ChemCatChem
·
2022
·Vol. 14
·期 13
·e202200311
·
IF 5.497
Yuyao Zeng,Bowei Wang,Fanyong Yan,Wensheng Xu,Guoyi Bai,Yang Li,Xilong Yan,Ligong Chen
Graphical Through a convenient impregnation method, highly-distributed and stable Cu nanoparticles were dispersed on the boron doped γ-Al 2 O 3 support, which catalyzed continuous reductive amination of levulinic acid to corresponding N-substituted pyrrolidinones. The reductive amination of biomass-derived levulinic acid (LA) to value-added N-substituted pyrrolidinones with amine and molecular hydrogen over heterogeneous catalyst represents an atom-economical and scalable route. In this paper, a series of boron doped Cu/Al 2 O 3 catalysts via kneading and impregnation method are developed for the continuous reductive amination of LA. Compared with Cu/Al 2 O 3 , Cu 10 /AlB 3 O catalyst exhibits greatly improved catalytic performance for this reaction at low operation temperature. Structure-property correlation investigations were performed with diverse characterization methods, and the results revealed that the excellent catalytic performance of boron doped Cu/Al 2 O 3 catalysts was mainly attributed to the synergistic effect of its well-dispersed Cu nanoparticles, appropriate surface Cu electronic state and surface acidic sites nearby. Besides, Cu 10 /AlB 3 O shows great stability during the reaction over 200 h. This work provides a low-cost, efficient and environmentally friendly heterogeneous catalytic system for the continuous production of N-substituted pyrrolidinones.
研究领域:
催化化学
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绿色化学
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生物质转化
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DOI
高影响因子
EUROPEAN POLYMER JOURNAL
·
2025
·
IF 6.3
Qing Gao,Hailin Fu,Hui Liu,Pengfei Li,Jin Shi,Yao Lin,Ziyuan Song
Poly(sarcosine) (PSar)-based diblock copolypeptoid nanoparticles are promising alternatives to PEGylated polymeric nanocarriers. However, their preparation was limited by the slow polymerization kinetics and low assembly concentrations. Herein, we report the facile preparation of copolypeptoid nanoparticles through polymerization-induced self-assembly of N -substituted glycine N -carboxyanhydrides (NNCAs) in solvents with low polarity and weak hydrogen-bonding ability like dichloromethane (DCM). In contrast to the conventional polymerization in N , N -dimethylformamide (DMF), NNCAs were polymerized at an accelerated rate in DCM that minimized side reactions from water and other impurities. With isopentylamine-initiated PSar as the first stabilizing block, the polymerization of N -benzyl glycine N -carboxyanhydrides resulted in the formation of spherical or rod-like nano-assemblies at high solid contents (up to 15%) within several hours. We believe this work not only improves our basic understanding on NNCA polymerization behaviours, but also offers an efficient strategy to prepare drug nanocarriers with PSar corona, facilitating the downstream application studies.
研究领域:
材料科学
·
生物医学工程
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DOI
高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
·
2024
·
IF 5.7
Hui Xu,Jia Ye,Longyuan Lin,Minmin Lian,Jicheng Chen
A novel technique for generating tetramethylpyrazine (TTMP) was proposed, carried out on a phenolics-Fenton coupled redox cycling system in an acetoin-ammonium acetate (AA-ACT) pattern reaction. The TTMP generation employing the Fenton system is a first-order reaction that significantly increased the reaction rate, especially in the early stages, distinguishing it from the original zero-order kinetics reaction pattern. Further, the Fenton reaction effectively promotes the TTMP generation at lower temperature, and epigallocatechin gallate (EGCG) could reset the Fenton reaction, accomplishing the redox cycle. We have discovered a novel class of intermediate products, N-substituted amides, which act as a “reservoir” and transform into amino acid, then undergo aromatization to generate TTMP. The results provide a useful supplement for intelligent synthesis route design, and a new approach for understanding the transformation pathways of pyrazines.
研究领域:
生物化学
·
合成生物学
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DOI
PubMed
高影响因子
NEW JOURNAL OF CHEMISTRY
·
2017
·Vol. 41
·期 19
·10613-10618
·
IF 3.269
Zheng Gong,Yu Lei,Peng Zhou,Zehui Zhang
In this study, the one-pot heterocyclization of nitro compounds with 2,5-hexadione was studied for the synthesis of N-substituted pyrroles via a Paal–Knorr condensation process. The heterogeneous cobalt–nitrogen catalyst (Co–Nx/C-800-AT) was found to be active for this reaction with formic acid. Formic acid served as a hydrogen donor for the transfer hydrogenation, and also acted as an acid catalyst. More importantly, this method was tolerant of other functional groups, and hence various N-substituted pyrroles were produced with good to excellent yields. The Co–Nx/C-800-AT catalyst was highly stable, and could be reused several times without loss of its catalytic activity.
