JOURNAL OF ORGANIC CHEMISTRY
·
2023
·
IF 3.6
Haiyun Peng,Yangyi Zhang,Guisheng Deng
Silver(I)-catalyzed tandem reaction of enynones with 4-alkenyl isoxazoles provides access to 2-(furan-2-yl)-1,2-dihydropyridines. No competitive cyclopropanation of alkenes and O–H insertion via (2-furyl)carbene complexes were observed. The cascade reaction proceeds via the formation of (2-furyl)metal carbene intermediate, the N–O bond cleavage of 4-alkenyl isoxazoles/rearrangement, subsequent 6π electrocyclic reaction, and [1,5] H-shift. The successive construction of both 1,2-dihydropyridine skeleton and furan frame has been achieved in the one-pot reaction. A broad range of readily available enynones and 4-alkenyl isoxazoles are suitable to this protocol; however, when R3 is the alkyl group such as n-Bu and Me, a complicated mixture was generated without the desired products. In addition, in the case of R4 = bulky group such as R3′SiOCH2, the reaction gave an in situ oxo-product of (2-furyl)silver carbene. An atom-economic strategy for the synthesis of 2-(furan-2-yl)-1,2-dihydropyridines has been established.
研究领域:
有机化学
·
合成化学
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DOI
PubMed
高影响因子
JOURNAL OF ORGANIC CHEMISTRY
·
2022
·
IF 4.198
Yueyue Zhu,Rupeng Dai,Chaoqun Huang,Wang Zhou,Xiaoyuan Zhang,Kundi Yang,Hongmei Wen,Wei Li,Jian Liu
In this study, we report a novel and efficient synthetic method to construct isoquinolone scaffold via the Rh(III)-catalyzed (4 + 2) annulation of benzamide with an unreported coupling reagent methyl 2-chloroacrylate. Accordingly, other valuable 1,2-benzothiazine and naphtho[1′,2′:4,5]imidazo[1,2-a]pyridine derivatives are also obtained through a similar synthetic protocol. Thus, our developed method is highlighted by high yield and reaction versatility.
研究领域:
有机化学
·
药物化学
✓ 已验证
DOI
高影响因子
JOURNAL OF APPLIED POLYMER SCIENCE
·
2020
·Vol. 138
·期 9
·49925
·
IF 2.52
Lei Ding,Yi Fan Chen,Zhengxiang Zhong,Fei Lu,Yunzhe Du,Li Liu,Yudong Huang
Polymers with high flexibility and high content renewable biomass materials have attracted particular attention. Plant-derived trans-cinnamic acid (CA) was introduced into the structure of epoxidized soybean oil to form trans-cinnamated epoxidized soybean oil (ESOCA). ESOCA with multi-cinnamate groups was cured via [2 + 2] cycloaddition photo-polymerization that with no need of photoinitiator, while acrylated epoxidized soybean oil (ESOAA) was photocured via free radical photopolymerization for comparison. The successful synthesis of ESOCA and ESOAA resin was proved by Fourier transform infrared, proton nuclear magnetic resonance, and gel permeation chromatography results. ESOCA is more environmentally friendly than ESOAA for that trans-CA volatility is much lower than acrylic acid during synthesis process. Notably, UV-cured ESOCA samples had a higher tensile strength at break and a 14.75 times elongation at break of that of UV-cured ESOAA samples, showing that [2 + 2] cycloaddition photo-polymerization is a good strategy to prepare flexible materials. Performances of ESOCA as coating on flexible PET film were also better than those of ESOAA, especially the flexibility, adhesion, and UV shielding performance. This study may open up a new way for design and synthesize flexible high performance polymer from renewable biomass materials.
研究领域:
材料科学
·
化学工程
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DOI
高影响因子
JOURNAL OF NANOPARTICLE RESEARCH
·
2017
·Vol. 19
·期 10
·1-12
·
IF 2.02
Tian Fei,Niu Libo,Chen Bo,Gao Xuejia,Lan Xingwang,Huo Li,Bai Guoyi
A novel magnetic core-shell nanocomposite Fe 3 O 4 @Chitosan@ZnO was successfully prepared by in situ chemical precipitation method. It has a clear core-shell structure with magnetic Fe 3 O 4 (about 160 nm in diameter) as core, chitosan as the inner shell, and ZnO as the outer shell, as demonstrated by the transmission electron microscopy and the related elemental mapping. Moreover, this nanocomposite has high magnetization (43.6 emu g −1 ) so that it can be easily separated from the reaction mixture within 4 s by an external magnetic field. The introduction of the natural chitosan shell, instead of the conventional SiO 2 shell, and its combination with the active ZnO ensures this novel nanocomposite green character and good catalytic performance in the synthesis of 2-benzimidazoles with moderate to excellent isolated yields at room temperature. Notably, it can be recycled seven times without appreciable loss of its initial catalytic activity, demonstrating its good stability and making it an attractive candidate for the green synthesis of 2-benzimidazoles.
