":"https://doi.org/10.1021/acs.oprd.4c00501","url":null,"abstract":"Impact in Continuous Flow Heated Mechanochemistry (ICHeM) was utilized for the biphasic acetylation of glycerol with immiscible acetic anhydride in the presence of homogeneous acid catalysts. This innovative technology combines efficient phase dispersion with continuous flow, offering the following benefits: (i) improved mixing of the two immiscible components (liquid glycerol and highly reactive acetic anhydride); (ii) mechanochemical energy generated by bead impact in continuous flow, eliminating the need for additional heating energy; and (iii) an alternative to single- and double-screw extruders, which are ineffective with liquid reaction media. Under our optimized conditions, triacetin “<i>t</i>” can be obtained with a 99% yield (100% conversion and 99% selectivity) in a solvent-free biphasic continuous flow process with a residence time of 15–30 min, using efficient homogeneous Lewis acids like iron triflate II or Brönsted acids like sulfuric acid.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"19 1","pages":""},"PeriodicalIF":3.4,"publicationDate":"2025-02-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143462974","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
Thermal Hazard Assessment of the Synthesis of 1,1′-Azobis-1,2,3-triazole
IF 3.4 3区 化学
Organic Process Research & Development Pub Date : 2025-02-19 DOI: 10.1021/acs.oprd.4c00404
Hao Li, Jin-Xi Wu, Guang-Yuan Zhang, Ning-Ning Du, Le-Wu Zhan, Jing Hou, Bin-Dong Li
{"title":"Thermal Hazard Assessment of the Synthesis of 1,1′-Azobis-1,2,3-triazole","authors":"Hao Li, Jin-Xi Wu, Guang-Yuan Zhang, Ning-Ning Du, Le-Wu Zhan, Jing Hou, Bin-Dong Li","doi":"10.1021/acs.oprd.4c00404","DOIUrl":"https://doi.org/10.1021/acs.oprd.4c00404","url":null,"abstract":"Azo energetic compounds have attracted much attention due to their high heat of formation and high oxygen balance. However, due to a lack of safety research on this manufacturing process, industrial production cannot be carried out. 1,1′-Azobis-1,2,3-triazole was chosen as an example to identify hazardous scenarios in the synthesis of azo-energetic materials. First, the properties of the 1,1′-azobis-1,2,3-triazole synthesis experiment were studied using a reaction calorimeter (RC1). Afterward, the thermal stability of the composite materials used in the synthesis process was evaluated using accelerating rate calorimetry (ARC) and differential scanning calorimetry (DSC). DSC results showed that the heat release of the mixture was significantly reduced in all three steps. ARC experiments showed that the <i>T</i><sub>D24</sub> values of the three substances are in the range of 100.00–300.00 °C. RC1 experiments showed that the adiabatic temperature rises (Δ<i>T</i><sub>ad</sub>) in the whole process are 91.26 54.19, 51.49, and 4.10 K, respectively. These findings indicate that the exothermic reaction involved in the synthesis of 1,1′-azobis-1,2,3-triazole is initiated during the dosing phase and is affected by the dosing rate. The overall 1,1′-azobis-1,2,3-triazole synthesis process is a criticality class 1 of a chemical reaction. This holistic approach furnishes valuable data and insights for improving the engineering safety protocols of 1,1′-azobis-1,2,3-triazole, aimed at mitigating risks in industrial operations.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"15 1","pages":""},"PeriodicalIF":3.4,"publicationDate":"2025-02-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143452313","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
Practical Synthesis of Oxepanoprolines
IF 3.4 3区 化学
Organic Process Research & Development Pub Date : 2025-02-19 DOI: 10.1021/acs.oprd.4c00521
Kelvin J. Y. Wu, Priscilla Liow, Andrew G. Myers
{"title":"Practical Synthesis of Oxepanoprolines","authors":"Kelvin J. Y. Wu, Priscilla Liow, Andrew G. Myers","doi":"10.1021/acs.oprd.4c00521","DOIUrl":"https://doi.org/10.1021/acs.oprd.4c00521","url":null,"abstract":"A new, more scalable route for the synthesis of the common oxepanoproline southern fragment of the antibiotic candidates iboxamycin, cresomycin, and BT-33 is presented. A key transformation in the route is a diastereoselective TiCl<sub>4</sub>-mediated conjugate addition of an allylsilane to an Evans <i>N</i>-acryloyloxazolidinone, followed by <i>syn</i>-aldol addition of the resultant titanium enolate to (<i>R</i>)-Garner’s aldehyde, which assembles all the stereocenters within the target molecule in a single operation.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"32 1","pages":""},"PeriodicalIF":3.4,"publicationDate":"2025-02-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143452314","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
A Scalable Process for Synthesizing a Reactive Silicone-Acrylate Monomer
IF 3.4 3区 化学
Organic Process Research & Development Pub Date : 2025-02-19 DOI: 10.1021/acs.oprd.4c00495
Souvagya Biswas, Jason S. Fisk, Michael Telgenhoff, Karin Spiers, Muhunthan Sathiosatham, Thu Vi, Matthew S. Jeletic, Jessica E. Nichols, Travis W. Scholtz
{"title":"A Scalable Process for Synthesizing a Reactive Silicone-Acrylate Monomer","authors":"Souvagya Biswas, Jason S. Fisk, Michael Telgenhoff, Karin Spiers, Muhunthan Sathiosatham, Thu Vi, Matthew S. Jeletic, Jessica E. Nichols, Travis W. Scholtz","doi":"10.1021/acs.oprd.4c00495","DOIUrl":"https://doi.org/10.1021/acs.oprd.4c00495","url":null,"abstract":"This study details the route selection, process development, and scale-up of a reactive silicone acrylate monomer, 3-(1,1,1,3,5,5,5-heptamethyltrisiloxane-3-yl)propyl methacrylate. A direct hydrosilylation reaction between allyl (meth)acrylate and 1,1,1,3,5,5,5-heptamethyltrisiloxane in the presence of Karstedt’s catalyst yielded the desired monomer in 46% yield. Two other byproducts were identified: an oxy-silyl ester and a propene hydrosilylated product. Prior to scale-up, the heat release associated with the hydrosilylation reaction was measured using a combination of isothermal reaction microcalorimetry and postreaction differential scanning calorimetry (DSC). The total heat release of hydrosilylation in the observed microcalorimetry experiment was −415 J/g. DSC studies detected the decomposition of the monomer at 280 °C, thereby revealing the risk of decomposition at elevated temperatures. Finding an inhibitor to prevent unwanted free radical polymerization of the monomer during scale-up and product isolation was crucial. 4-Hydroxy TEMPO was identified as the inhibitor of choice during the scale-up and distillation steps to isolate the monomer. Overall, the process optimization described here enabled a reliable, robust, and scalable method to produce multikilogram quantities of the 3-(1,1,1,3,5,5,5-heptamethyltrisiloxan-3-yl)propyl methacrylate monomer. This approach is also expected to be suitable for other reactive silicone-acrylate-based monomers.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"15 1","pages":""},"PeriodicalIF":3.4,"publicationDate":"2025-02-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143462973","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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