研究领域:
有机化学
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催化化学
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DOI
高影响因子
POLYMER INTERNATIONAL
·
2014
·Vol. 64
·期 4
·563-570
·
IF 2.247
Yi-Ling Huang,Jing Cao,Wei Hu,Sai Liang
Novel optically
active anionic initiators bearing a chiral oxazole substituent on the fluorene ring, ( S )-1-(9H-fluoren-2-yl)-4-isopropyl-4,5-dihydrooxazole lithium (Li-( S )-1-FIDH) and ( S )-2-(9H-fluoren-2-yl)-4-isopropyl-4,5-dihydrooxazole lithium (Li-( S )-2-FIDH), were prepared. Anionic homopolymerizations of achiral N -substituted maleimide (RMI) with the chiral initiators were investigated. The optically active polymers obtained were attributed to asymmetric induction of the chiral initiators. The very crowded chiral initiator Li-( S )-1-FIDH was found to play a better asymmetric induction role in the polymers than Li-( S )-2-FIDH. Anionic copolymerization of ( R )-(+)- N -1-phenylethyl maleimide and optically inactive RMI with Li-( S )-1-FIDH were also studied. © 2014 Society of Chemical Industry
研究领域:
高分子化学
·
有机化学
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DOI
高影响因子
CHINESE JOURNAL OF CHEMISTRY
·
2011
·Vol. 29
·期 9
·1906-1910
·
IF 0.773
Lin Yan,Wenguo Yang,Lixin Li,Yang Shen,Zhiyong Jiang
A mild and facile Wittig reaction between N -substituted maleimides and aldehydes has been developed. Various synthetically valuable alkylidenesuccinimides were obtained from this one-pot reaction in high yields (up to 99%). The product was obtained by simple filtration and no extra purification was necessary. Ethanol, an environment-benign solvent, was found to be a suitable reaction medium.
研究领域:
有机化学
·
药物化学
·
绿色化学
·
合成方法学
·
medicinal chemistry
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DOI
高影响因子
ARCHIV DER PHARMAZIE
·
2019
·Vol. 353
·期 2
·1900231
·
IF 2.145
Xiujie Liu,Xin Chen,Kai Qiu,Zhihao Zhang
A series of 4-methoxy-3-arylamido- N -(substitutedphenyl)benzamides 6a – u were designed according to the splicing principle of structural design in the medicinal chemistry theory and were synthesized in five steps: nitration, acylation, ammoniation, reduction, and secondary ammoniation. The structures of the target compounds were characterized and verified by infrared, 1 H nuclear magnetic resonance (NMR), 13 C NMR, and electron spray ionization spectroscopy. Their in vitro antiplatelet aggregation activities induced by adenosine diphosphate (ADP) or arachidonic acid (AA) were assessed by Born's method. The biological evaluation revealed that all compounds exhibited certain levels of activities in both of the antiplatelet aggregation assays; compounds 6c (IC 50 = 3.84 μM) and 6f (IC 50 = 3.12 μM) displayed the strongest antiplatelet aggregation activities in the ADP-induced and AA-induced assay, separately. Moreover, compounds that had stronger activities were chosen for cell toxicity testing via the cell counting kit-8 assay. The results indicated that none of the compounds had obvious cell toxicity against L929 cells at the doses of 10 and 20 μM. It is worth pointing out that compound 6c showed the highest antiplatelet activity and the lowest cell toxicity. In general, 4-methoxy-3-arylamido- N -(substitutedphenyl)benzamides have the potential to become a kind of safer and more effective antiplatelet agents.
研究领域:
药物化学
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药理学
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DOI
PubMed
高影响因子
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH
·
2024
·
IF 3.8
Tiping Wei,Liguo Wang,Jiajun Zhang,Yan Cao,Xiang Hui,Jianhui Shi,Shuang Xu,Liyan Zhao,Peng He,Huiquan Li
Bio-based pentamethylene dicarbamate (PDC) belongs to N-substituted carbamates, which are important fine chemicals and organic intermediates. In this work, well-defined CeO2 rods, cubes, and octahedrons were successfully prepared to catalyze the synthesis of PDC by carbonylation of 1,5-pentanediamine (PDA) with methyl carbamate (MC). Among them, CeO2 rods with higher amounts of acid–base sites and abundant oxygen vacancies showed superior intrinsic activity in the PDA carbonylation reaction. In situ FTIR results showed that intermediate polyureas were readily formed in the reaction, and then, CeO2 rods promoted the alcoholysis of polyureas to PDC. In situ DRIFTS results indicated that the surface of CeO2 rods is more favorable for the adsorption and activation of the reactants. CeO2 rods can also be used for the efficient synthesis of a series of N-substituted carbamates. We believe that this work will contribute to the efficient, green, and sustainable production of N-substituted carbamates.