A novel magnetic core-shell nanocomposite exhibited high activity and good stability in the green synthesis of 2-benzimidazoles under mild reaction conditions.
研究领域:
材料科学
·
纳米技术
·
催化
·
绿色化学
✓ 已验证
产品关联
DOI
高影响因子
SENSORS AND ACTUATORS B-CHEMICAL
·
2021
·
IF 7.46
Yujie Chen,Rui Sun,Wenhui Zhu,Zhen Zhang,Yali Chen,Shuo Wang,Qiliang Deng
Covalent organic frameworks (COFs) with predesigned bipyridine recognition sites (donated as BPD-COFs) were prepared by using 2, 2’-bipyridine-5, 5’-diamine and benzene-1, 3, 5-tricarbaldehyde as monomers, and the corresponding small molecule model compound (2, 2’-bipyridine-5, 5’-diiminebenzene, donated as BPDB) was synthesized by using benzaldehyde and 2, 2’-bipyridine-5, 5’-diamine. The fluorescence sensing property between BPD-COFs and BPDB were compared as the fluorescence sensing platform for the sensitive, selective and rapid detection of Ni 2+ . The unique structure characteristics such as large conjugated structure, high surface area, regularity pore canals and predesigned bipyridine link endow BPD-COFs with prominent fluorescence emission, enough space and strong specificity for Ni 2+ . The fluorescence quenching degree of BPD-COFs is four times more than that of BPDB. Besides better selectivity, BPD-COFs also displays the prominent advantages, such as the wider concentration range (4.20 × 10 −10 ∼1.26 × 10 -6 M) and lower limit of detection (6.80 × 10 -11 M) compared to that of BPDB (1.00 × 10 -7 ∼5.00 × 10 -7 M, 4.50 × 10 -8 M). Good spiked recoveries (>92.0 %) in chocolate and tea support that BPD-COFs is competent to detect Ni 2+ in real samples. All these results indicate that BPD-COFs is potential as a fast, sensitive, and accurate fluorescence sensing platform for the selective detection of Ni 2+ in complex system.
研究领域:
材料科学
·
分析化学
✓ 已验证
产品关联
DOI
高影响因子
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
✓ 已验证
DOI
PubMed
高影响因子
MOLECULES
·
2023
·Vol. 28
·期 4
·1930
·
IF 4.6
Yanqi Ban,Hui Wang,Zixuan Xiao,Lishui Sun,Qingyan Pan,Yingjie Zhao
A carbon–carbon-linked, ultrathin, two-dimensional (2D) polymer film was prepared at the air/water interface through photochemically triggered [2 + 2] cycloaddition. The preorganization of the monomers on the water surface and the subsequent photo-polymerization led to the successful preparation of the ultrathin 2D polymer film. The obtained film is continuous, free standing, and has a large area (over 50 μm2). Transmission electron microscopy (TEM) and atomic force microscopy (AFM) give clear evidence of the ultrathin film morphology. Raman spectroscopy and X-ray photoelectron spectroscopy (XPS) indicate successful photo-induced [2 + 2] polymerization.Keywords:two-dimensional polymers;covalent organic frameworks;porous materials;interfacial synthesis;[2 + 2] cycloaddition;photochemistry
研究领域:
材料科学
·
化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
GREEN CHEMISTRY
·
2015
·Vol. 17
·期 7
·3992-3999
·
IF 8.02
Shujing Zhu,Xiaoqiang Ma,Erzheng Su,Dongzhi Wei
From an environmental perspective, utilizing nonconventional solvents (i.e. green solvents) with low ecological footprints is a highly beneficial alternative to using conventional organic solvents to form a reaction system. The nitrile hydratase (NHase, EC 4.2.1.84) catalyzed hydration of 2-amino-2,3-dimethylbutyronitrile (ADBN) to 2-amino-2,3-dimethylbutyramide (ADBA) in various green solvent–aqueous reaction systems was investigated in this study. After systematically optimizing the reaction conditions, the HFE-7100/H2O (v/v, 10%) biphasic system was ultimately identified as a promising reaction system for reducing product inhibition, avoiding substrate hydrolysis, and facilitating product separation and solvent recovery. The average ADBA yield of an entire batch reaction was 97.3%, which is obviously higher than those obtained with previously reported chemical or enzymatic methods. This is the first attempt to apply a fluorous solvent–aqueous biphasic system to a biocatalytic process, and the results suggest that the fluorous solvent employed in the biphasic system satisfies the requirements for green chemistry.
