55030-23-4

Upstream product

• 64-04-0 phenethylamine 
• 621-82-9 Cinnamic acid 
• 859932-06-2 2-bromo-3-phenyl-propionic acid phenethylamide 
• 7664-41-7 ammonia 
• 102-92-1 cinnamoyl chloride 
• 104-55-2 3-phenyl-propenal 
• 1421426-92-7 N-phenethylcinnamimidoyl cyanide 
• 100-52-7 benzaldehyde 
• 140-10-3 (E)-3-phenylacrylic acid 
• 1943-82-4 phenethyl isocyanate 
• 30094-01-0 (E)-(2-phenylethenyl)magnesium bromide 
• 201230-82-2 carbon monoxide 
• 536-74-3 phenylacetylene 
• 23776-87-6 2,5‐dioxopyrrolidin‐1‐yl cinnamate 

Downstream Products

• 23020-04-4 N-phenethyl-3,3-diphenyl-propionamide 

Relevant academic research and scientific papers

Alpha-carbonyl alkenyl ester compound as well as preparation method and application thereof

The invention provides an alpha-carbonyl alkenyl ester compound and a preparation method thereof. The alpha-carbonyl alkenyl ester compound is also used for reacting with primary or secondary amine to prepare an amide compound. Two steps of reactions are combined to develop an amido bond and peptide bond forming method which takes carboxylic acid and amine as starting raw materials and allene ketone as a condensing agent. Meanwhile, the alpha-carbonyl alkenyl ester compound of the alpha-amino acid is used as a polypeptide synthesis building block for solid-phase synthesis of polypeptide. The method is mild in reaction condition, simple to operate and high in yield. Compared with an existing amido bond condensation reagent, allene ketone has the advantages of being easy and convenient to prepare, good in stability, small in molecular weight and free of racemization when alpha-chiral carboxylic acid is activated and the like. The compound is a novel amido bond and peptide bond condensation reagent.

Allenone-Mediated Racemization/Epimerization-Free Peptide Bond Formation and Its Application in Peptide Synthesis

Allenone has been identified as a highly effective peptide coupling reagent for the first time. The peptide bond was formed with an α-carbonyl vinyl ester as the key intermediate, the formation and subsequent aminolysis of which proceed spontaneously in a racemization-/epimerization-free manner. The allenone coupling reagent not only is effective for the synthesis of simple amides and dipeptides but is also amenable to peptide fragment condensation and solid-phase peptide synthesis (SPPS). The robustness of the allenone-mediated peptide bond formation was showcased incisively by the synthesis of carfilzomib, which involved a rare racemization-/epimerization-free N to C peptide elongation strategy. Furthermore, the successful synthesis of the model difficult peptide ACP (65-74) on a solid support suggested that this method was compatible with SPPS. This method combines the advantages of conventional active esters and coupling reagents, while overcoming the disadvantages of both strategies. Thus, this allenone-mediated peptide bond formation strategy represents a disruptive innovation in peptide synthesis.

Development of a triazinedione-based dehydrative condensing reagent containing 4-(dimethylamino)pyridine as an acyl transfer catalyst

A new triazinedione-based reagent, (N,N′-dialkyl)triazinedione-4-(dimethylamino)pyridine (ATD-DMAP) was developed for the operationally simple dehydrative condensation of carboxylic acids. This reagent comprises an ATD core and DMAP as the leaving group, which is liberated into the reaction system to accelerate acyl transfer reactions. Upon adding ATD-DMAP to a mixture of carboxylic acids and alcohols in the presence of an amine base, the corresponding esters were formed rapidly at room temperature. Moreover, dehydrative condensation between carboxylic acids and amines using ATD-DMAP proceeded in high yield.

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.

Method for click construction of amido bond by using pyrimidine condensing agent and application of amido bond in synthesis of amide and polypeptide

The invention discloses a method for click construction of an amido bond by using a pyrimidine condensing agent and an application of the amido bond in synthesis of amide and polypeptide. The amido bond construction method comprises the following steps: adding an organic solvent dissolved with organic alkali into a carboxylic acid component and an amine component, stirring for reaction, adding an organic solvent dissolved with a pyrimidine condensing agent, continuously stirring for reaction, concentrating, separating and purifying to obtain an amide or polypeptide product. According to the amido bond construction method, the use amount of the condensing agent is small, and the condensing agent is safe, odorless and easy to store and has good atom economy. The amido bond construction reaction time is only several seconds to ten minutes, and the amide or polypeptide synthesis time is greatly shortened. Besides, the amido bond construction reaction can also be quickly carried out in an organic phase-water phase biphasic system and in the organic phase-water phase biphasic system under the condition that alkali is not added, so that a mild and feasible path is provided for the amido bond construction reaction in an alkali-sensitive biological system.

Synthesis of zanthoxylamide protoalkaloids and their in silico ADME-Tox screening and in vivo toxicity assessment in zebrafish embryos

Inspired by the simple and attractive structure of zanthoxylamide protoalkaloids: armatamide, rubecenamide, lemairamin, rubemamine and zanthosine; isolated from plants of the genus Zanthoxylum. We report the synthesis of a series of 29 substituted N-pheny

An Efficient Solvent-Free Microwave-Assisted Synthesis of Cinnamamides by Amidation Reaction Using Phenylboronic Acid/Lewis Base Co-catalytic System

A microwave-assisted dehydrative amide condensation reaction is reported as an efficient access to cinnamamide derivatives under solvent-free conditions. This protocol between conjugated carboxylic acids and amines is based on the use of a co-catalytic system, including the presence of the commercially available phenylboronic acid and 4-(N, N-dimethylamino)pyridine N-oxide (DMAPO), with a complete chemoselectivity in favor of the corresponding α,β-unsaturated amides. The implementation of the reaction needs no special precaution, and less reactive amines, such as substituted anilines, are also efficient under these conditions. A series of novel conjugated amides have been evaluated for their cytotoxic activities against several human cancer cell lines.

Rapid access to cinnamamides and piper amides: Via three component coupling of arylaldehydes, amines, and Meldrum's acid

A practical method for the synthesis of cinnamamides and piper amides via a conceptually novel three component reaction of aldehydes, amines and Meldrum's acid has been reported. The reaction proceeds under operationally simple conditions without the aid of coupling reagents, oxidants, or catalysts, which are essential for the preparation of cinnamamides/piper amides via known methods. The formation of undesired chemical wastes that generally originate from the use of coupling reagents, oxidants, or catalysts has been avoided to make this reaction more atom economical.

Design, synthesis of N-phenethyl cinnamide derivatives and their biological activities for the treatment of Alzheimer's disease: Antioxidant, beta-amyloid disaggregating and rescue effects on memory loss

Gx-50 is a bioactive compound for the treatment of Alzheimer's disease (AD) found in Sichuan pepper (Zanthoxylum bungeanum). In order to find a stronger anti-AD lead compound, 20 gx-50 (1-20) analogs have been designed and synthesized, and their molecular structures were determined based on nuclear magnetic resonance (NMR) and mass spectrometry (MS) analysis, as well as comparison with literature data. Compounds 1-20 were evaluated for their anti-AD potential by using DPPH radical scavenging assay for considering their anti-oxidant activity, thioflavin T (ThT) fluorescence assay for considering the inhibitory or disaggregate potency of Ab, and transgenic Drosophila model assay for evaluating their rescue effect on memory loss. Finally, compound 13 was determined as a promising anti-AD candidate.