CHEMPHYSCHEM
·
2017
·Vol. 18
·期 22
·3182-3188
·
IF 3.075
Xue-Dong Li,Qing-Wen Song,Xian-Dong Lang,Yao Chang,Liang-Nian He
Graphical Heterocycle promotion : An Ag 2 O/TMG (1,1,3,3-tetramethylguanidine) promoted substrate-driven and divergent route leads to a variety of heterocycles from propargyl alcohols, CO 2 , and 2-aminoethanols with turnover numbers up to 1260. The reaction proceeds through a cascade pathway with α-alkylidene cyclic carbonate as the intermediate. Chemical valorization of CO 2 to access various value-added compounds has been a long-term and challenging objective from the viewpoint of sustainable chemistry. Herein, a one-pot three-component reaction of terminal propargyl alcohols, CO 2 , and 2-aminoethanols was developed for the synthesis of 2-oxazolidinones and an equal amount of α-hydroxyl ketones promoted by Ag 2 O/TMG (1,1,3,3-tetramethylguanidine) with a TON (turnover number) of up to 1260. By addition of terminal propargyl alcohol, the thermodynamic disadvantage of the conventional 2-aminoethanol/CO 2 coupling was ameliorated. Mechanistic investigations including control experiments, DFT calculation, kinetic and NMR studies suggest that the reaction proceeds through a cascade pathway and TMG could activate propargyl alcohol and 2-aminoethanol through the formation of hydrogen bonds and also activate CO 2 .
研究领域:
有机化学
·
绿色化学
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DOI
PubMed
高影响因子
PROGRESS IN ORGANIC COATINGS
·
2022
·
IF 6.206
Yinlei Lin,Xinyan Song,Chenjing Zhu,Jianhui Huang,Xiaoxu Bai,Haichen Zhang,Kun Wang,Huawen Hu,Guangji Li
The self-healing properties of the material synthesized based on conventional isocyanate microcapsules as a healing agent are most likely degraded by the release of CO 2 during self-healing. Herein, we report the self-healing capability in a moisture environment of a particle-encapsulated isocyanate that is activated through the curing process involving an isocyanate agent. A novel isocyanate–oxazolidine compound loaded-spherical microcapsule, with a shell thickness of 10 μm and a median diameter of 151.4 μm, is first prepared via interfacial photoinitiated thiol-ene click chemistry in a stabilized aqueous emulsion. The encapsulation of the synthesized oxazolidine enables a significant improvement in the thermal stability of the microcapsules. Furthermore, the evaluation and analysis of the self-healing properties of the polyurethane coatings based on the isocyanate–oxazolidine-loaded microcapsules provide the evidence to elucidate the self-healing pathway on the molecular level. The oxazolidine preferentially undergoes a ring-opening reaction, yielding amino and hydroxyl compounds that further react with isocyanate to achieve autonomous self-healing in a moisture environment. This study opens up a route to develop isocyanate-encapsulated self-healing materials for practical applications.
研究领域:
材料科学
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化学工程
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产品关联
DOI
高影响因子
ACS Sustainable Chemistry & Engineering
·
2017
·
IF 5.951
Mei Li,Jianling Xia,Wei Mao,Xuejuan Yang,Lina Xu,Kun Huang,Shouhai Li
Dual cross-linked polymer networks (DCPNs) are novel copolymers containing two different cross-linking polymers with superior comprehensive properties. The aim of this study was to explore the feasibility of preparation of novel castor oil-based DCPNs material. First, two novel biobased reactive monomers of epoxidized castor oil (ECO) and ricinoleic acid epoxy (RAE), containing both hydroxy and epoxy groups, were synthesized from castor oil (CO). Their chemical structures were characterized by Fourier transforminfrared spectroscopy (FTIR) and 1H-nuclear magnetic resonance (1H NMR) analysis. Both hydroxy and epoxy groups can react with the isocyanate groups of toluene-2,4-diisocyanate (TDI), and then two renewable resource-based DCPNs of RAE/TDI and ECO/TDI, containing both polyurethane (PU) and polyoxazolidinone (POXDN) molecular structures, were designed and prepared. The tensile properties, gel content (GC), hardness, fractured surface morphologies, thermostabilities, and dynamic mechanical and thermal properties of these renewable resource-based copolymers were all investigated. Results show that the tensile properties, GC, hardness, and glass transition temperature (Tg) of the fabricated DCPNs were superior to those of the pure CO/TDI copolymerized system. The fabricated DCPNs, particularly RAE/TDI, were found to have good tensile strength of 12.47 MPa and the highest elongation at break of 154.99%, and its thermostability was also increased greatly compared with that of the pure CO/TDI copolymerized system.