研究领域:
生物化学
·
环境科学
·
绿色化学
✓ 已验证
DOI
高影响因子
FITOTERAPIA
·
2024
·
IF 2.5
Yuan Wei,Wen-Hua Dong,Wei Li,Jun Zeng,Hui-Qin Chen,Sheng-Zhuo Huang,Li Yang,Wen-Li Mei,Ya-Li Wang,Zhi-Yong Guo,Hao-Fu Dai,Hao Wang
Six new dimeric 2-(2-phenylethyl)chromones ( 1 – 6 ) were successfully isolated from the ethanol extract of agarwood of Aquilaria filaria from Philippines under HPLC-MS guidance. Compounds 1 – 6 are all dimers formed by linking 5,6,7,8-tetrahydro-2-(2-phenylethyl)chromone and flindersia 2-(2-phenylethyl)chromone via a single ether bond, and the linkage site (C5-O-C8′′) of compound 2 is extremely rare. A variety of spectroscopic methods were used to ascertain their structures, including extensive 1D and 2D NMR spectroscopic analysis, HRESIMS, and comparison with literature. The in vitro tyrosinase inhibitory and anti-inflammatory activities of each isolate were assessed. Among these compounds, compound 2 had a tyrosinase inhibition effect with an IC 50 value of 27.71 ± 2.60 μM, and compound 4 exhibited moderate inhibition of nitric oxide production in lipopolysaccharide-stimulated RAW264.7 cells with an IC 50 value of 35.40 ± 1.04 μM.
研究领域:
植物化学
·
药理学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
JOURNAL OF MOLECULAR STRUCTURE
·
2021
·
IF 3.196
Xingjun Gao,Yuting Zhang,Qianqian Xie,Weiqiang Xu,Shouwen Jin,Qinqin Ye,Yi Yu,Bin Chen,Hui Liu,Daqi Wang
Cocrystallization of 2-aminobenzothiazole/2-aminothiazole with a set of organic acids got a total of 11 crystalline adducts with the compositions: (2-aminobenzothiazole): (saccharin) [(HL1) + • (sac) − , sac = saccharinate] (1) , (2-aminobenzothiazole): (dichloroacetic acid) [(HL1) + • (dca) − , dca = dichloroacetate] (2) , (2-aminobenzothiazole): (trichloroacetic acid) [(HL1) + • (tca) − , tca = trichloroacetate] (3) , (2-aminothiazole): (glycolic acid) [(HL2) + • (gla) − , gla = glycolate] (4) , (2-aminothiazole): (2-methyl-2-phenoxypropanoic acid) [(HL2) • (mppa), mppa = 2-methyl-2-phenoxypropanoiate] (5) , (2-aminothiazole): ((2,4-dichlorophenoxy)-acetic acid) [(HL2) • (dcpa), dcpa = (2,4-dichlorophenoxy)-acetate] (6) , (2-aminobenzothiazole) 2 : (2,3-dibromo-butanedioic acid) 2 [(HL1) 2 + • (dba) 2- • (H 2 dba), dba = 2,3-dibromo-butanedioate] (7) , (2-aminothiazole): (1,4-cyclohexanedicarboxylic acid) [(L2) 2 • (1,4-H 2 cha), 1,4-H 2 cha = 1,4-cyclohexanedicarboxylic acid] (8) , (2-aminothiazole): (4-nitrophthalic acid) [(HL2 + ) • (4-Hnpa − ), Hnpa − = 4-nitro hydrogenphthalate] (9) , (2-aminothiazole): (5-hydroxyisophthalic acid) [(HL2 + ) • (5-Hipta − ), 5-Hipta − = 5-hydroxy hydrogenisophthalate] (10) and (2-aminobenzothiazole): (3-nitrophthalic acid): CH 3 CH 2 OH [(HL1) • (3-Hnpa − ) • CH 3 CH 2 OH, 3-Hnpa − = hydrogen 3-nitrophthalate] (11) . These adducts have been examined by XRD, IR and elemental analysis and the melting points were also gauged. Their structural and supramolecular aspects are fully analyzed. The result unveils that among the investigated crystalline solids 1 - 7 and 9 - 11 the aryl N in thiazole moieties are protonated when the organic acids are deprotonated, the crystal packing is ruled by the strong charge-assisted N-H⋯O H-bond from the NH + and the deprotonated acids. 