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JOURNAL OF CHROMATOGRAPHY A · 2013 · IF 4.612

Novel chiral core–shell silica microspheres with trans-(1R,2R)-diaminocyclohexane bridged in the mesoporous shell: Synthesis, characterization and application in high performance liquid chromatography

Xiabing Wu,Linjun You,Bin Di,Weiqiang Hao,Mengxiang Su,Yu Gu,Lingling Shen

Novel chiral core–shell silica microspheres with trans -(1 R ,2 R )-diaminocyclohexane (DACH) moiety bridged in the mesoporous shell were synthesized using layer-by-layer method. The chiral mesoporous shell around the nonporous silica core was formed by the co-condensation of N , N ′- bis -[(triethoxysilyl)propyl]- trans -(1 R ,2 R )- bis -(ureido)-cyclohexane (DACH-BS) and tetraethoxysilane (TEOS) using octadecyltrimethylammonium chloride (C 18 TMACl) and triblock poly(ethylene oxide)-b-poly(propylene oxide)-b-poly(ethylene oxide) copolymer (P123) as the templates. The functionalized core–shell silica microspheres were characterized and tested as chiral stationary phases for high performance liquid chromatography (HPLC). R / S -1,1′-bi-2,2′-naphthol, R / S -6,6′-dibromo-1,1′-bi-2-naphthol and R / S -1,1′-bi-2,2′-phenanthrol were enantioseparated rapidly on the column packed with the DACH core–shell silica particles. Moreover, the column packed with core–shell particles exhibited better performance than the column packed with the DACH functionalized periodic mesoporous organosilicas.

CAS / MDL: 24801-88-5
研究领域: 材料科学 · 分析化学
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ACS Nano · 2023 · IF 17.1

Single-Molecule Interconversion between Chiral Configurations of Boronate Esters Observed in a Nanoreactor

Xiaoyu Du,Shanyu Zhang,Liying Wang,Yuqin Wang,Pingping Fan,Wendong Jia,Panke Zhang,Shuo Huang

Isomers of some chemical compounds may be dynamically interconvertible. Due to a lack of sensing methods with a sufficient resolution, however, direct monitoring of such processes can be difficult. Engineered Mycobacterium smegmatis porin A (MspA) nanopores can be applied as nanoreactors so that chemical reactions can be directly monitored. Here, an MspA modified with a phenylboronic acid (PBA) adapter was prepared and was used to observe dynamic interconversion between chiral configurations of boronate esters, which appears as telegraphic switching on top of nanopore events. The mechanism of this behavior was further confirmed by trials with different halogenated catechols, dopamine, adenosine, 1,2-propanediol, and (2R,3R)-2,3-butanediol, and its generality has been demonstrated. These results suggest that an engineered MspA possesses an exceptional resolution in its monitoring of chemical reaction processes and may inspire the future design of nanopore small-molecule sensors.

研究领域: 纳米技术 · 化学生物学 · 分析化学 · 分子生物学
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RUSSIAN JOURNAL OF ORGANIC CHEMISTRY · 2024 ·Vol. 60 ·期 10 ·1999-2003 · IF 0.8

Synthesis of (S)-2-{(R)-Hydroxy[2-(trifluoromethyl)phenyl]­methyl}cyclohexan-1-one Using (1R,2R)-2-(Piperidin-1-yl)­cyclohexan-1-amine as a Catalyst

Li C. L.,Wang S. Y.,Zhan M. R.,Chen C. C.,Wang Z. X.

Chiral monosubstituted cyclohexanediamine catalyst, namely (1 R ,2 R )-2-(piperidin-1-yl)cyclo­hexan-1-amine ( Cat1 ) has been efficiently synthesized and used to catalyze the aldol reaction of cyclohexanone and 2-(trifluoromethyl)benzaldehyde to obtain ( R )-2-{( S )-hydroxy[2-(trifluoromethyl)phenyl]methyl}cyclo­hexan-1-one. The catalyst (20 mol %) provided high yield (up to 85%) and excellent enantioselectivity (95.6% ee ) in water solution in three parallel tests.

研究领域: 有机化学 · 催化化学
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JOURNAL OF CHEMICAL THERMODYNAMICS · 2018 · IF 2.631

Measurement and thermodynamic modelling of ternary liquid-liquid equilibrium for extraction of (1R,2R)-(−)-1,2-Diaminocyclohexane from aqueous solution with C4–C5 alcohols at different temperatures

Huanxin Li,Junwei Zhang,Yonghui Dou,Li Xu,Guoji Liu

(Liquid + liquid) equilibrium data for the ternary systems of {(2-Methyl-1-propanol or 3-Methyl-1-butanol) + (1 R ,2 R )-(−)-1,2-Diaminocyclohexane + water} were measured at (288.2–318.2) K under atmospheric pressure. The Othmer-Tobias and Hand equations were employed to verify the reliability of the experimental data. Besides, the distribution coefficients and selectivity factors calculated from the experimental tie-line data were applied to evaluate the extraction performance of separating (1 R ,2 R )-(−)-1,2-Diaminocyclohexane from aqueous solution and 3-Methyl-1-butanol was proved to be very promising. Furthermore, the binary interaction parameter values were obtained by correlating the experimental data with NRTL and UNIQUAC models. All the RMSD values were less than 0.0184, indicating that both models can be used to describe the liquid-liquid equilibrium behaviour of the studied systems.

CAS / MDL: 20439-47-8 123-51-3
研究领域: 化学工程 · 热力学
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