研究领域:
材料科学
·
高分子化学
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产品关联
DOI
高影响因子
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH
·
2023
·
IF 4.2
Xiaoyan Zheng,Tianhao Zhang,Jie Li,Guoliang Zhang,Hongnan Chen,Shasha Cao,Chunshan Li,Guangzhou Jin
2-Ethyl-3-oxazolidineethanol (OE) is an important pharmaceutical intermediate for the treatment of dental plaque. A systematic investigation of the one-pot synthesis of OE from propanal (PA) and diethanolamine (DEA) was conducted herein. The process was carried out under mild reaction conditions without any addition of catalyst, and the product was characterized by Fourier transform infrared spectroscopy (FT-IR), 1H nuclear magnetic resonance (NMR), and electrospray ionization-tandem mass spectrometry (ESI-MS/MS). Additionally, the effects of the PA/DEA ratio, methanol/DEA ratio, reaction time, and temperature on the reaction results were explored. Based on the single-factor experiments, response surface methodology (RSM) was used to optimize the reaction conditions and it achieved a high OE yield of 98.48%, which is close to the prediction value of 98.38%. Furthermore, the reaction kinetics were calculated utilizing the second-order kinetic model, and activation energies of the forward and reverse reactions were 31.35 and 41.85 kJ·mol–1, respectively. Under the optimization reaction conditions, OE was efficiently synthesized, indicating a significant potential for industrial applications.
研究领域:
有机化学
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制药工程
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化工过程优化
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产品关联
DOI
高影响因子
MOLECULES
·
2018
·Vol. 23
·期 11
·3033
·
IF 3.098
Shumei Xia,Yu Song,Xuedong Li,Hongru Li,Liang-Nian He
To circumvent the thermodynamic limitation of the synthesis of oxazolidinones starting from 2-aminoethanols and CO2and realize incorporation CO2under atmospheric pressure, a protic ionic liquid-facilitated three-component reaction of propargyl alcohols, CO2and 2-aminoethanols was developed to produce 2-oxazolidinones along with equal amount of α-hydroxyl ketones. The ionic liquid structure, reaction temperature and reaction time were in detail investigated. And 15 mol% 1,5,7-triazabicylo[4.4.0]dec-5-ene ([TBDH][TFE]) trifluoroethanol was found to be able to synergistically activate the substrate and CO2, thus catalyzing this cascade reaction under atmospheric CO2pressure. By employing this task-specific ionic liquid as sustainable catalyst, 2-aminoethanols with different substituents were successfully transformed to 2-oxazolidinones with moderate to excellent yield after 12 h at 80 °C.Keywords:ionic liquid;synergistic activation;aminoethanol;2-oxazolidinone;atmospheric CO2;sustainable catalysis
研究领域:
有机化学
·
绿色化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
PEST MANAGEMENT SCIENCE
·
2020
·Vol. 77
·期 1
·177-183
·
IF 3.75
Yuan-Yuan Zhang,Shuang Gao,Minh-Tu Hoang,Zi-Wei Wang,Xin Ma,Yue Zhai,Na Li,Li-Xia Zhao,Ying Fu,Fei Ye
BACKGROUND Herbicide safeners mitigate crop damage without reducing herbicide efficacy. Here, the protective effects of phenoxyacetyl oxazolidine derivatives as potential safeners were evaluated with a view toward reducing injury caused by sulfonylurea herbicide nicosulfuron to sensitive maize varieties. RESULTS Growth indices demonstrated that the bioactivity of compound 9 ( N -phenoxyacety-2-methyl-2,4-diethyl-1,3-oxazolidine) was superior to that of R-28725 and all other compounds tested. Compound 9 induced endogenous glutathione and upregulated glutathione- S -transferase (GST) in maize. Thus, it could enhance maize tolerance to nicosulfuron. Compared with the untreated water control group, the maximum reaction rate of GST was increased by 37.62%, while the maximum velocity of GST was decreased by 61.93% after treatment with compound 9 . Acetolactate synthase relative activity was significantly enhanced in the case of treatment with compound 9 , indicating the excellent protective effects of compound 9 against nicosulfuron in maize. CONCLUSIONS The present work demonstrates that phenoxyacetyl oxazolidine derivatives are potentially efficacious as herbicide safeners and merit further investigation.
