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A facile transformation of alkynes into α-amino ketones by an N-bromosuccinimide-mediated one-pot strategy

Chinese Chemical Letters 2019年第2期30卷 383-385页

作者： Ting Wei Yongming Zeng Wei He Lili Geng Liang Hong Department of Chemistry and Applied Chemistry Changji University State Key Laboratory of Coordination Chemistry Nanjing University

A facile transformation of alkynes into α-amino ketones by an N-bromosuccinimide-mediated one-pot cascade strategy is described. A variety of α-amino ketones are obtained in moderate to good yields under mild conditions. To overcome the multi-step synthesis, N-bromosuccinimide is involved in multiple tasks, playing a key role in the reaction course.

关键词： α-amino ketones N-Bromosuccinimide Alkynes One-pot synthesis

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Thermodynamic solvation of a series of homologous α-amino acids in non-aqueous mixture of ethylene-glycol and N,N-dimethyl formamide

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Journal of Biophysical Chemistry 2011年第3期2卷 185-193页

作者： Kalachand Mahali Sanjay Roy Bijoy Krishna Dolui Dept. of Chemistry Shibpur Dinabundhoo Institution(College) Howrah India

Standard free energies (ΔG0t(i) ) and entropies (ΔS0t(i)) of transfer of some homologous α-amino acids viz. glycine (gly), dl-alanine (ala), dl-α-amino butyric acid (aba) and dl-nor-valine (nor-val) from protic ethylene glycol (EG) to dipolar aprotic N,N-dimethyl formamide (DMF) have been evaluated from solubility measure-ments at five equidistant temperatures i.e from 15 to 350C. The observed ΔG0t(i) and TΔS0t(i) Vs composition profiles are complicated because of the various interaction effects. The chemical effects of the transfer Gibbs energies (Δ***(i)) and entropies of transfer (Δ***(i)) have been obtained after elimination of cavity effect, estimated by the scaled particle theory and dipole-dipole interaction effects, estimated by the use of Keesom-orientation expression. The chemical contributions of transfer energetics of homologous α-amino acids are guided by the composite effects of increased dispersion interaction, basicity and decreased acidity, hydrogen bonding effects and solvophobic solvation of ethylene glycol and N, N-dimethyl formamide mixed solvent as compared to that of reference solvent (ethylene glycol).

关键词： Non-Aqueous Solvent System Transfer Energetic Zwitterions α-amino Acids Solvophobic Solvation

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Development of <i>α</i>-amino Acid Detection with Peroxyoxalate Chemiluminescence by Using Water-Acetonitrile-Ethyl Acetate Mixed Solution

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American Journal of Analytical Chemistry 2020年第1期11卷 15-24页

作者： Hyo Kan Ryo Mizutani Kazuhiko Tsukagoshi Department of Chemical Engineering and Materials Science Faculty of Science and Engineering Doshisha University Kyotanabe Japan Bio-Microfluidic Science Research Center Doshisha University Kyotanabe Japan

Peroxyoxalate chemiluminescence was, for the first time, examined by using ternary mixed solutions of water-hydrophilic/hydrophobic organic solvent. Eosin Y as a model fluorescence compound was dissolved with the ternary solutions of water (1.0 mM carbonate buffer, pH 9.0)-acetonitrile-ethyl acetate, water-rich of 15:3:2 volume ratio and organic solvent-rich of 3:8:4 volume ratio, to which bis(2,4,6-trichlorophenyl) oxalate and hydrogen peroxide chemiluminescence reagent were added. The chemiluminescence observed with the ternary solutions, especially the organic solvent-rich solution, showed a larger signal than that observed with the water only solution or water-acetonitrile mixed solution. Chemiluminescence in the presence of twenty types of α-amino acid was similarly examined by using the ternary organic solvent-rich solution. The chemiluminescence of three α-amino acids with fluorescence properties was enhanced with the ternary solution. The data reported here may contribute to development of a new, sensitive peroxyoxalate chemiluminescence detection system.

