JOURNAL OF CHEMICAL AND ENGINEERING DATA
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2021
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IF 2.694
Zilong Cui,Jingling Ye,Liang Yao,Zhi Wang,Ting Wang,Yonghong Hu
In this study, the data on solid–liquid equilibrium of l-prolinamide were studied using the gravimetric method. The solubility of l-prolinamide was measured in ten pure solvents (tetrahydrofuran, n-heptane, n-propanol, acetone, acetonitrile, ethyl acetate, N,N-dimethylformamide, n-hexane, cyclohexane, and isopropanol) and three binary solvent mixtures(ethyl acetate + tetrahydrofuran, n-heptane + ethyl acetate, and n-hexane + acetone) in the temperature range of 278.15–323.15 K at atmospheric pressure. The experimental values showed that the solubility increased with the increase of temperature in all solvents. The solubility data in different pure solvents were fitted using the modified Apelblat model and the Buchowski–Ksiazaczak λh model. For the solubility data of three binary solvent mixtures, the modified Apelblat model, the combined nearly ideal binary solvent/Redlich–Kister (CNIBS/R–K) model, and the Jouyban–Acree model were used to fit. In all four models, the modified Apelblat model had a better correlation with the solubility of l-prolinamide weather in pure solvents or binary solvent mixtures. The experimental results showed that n-heptane and n-hexane could be used as antisolvents, which could be used in the purification process of l-prolinamide and guide the large-scale production of many drugs such as Alpelisib in industries.
研究领域:
化学工程
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药物化学
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DOI
高影响因子
NEW JOURNAL OF CHEMISTRY
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2025
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IF 2.5
Xiong-Li Liu,Jing Lou,Xian-Qiao Zhu,Di-Cheng Pan,De-Wu Liu,Hui-Xian Jing,Wenjing Zhang,Hong-Xing Cen,Guo-Deng Guo-Deng Dong
The development of single chiral source-derived ligands to fine-switch enantioselectivity has continuously attracted the attention in asymmetric catalysis. Herein, we use the same chiral source L-prolinamide as the starting material, synthesizing chiral bidentate pyridine-type N-oxide ligands (denoted as Py-NO) and chiral monodentate phenyl N-oxide ligands (denoted as Ph-NO); their effectiveness was demonstrated in the switch of enantioselectivity in palladium(II)-catalysed Friedel-Crafts (FC) alkylation of indoles and 2,3-dioxopyrrolidines, and both enantiomers of structurally important indole derivatives can be prepared in good yields (up to 91% yield) and high enantioselectivities (up to 99% ee). Key to the success of switch of enantioselectivity is the existence of two different activation patterns in this palladium(II) catalytic system. Experiments demonstrated that a counteranion would plausibly coordinate to the palladium(II) center in the stereoselectivity-determining step. Preliminary mechanistic studies provide a rational explanation for the above observations. This study was the first example of monodentate ligand in asymmetric catalytic Friedel-Crafts alkylation.
研究领域:
不对称催化
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有机合成
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配位化学
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对映选择性化学
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产品关联
DOI
高影响因子
CRYSTAL GROWTH & DESIGN
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2025
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IF 3.4
Detao Li,Zichen Ning,Feiqiang He,Zhi Gao,Limin Zhou,Li Xu,Zhijian Zheng,Jerry Heng,Shichao Du,Jinbo Ouyang
To enable efficient separation of chiral drugs and enhance their practical utility, this study investigates cocrystallization as a novel separation and purification strategy. Using R/S-mandelic acid and d/l-prolinamide as model compounds, we screened potential cocrystal/salt coformers and successfully synthesized seven novel chiral salts. The proton transfer was elucidated by analyzing molecular electrostatic potential differences at the hydrogen-bonding sites. Moreover, the formation mechanism of salts was explored through structural analyses, such as Hirshfeld surface calculations, energy framework assessments, and crystal void analysis. Considering the distinct properties of various chiral salts, we conducted competitive cocrystallization experiments, establishing a complementary chiral pairing principle that provides a theoretical foundation for cocrystallization-based chiral resolution. Based on these findings, we developed multiple processes for the separation of R- and S-mandelic acid as well as l- and d-prolinamide, achieving product purities exceeding 80%, which strongly demonstrate the feasibility of cocrystallization separation technology for chiral resolution. This work not only introduces a groundbreaking approach to chiral separation but also highlights the vast potential of cocrystallization technology in pharmaceutical purification and beyond.
研究领域:
药物化学
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晶体工程
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手性分离技术
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超分子化学
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材料科学
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产品关联
DOI
高影响因子
LANGMUIR
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2020
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IF 3.557
Xuejiao Yang,Liwei Zhang,Yaoyu Liang,Yuefei Wang,Yuhe Shen,Qiguo Xing,Wei Qi,Pengfei Wang,Xiao Liu,Mengyao Yang,Rongxin Su,Mingxia He,Zhimin He
Supramolecular nanocatalysts were designed for asymmetric reactions through the self-assembly process of a bio-organometallic molecule, ferrocene-l-prolinamide (Fc-CO-NH-P). Fc-CO-NH-P could self-assemble into versatile nanostructures in water, including nanospheres, nanosheets, nanoflowers, and pieces. In particular, the self-assembled nanoflowers exhibited a superior specific surface area, high stability, and delicate three-dimensional (3D) chiral catalytic active sites. The nanoflowers could serve as heterogeneous catalysts with an excellent catalytic performance toward direct aldol reactions in aqueous solution, achieving both high yield (>99%) and stereoselectivity (anti/syn = 97:3, ee% >99%). This study proposed a significant strategy to fabricate supramolecular chiral catalysts, serving as a favorable template for designing new asymmetric catalysts.
研究领域:
化学
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材料科学
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催化领域
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产品关联
DOI
PubMed
高影响因子
TALANTA
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2017
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IF 4.162
Junfang Jiang,Xiaoyu Mu,Juan Qiao,Yuan Su,Li Qi
Using chiral amino amide ionic liquids as the ligands, a new chiral ligand exchange capillary electrophoresis method with Cu(II) as the central ion was constructed for enantioseparation of labeled D,L-amino acids. The effects of key parameters, including pH value of the running buffer, the ratio of Cu(II) to chiral amino amide ionic liquids, the concentration of complexes based on Cu(II)-chiral amino amide ionic liquids were investigated. It has been observed that eight pairs of labeled D,L-amino acids could be baseline-separated with a running buffer of 15.0 mM ammonium acetate , 10.0 mM Cu(II) and 20.0 mM L-phenylalaninamide based ionic liquid at pH 5.0. The quantitation of D,L-amino acids was conducted and good linearity (r 2 ≥ 0.964) was obtained. Furthermore, an assay for determining the enantiomeric purity of D,L-amino acids was developed and the possible enantiorecognition mechanism was discussed briefly. The results indicated that the chiral amino amide ionic liquids could play the role of ligands in chiral ligand exchange capillary electrophoresis system and exhibit great potential in chiral analysis.
研究领域:
分析化学
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手性分离技术
✓ 已验证
产品关联
DOI
PubMed
高影响因子
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