研究领域:
植物保护学
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农药科学
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产品关联
DOI
PubMed
高影响因子
SENSORS AND ACTUATORS B-CHEMICAL
·
2021
·
IF 7.46
Lihong Su,Yaqian Chen,Lulu Wang,Han Zhang,Jing Sun,Jianlong Wang,Daohong Zhang
As a point-of-care testing method, lateral flow immunoassays are attracting extensive attentions for antibiotic residue detections; however, immunoassay techniques for qualitative and quantitative detections are limited by the poor sensitivity and requirement for cumbersome quantitative devices. To overcome these limitations, MnO 2 -Au, with an excellent carrying capacity of Au nanoparticles and high photothermal signals, was introduced and a dual-signal immunoassay using colorimetric/photothermal MnO 2 -Au signal probe was proposed for furazolidone (FZD) detection. The dual-signal immunoassay not only enables visual detection relying on color change, but also enables quantitative detection via converting conventional assay signals into heat signals using a thermal infrared imager recording. Based on the excellent light-to-heat conversion activity of the bifunctional MnO 2 -Au, the FZD metabolite of 3-amino-2-oxazolidinone (AOZ) can be qualitatively detected in virtue of colorimetric signals with a visual limit of 1 ng mL −1 and quantitatively detected by photothermal signals with a detection limit of 0.43 ng mL −1 . The dual-signal immunoassay biosensor was well applied in food samples with acceptable recoveries of 80.6–106 %. The immunoassay that integrates colorimetric and photothermal analysis will hold a broader application area in real-time monitoring.
研究领域:
分析化学
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食品科学
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生物医学工程
✓ 已验证
产品关联
DOI
高影响因子
Polymer Chemistry
·
2016
·Vol. 7
·期 33
·5273-5280
·
IF 5.687
Qingkai Qi,Yue Li,Xiaoyu Yan,Fengli Zhang,Shan Jiang,Jing Su,Bin Xu,Xueqi Fu,Liankun Sun,Wenjing Tian
A novel amphiphilic copolymer consisting of tetraphenylethylene-oxazolidine (TPE-OX) as a pH-sensitive chromophore and poly(ethylene glycol) methyl ether methacrylate (PEGMA) as a water-soluble chain has been well designed and synthesized. A self-assembled polymeric micelle based on the copolymer exhibited clear dual-emission switching between cyan and red with a decrease of pH value in Tris-HCl buffer solution due to the extended conjugation and emerging intramolecular charge transfer effect when opening the spiro-ring of OX moiety. Fluorescence imaging of HepG2 cells stained by the polymeric micelle shows switched luminescence from cyan to red with high selectivity and contrast, indicating that the polymeric micelle was an effective probe for intracellular pH detection. Additionally, the red emission of the polymeric micelle in lysosomes can reversibly switch back to the original cyan emission in response to the two lysosomal activity inhibitors chloroquine and bafilomycin, which demonstrates that the polymeric micelle has potential applications in detecting the activity of lysosomal and further autophagy in cancer cells.
研究领域:
材料科学
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生物材料
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细胞生物学
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癌症研究
✓ 已验证
产品关联
DOI
高影响因子
FOOD CHEMISTRY
·
2021
·
IF 7.514
Jingke Xu,Leina Dou,Sijie Liu,Lihong Su,Xuechi Yin,Jing Ren,Huilan Hu,Daohong Zhang,Jing Sun,Zhanhui Wang,Jianlong Wang
Furazolidone (FZD) and its metabolite called 3-amino-2-oxazolidinone (AOZ) would induce carcinogenic and mutagenic effects to human. In this work, to develop a novel, stable, and simple point of care testing (POCT) with a potential to social applied for FZD detection, we utilized the aspect of protein staining of coomassie brilliant blue (CBB) to exploit a new CBB-LFIA strategy free of NPs. Only one mixing step is needed during the probe manufacturing process, which requires just 2 h and is a great time saving strategy compared with other methods (requiring 4–33 h for probe preparation). Besides, the cost of CBB-LFIA is 300 times lesser than other LFIA with respect to obtaining the label. The developed CBB-LFIA was successfully applied to detect AOZ with a detection limit of 2 ng mL −1 , without any influence from other potential interfering compounds. The proposed CBB-LFIA exhibited prominent practical application, and possesses considerable utilization potential in the related field.