8 is a cocrystal sustained by the neutral N-H⋯O/O-H⋯N H-bonds. Except the N-H⋯O H-bonds, the O-H•••O H-bonds were also found at 4, 7 and 9 - 11. 1 has the additional N-H•••S/N-H•••N H-bonds. The N-H•••Cl H-bond was appeared in 3 . Further analysis of the crystal packing told that a different set of additional CH 2 -C, CH-O/CH 2 -O, CH-S, CH-CH, CH-Cl, Cl-Cl, Cl-S, Br-S, Br-π, CH-π/CH 2 -π/CH 3 -π, N-π, C-S, O-C π , O-N, O-O, O-S, π-π and O-π contacts contribute to the stabilization and expansion of the total structures. For the interplay of the various weak nonbonding interactions these structures adopted homo or hetero supramolecular synthons or both. The recognition of the base-acid created the classical R 2 2 (8) synthon in all compounds except 7 . For the cooperation of these weak bonds, 1D-3D structures were made.
研究领域:
化学
·
晶体学
·
超分子化学
✓ 已验证
DOI
高影响因子
CHINESE JOURNAL OF CHEMICAL PHYSICS
·
2019
·Vol. 32
·期 3
·306-312
·
IF 0.791
Yu Ye-peng,Li Zhao-hui,Lin Xuan,Chen Jun,Zhang Hang,Li Yan-bo,Wang Huang-huang,Sun Rui-rui,Meng Qing-hui,Shan Xiao-bin,Liu Fu-yi,Sheng Liu-si
The photoionization and dissociation of 2-methyl-2-propen-1-ol (MPO) have been investigated by using molecular beam experimental apparatus with tunable vacuum ultraviolet synchrotron radiation in the photon energy region of 8.0–15.5 eV. The photoionization efficiency (PIE) curves for molecule ion and fragment ions: C 4 H 8 O + , C 4 H 7 O + , C 3 H 5 O + , C 4 H 7 + , C 4 H 6 + , C 4 H 5 + , C 2 H 4 O + , C 2 H 3 O + , C 3 H 6 + , C 3 H 5 + , C 3 H 3 + , CH 3 O + , CHO + have been measured, and the ionization energy (IE) and the appearance energies (AEs) of the fragment ions have been obtained. The stable species and the first order saddle points have been calculated on the CCSD(T)/cc-pvTZ//B3LYP/6-31+G(d,p) level. With com-bination of theoretical and experimental results, the dissociative photoionization pathways of 2-methyl-2-propen-1-ol are proposed. Hydrogen migrations within the molecule are the dominant processes in most of the fragmentation pathways of MPO.
研究领域:
化学物理学
·
分子光谱学
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产品关联
DOI
高影响因子
JOURNAL OF CHEMICAL AND ENGINEERING DATA
·
2020
·
IF 2.369
Xuemei Zhang,Xiaojie Yang,Jie Jian,Chungui Jian,Jie He,Hongwei Wang,Wangxin Kong,Guangjin Shangguan,Meifang Xia
Liquid–liquid equilibrium (LLE) data of the ternary system 2-methyl-2-butanol + water + o-xylene were determined at 303.2, 313.2, and 323.2 K under 101.3 kPa. The extraction capacity of o-xylene is expressed by selectivity, which is more than 118 and decreases with the increase of temperature. The quality of the experimental LLE data is verified by calculation of the overall mass balance and alignment between the conjugated phases and overall compositions. The experimental LLE data were regressed by the NRTL and UNIQUAC models, and the binary interaction parameters were obtained. And the root-mean-square deviations (RMSDs) are less than 1.02%.
研究领域:
化学工程
·
物理化学
✓ 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）