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• 76071-79-9 2-Phenylethynyl-4,5-dihydro-oxazole 

Relevant academic research and scientific papers

Water-soluble alkyne amide condensing agent as well as preparation method and application thereof

The invention discloses a water-soluble alkyne amide condensing agent and an application method of the water-soluble alkyne amide condensing agent in synthesis of amide, polypeptide, ester and thioester compounds. The alkyne amide condensing agent has good performance and can efficiently and conveniently promote formation of amide bonds and ester bonds, alpha-chiral centers of carboxylic acid is free of racemization in the reaction process, carboxylic acid activation and a subsequent amidation reaction can be performed spontaneously, and extra additives and catalysts are not needed. After amidation and esterification reactions are finished, reaction by-products and the excessive alkyne amide condensing agent can be converted into substances capable of being dissolved in water through treatment by a weakly-acidic aqueous solution, and then high-purity products can be obtained through extraction and/or recrystallization. The whole process is simple to operate, has the characteristics ofconvenience in purification, wide application range, economic performance and environmental protection, conforms to the direction of green chemistry in modernization, and has good application prospects.

Water-removable ynamide coupling reagent for racemization-free syntheses of peptides, amides, and esters

A novel ynamide coupling reagent, the by-product of which can be removed by water, was reported. It promotes the direct coupling between carboxylic acids and amines, alcohols or thiols to provide amides, peptides, esters and thioesters, respectively. No detectable racemization was observed for all the coupling reactions of carboxylic acids containing an α-chiral center. Importantly, a simple acidic aqueous work-up removed the by-product readily to afford pure coupling products in good to excellent yields without the use of column chromatography, thus making this method more environmentally benign, user friendly and cost-effective. The robustness of the water-removable ynamide coupling reagent was further exemplified by the racemization/epimerization-free synthesis of carfilzomib, in which no column chromatography purification was involved for the entire 12-step synthesis.

N-triflyl-propiolamides: Preparation and transamidation reactions

N-Trifluoromethylsulfonyl-propiolamides have been prepared by two methods: a) N-triflation of secondary acetylenic carboxanilides, prepared in two steps from terminal alkynes, with triflic anhydride (Tf2O) and b) from terminal alkynes and an aryl or alkyl isocyanate followed by Tf2O in a consecutive one-pot reaction. The title compounds are bench-stable and insensitive to water and alcohols but amenable to transamidation reactions with a wide range of amine nucleophiles. Conversely, they are excellent reagents for the propynoylation of ammonia, primary and secondary amines, anilines, and hydrazines.

Mild and efficient preparation method of alpha-acyloxy alkenyl amide compound and application thereof to synthesis of amide and polypeptide

The invention discloses a mild and efficient preparation method of an alpha-acyloxy alkenyl amide compound and application thereof to synthesis of an amide and a polypeptide. The alpha-acyloxy alkenyl amide compound is obtained by an addition reaction of alkyne amide and carboxylic acid in dichloromethane under a condition that the temperature is 0 to 50 DEG C; the product alpha-acyloxy alkenyl amide compound can generate the amide or the polypeptide with amides through combination reaction; the two reactions can be carried out step by step and can also be carried out in one pot; when the two reactions are carried out in one pot, the product alpha-acyloxy alkenyl amide compound does not need to be purified from the former reaction and the amide compound is directly added to react, wherein in the reaction of generating the amide or the polypeptide, a solvent can also be water, so that a novel method for fixed-site decoration and marking of biological macromolecules including proteins, nucleic acid and the like in a water phase is provided. The mild and efficient preparation method has moderate reaction conditions and does not need a metal catalyst; when the carboxylic acid, which has chirality on an alpha site of carboxyl, forms an amide bond or a peptide bond, no racemization occurs; the mild and efficient preparation method is simple to operate and wide in application range.

Ynamides as Racemization-Free Coupling Reagents for Amide and Peptide Synthesis

A highly efficient, two-step, one-pot synthetic strategy for amides and peptides was developed by employing ynamides as novel coupling reagents under extremely mild reaction conditions. The ynamides not only are effective for simple amide and dipeptide synthesis but can also be used for peptide segment condensation. Importantly, no racemization was detected during the activation of chiral carboxylic acids. Excellent amidation selectivity toward amino groups in the presence of -OH, -SH, -CONH2, ArNH2, and the NH of indole was observed, making the protection of these functional groups unnecessary in amide and peptide synthesis.

Ranging correlated motion (1.5 nm) of two coaxially arranged rotors mediated by helix inversion of a supramolecular transmitter

For a long-range transmission of motion between two movable parts apart from each other, transmitters that can precisely correlate these two motions should be properly incorporated into the system. However, such a motional relay is yet to be realized in a

Electrostatically controlled hierarchical arrangement of monocationic silver(I) and dicationic mercury(II) ions between disk-shaped template ligands

This paper describes hierarchical arrangement of three Ag+ and three Hg2+ ions using two disk-shaped hexa-monodentate template ligands in which three oxazolyl rings are arranged each on the two concentric circles. The hierarchical manner of ligand arrangement allows the selective binding of monocationic Ag+ and dicationic Hg2+ ions to the inner first and the outer second generation coordination sites, respectively. This hierarchically well-balanced metal assembly should arise primarily from a minimized electrostatic repulsion between positively charged six metal ions arranged within the heteronuclear complex. Copyright