研究领域:
分析化学
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即时检测
·
食品安全
✓ 已验证
产品关联
DOI
PubMed
高影响因子
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH
·
2025
·
IF 3.9
Zhuo Liu,Cheng Li,Rongxin Zhang,Rude Lin,Zhaowen Dong,Bo Peng,Fan Zhang
Poly(bisphenol A carbonate) (PC) is a widely used engineering plastic that is often disposed of by landfilling or incineration, resulting in severe environmental concerns. Alcohol-aminolysis with ethanolamine can convert PC waste back into its monomer bisphenol A (BPA) and the valuable product 2-oxazolidinone. However, the use of hazardous solvents complicates both the recovery of PC and the synthesis and separation of 2-oxazolidinone. Herein, we developed a sustainable alcohol-aminolysis strategy utilizing the eco-friendly solvent ethanol (EtOH), achieving yields of 93% BPA and 88% 2-oxazolidinone from compact discs in 4 h at 80 °C. Multilinear regression revealed that elevated Kamlet–Taft parameters (β, π*) correlate strongly with enhanced PC alcohol-aminolysis efficiency for most solvents. Conversely, in monohydric alcohols, reactivity exhibits minimal dependence on β- and π*-values but is primarily governed by their steric hindrance. Mechanistic investigation reveals that EtOH enhances the nucleophilicity of ethanolamine, enabling nucleophilic attack on the activated carbonyl group of PC while facilitating cyclization of the intermediate. In gram-scale experiments, we recovered 8.64 g of BPA and 2.96 g of 2-oxazolidinone from 10.16 g of PC using simple filtration and evaporation. Economic assessments show that our innovative process presents a sustainable and economically viable method for upcycling waste polymers into valuable products, eliminating the need for hazardous solvents, harsh conditions, and complex purifications, thereby highlighting its potential for industrial applications.
研究领域:
高分子化学
·
绿色化学
·
废弃物管理
·
有机合成
·
化学工程
✓ 已验证
产品关联
DOI
高影响因子
Catalysis Science & Technology
·
2024
·
IF 4.4
Jinsong Song,Chuanhua Zhou,Xi Chen,Yang Gu,Feng Xue,Qiaqing Wu,Dunming Zhu
Cyanate-mediated epoxide ring-opening by halohydrin dehalogenases (HHDHs) is a promising method for the synthesis of important optically pure 2-oxazolidinones. However, the regio- and stereoselectivity of the naturally occurring HHDHs are still not satisfactory for styrene oxides (SOs). We used a structure-guided semi-rational design to improve the selectivity of HHDHs from Ilumatobacter coccineus (IcHheG), followed by site-saturation and combinatorial mutagenesis of Y18, L103, I104, and N196. The double mutant I104F/N196W showed dramatically improved selectivity toward SOs with excellent regioselectivity (>99 : 1) and stereoselectivity (E > 200), producing the corresponding useful and valuable (S)-4-aryl-2-oxazolidinone and (S)-SO with 98% ee. Moreover, it accepted a wider range of styrene oxides with moderate to excellent selectivity. Analysis of the substrate binding conformations showed that the regio- and stereoselectivity improvement in IcHheG was attributed to an increase of geometric distances to the two carbons and the oxygen atom of the epoxide ring for a single stereoisomer. This study elucidated key structural motifs responsible for regulating the regio- and stereoselectivity of IcHheG, offering theoretical guidance for protein engineering of HHDHs from other organisms.
研究领域:
生物化学
·
生物技术
·
酶工程
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有机化学
·
蛋白质工程
✓ 已验证
DOI
高影响因子
ChemistrySelect
·
2025
·Vol. 10
·期 29
·e00501
·
IF 2
Junjie Zhou,Chaoen Jin,Fan Wang,Yaping Zhu,Huimin Qi
Graphical Under aromatic amine catalysis, the cyanate ester/epoxy system reached 80.6% curing after 5 days at room temperature. Research indicates that adding 20% epoxy resin to pure cyanate ester increases the oxazolidinone content in the cured product, thereby enhancing its flexural strength to 71.43 MPa. This system can be effectively applied to the formulation design of room-temperature fast-curing adhesives. The room-temperature curing behavior of cyanate ester/epoxy resins in the presence of aromatic amines was comprehensively investigated by DSC and FTIR. Additionally, the curing mechanism was confirmed via PY-GC-MS. The results showed that in the reaction system, the catalyst not only promoted the formation of the triazine ring from the cyanate ester but also induced ring opening of the epoxy group. The ring-opened epoxy group then reacted with either the cyanate ester group or the intermediates containing ─C─O═NH to generate oxazolidine. Subsequently, the oxazolidine underwent a rearrangement reaction, leading to the formation of oxazolidinone. After a 5-day reaction at room temperature, the curing degree of the resin system reached 80.6%, thus accomplishing room temperature polymerization. For room-temperature fast-curing adhesive applications, this reaction system not only ensures a relatively short initial curing time but also guarantees a minimum sizing time of 60 min. When the epoxy resin content was 20%, the cured system exhibited a T d5 (5% weight loss temperature) of 323 °C, a flexural strength of 71.43 MPa, and a tensile shear strength of 8.06 MPa, with vacuum volatility meets aerospace standards.
研究领域:
高分子化学
·
材料科学
·
有机化学
·
化学工程
·
胶粘剂技术
✓ 已验证
产品关联
DOI
高影响因子
危险品化学品经营许可证（带存储）