关键词： Peroxyoxalate chemiluminescence α-amino Acids Water-Acetonitrile-Ethyl Acetate Bis(2 4 6-Trichlorophenyl) Oxalate

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Application of modified amino acid as a chiral building block in asymmetric synthesis

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Chinese Science Bulletin 2001年第23期46卷 1952-1956页

作者： WANG Jianping ZHANG Xiyun CHEN Qinghua Department of Chemistry Beijing Normal UniversityBeijing 100875China Department of Chemistry Luoyang Teacher’s CollegeLuoyang 471022China

Phenylglycine 1 as a representative of natural resourceful a-amino acid was modified by reduction and protection of functional group to afford the amino alcohol as a chiral building block 3. A new chiral compound, the chiral building block/spiro-cyclopropane derivative containing four stereogenic centers, compound 7, has been obtained in 52% yield with de≥98% via the tandem double Michael addition/internal nucleophilic substitution under mild condition of 5-l-menthyloxy-3-bromo-2-(5H)-furanone 4 with the nucleophilic reagent, the amino alcohol 3. The new chiral compound 7 is identified on the basis of its analytical data and spectroscopic data, such as UV, IR, 1H NMR, 13C NMR, MS and elementary analysis. The absolute configuration of the interesting spiro-cyclopropanes 7 was established by X-ray crystallography. This result can provide new route and method for the introduction of chiral building block and the important synthetic strategy in synthesis of some complex molecules containing

关键词： modified α-amino acid phenylglycine amino alcohol chiral building block spiro-cyclopropane derivative stereochemistry and absolute configuration.

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Chiral assembly of achiral pseudoisocyanine with D-and L-phenylalanine

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Science China Chemistry 2009年第8期52卷 1227-1234页

作者： ZENG LiXi HE YuJian DAI ZhiFeng WANG Jian WANG CaiQi YANG YongGang College of Chemistry and Chemical Engineering Graduate University of Chinese Academy of SciencesBeijing 100049China State Key Laboratory of Natural and Biomimetic Drugs Peking UniversityBeijing 100191China Key Laboratory of Organic Synthesis of Jiangsu Province College of ChemistryChemical Engineering and Materials ScienceSoochow(Suzhou)UniversitySuzhou 215123China

Supramolecular chirality and molecular self-assembly are important and interesting phenomena in living and non-living *** this work,supramolecular chirality of achiral pseudoisocyanine(PIC) J-aggregates was successfully induced by D-,L-phenylalanine(Phe) and other amino acids in NaCl *** chiral J-aggregates showed a characteristic,induced circular dichroism(ICD) in the visible region of J-band chromophore which depends on the absolute configuration,concentration and side groups of α-amino acids,as well as *** atomic force microscopy images indicated that the J-aggregates exist in large bundles of entangled nanofibers,and the observed ICD might result from the macroscopic helical arrangement of the assemblies.

关键词： supramolecular chirality pseudoisocyanine self-assembly induced circular dichroism α-amino acid

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Synthetic Approach for Novel Fluorine Substituted <i>α</i>-aminophosphonic Acids Containing 1,2,4-Triazin-5-One Moiety as Antioxidant Agents

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International Journal of Organic Chemistry 2018年第1期8卷 1-15页

作者： Mohammed S. T. Makki Reda M. Abdel-Rahman Abdulrahman S. Alharbi Department of Chemistry Faculty of Science King Abdul Aziz University Jeddah KSA

Novel fluorine substituted α-amino phosphonic acids containing 1,2,4-triazin- 5-one (6a-f) have been obtained from fluoroacylation of 6-(2′-amino-5′-nitrophenyl)-3-thioxo-1,2,4-triazin-5(4H)-one (1) followed by ammonilysis to give the corresponding 3-amino-derivative 3. Condensation of compound 3 with nitro/halogenated aromatic aldehydes yielded the Schiff bases 4. The simple addition of diethyl phosphonate to compound 4 produced the α-amino phosphonates 5. Acidic hydrolysis of compound 5 produced the fluorine substituted α-amino acids derivatives 6. Structures of the new compounds have been established with the help of elemental analysis and spectral measurements. Also, the products evaluated as antioxidants, where the fluorinated α-amino phosphonic acids 6 are more active than the other synthesized systems.

关键词： Synthetic Fluorine α-amino Acids 1 2 4-Triazin-5-One Moiety Antioxidants Activity

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