研究领域:
催化
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化学工程
·
绿色化学
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材料科学
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产品关联
DOI
高影响因子
Molecular Catalysis
·
2024
·
IF 3.9
Xiangyu Zheng,Zhe Dou,Wenqiang Xiang,Wen Zhang,Ye Ni,Guochao Xu
N -substituted β-amino esters as an important class of chiral amines, are widely used as building blocks in pharmaceuticals. A novel imine reductase Sv IRED was identified through gene mining from Streptomyces viridochromogenes with high enantioselectivity of > 99 % ee (1 R , 2 S ), 95 % de ( cis:trans ), towards 2-oxocyclohexane-1-carboxylate and cyclopropylamine. Sv IRED exhibited the highest activity at pH 7.0 and 40 °C. A variety of amine donors could be used by Sv IRED and produce chiral N -substituted β-amino esters with different enantioselectivity. Employing methylamine ( i ) and pyrrolidine ( n ) as amine donors, Sv IRED exhibited reversed enantioselectivity of 23 % ee (1 S , 2 R ) and 79 % ee (1 S , 2 R ) respectively. Through alanine scanning, M183 and H244 were identified with remarkable roles in governing enantioselectivity towards i and n . Compared with WT Sv IRED, the enantioselectivity of M183A was inverted to ee value of >99 % (1 R , 2 S ) and de value of >99 % ( cis:trans ) towards i , and the enantioselectivity of H244A was inverted to ee value of 88 % (1 R , 2 S ) and de value of >99 % ( cis:trans ) towards n . Interaction analysis indicated the orientation of ester group was vital for manipulation of enantioselectivity. This study provides novel Imine reductase mutants for enantioselective synthesis of N -substituted β -amino esters with different amine donors.
研究领域:
生物化学
·
生物催化
·
酶工程
·
手性合成
·
药物化学
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DOI
高影响因子
BIOMACROMOLECULES
·
2021
·
IF 6.988
Botuo Zheng,Songyi Xu,Xufeng Ni,Jun Ling
Polymerization of N-substituted glycine N-thiocarboxyanhydrides (NNTAs) is a promising pathway to prepare functional polypeptoids benefiting from their tolerance to nucleophilic impurities. However, controlled NNTA polymerization is hard to achieve in amide polar solvents, including N,N-dimethylacetamide (DMAc), N,N-dimethylformamide (DMF), and N-methyl pyrrolidone (NMP), the only aprotic solvents for many biomacromolecules and polypeptoids. In the present work, we successfully achieve controlled NNTA polymerization in amide polar solvents by adding acetic acid as a promoter. The promotion is applied to the polymerization of sarcosine NTA, N-ethyl glycine NTA, and N-butyl glycine NTA. DMAc, DMF, and NMP are suitable solvents to prepare polypeptoids with designable molecular weights and low dispersities (1.06–1.21). The polysarcosines with high molecular weights are prepared up to 35.2 kg/mol. A kinetic investigation quantitatively reveals that the presence of acetic acid not only accelerates the polymerization, but also suppresses H2S-catalyzed decomposition of NNTAs by decreasing the concentration of H2S dissolved in polar solvents. Benzoic acid is also able to promote the polymerization, while trifluoroacetic acid, phosphoric acid, and phenol are not appropriate promoters. The moderate acidity of acids is essential. l-Methionine, l-tryptophan, and l-phenylalanine, which are dissolved in DMF, initiate the controlled polymerization of sarcosine-NTA in the presence of acetic acid and introduce functional end groups to polysarcosines quantitatively. In DMAc, hydrophilic vancomycin is grafted by poly(N-butyl glycine). The amphiphilic product dissolves in dichloromethane and stabilizes water-in-oil emulsion.
研究领域:
高分子化学
·
材料科学
·
生物技术
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DOI
高影响因子
JOURNAL OF POLYMER SCIENCE
·
2021
·Vol. 59
·期 24
·3111-3121
·
IF 0
Xu Zhang,Wei Zhao,Chengliang Wang,Lan Cao,Qingfu Wang,Jingjiang Sun
In this work, a series of polyesters with different functional side groups were successfully prepared by Passerini three-component polymerization (P-3CP) in “one-pot” from biorenewable l -glutamic acid ( l -GA)-based monomers. First, the polymerization conditions including monomer feed ratios, solvents and comonomer were systematically studied using Boc-protected l -GA with adipaldehyde and tert -butyl isocyanide. Under the optimal polymerization conditions, a variety of N -substituted l -GA-based monomers as well as functional isocyanides were attempted in the P-3CP to produce polyesters with different functionalities. Moreover, it was found that after removal of pendant protecting groups, the obtained l -GA-based polyester degraded spontaneously into small molecules via 1,5-intramolecular cyclization between the pendant amine groups and the ester groups in polymer backbone. The structures and thermal properties of obtained polymers were determined by 1 H NMR, IR, SEC, MALDI-ToF-MS, DSC, and TGA measurements. Starting from biorenewable l -GA, this approach will provide a facile and straightforward route to produce functional and biodegradable polyesters, thus effectively expanding the range of biodegradable polymers. Graphical
研究领域:
材料科学
·
高分子化学
·
生物降解高分子
·
可持续化学
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DOI
危险品化学品经营许可证（带存储）