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Upstream product

• 10029-04-6 ethyl 2-(hydroxymethyl)acrylate 
• 98-88-4 benzoyl chloride 
• 65-85-0 benzoic acid 
• 17435-72-2 ethyl 2-bromomethyl-2-propenoate 
• 140-88-5 ethyl acrylate 

Downstream Products

• 1234706-21-8 (S)-1-tert-butyl 5-ethyl 2-(diphenylmethylene-amino)-4-methylenepentanedioate 

Relevant academic research and scientific papers

Silver-catalyzed decarboxylative radical allylation of α,α-difluoroarylacetic acids for the construction of CF2-allyl bonds

An efficient silver-catalyzed method of decarboxylative radical allylation of α,α-difluoroarylacetic acids to build CF2-allyl bonds has been developed. Using allylsulfone as an allyl donor, α,α-difluorine substituted arylacetic acids bearing various functional groups are successfully allylated to access a series of 3-(α,α-difluorobenzyl)-1-propylene compounds in moderate to excellent yields in aqueous CH3CN solution under the mild conditions. Experimental studies disclosed that the α-fluorine substitution of arylacetic acid has a great influence on free radical activity and reactivity.

Synthesis and biological evaluation of 2-alkoxycarbonylallyl esters as potential anticancer agents

The reaction of carboxylic acids with Baylis-Hillman reaction derived α-bromomethyl acrylic esters readily provide 2-(alkoxycarbonyl)allyl esters in good to excellent yields. These functionalized allyl esters have been evaluated for their cell proliferation inhibition properties against breast cancer (MDA-MB-231 and 4T1) and pancreatic cancer (MIAPaCa-2) cell lines to explore their potential as anticancer agents. Several of the synthesized derivatives exhibit good potency against all three cancer cell lines. Our structure activity relationship (SAR) studies on 2-carboxycarbonyl allyl esters indicate that substituted aromatic carboxylic acids provide enhanced activity compared to substituted aliphatic carboxylic acid analogs. Di- and tri-allyl esters derived from di-and tri-carboxylic acids exhibit higher inhibition of cell proliferation than mono esters. Further SAR studies indicate that the double bond in the 2-(alkoxycarbonyl)allyl ester is required for its activity, and there is no increase in activity with increased chain length of the alkoxy group. Two lead candidate compounds have been identified from the cell proliferation inhibition studies and their preliminary mechanism of action as DNA damaging agents has been evaluated using epifluorescence and western blot analysis. One of the lead compounds has been further evaluated for its systemic toxicity in healthy CD-1 mice followed by anticancer efficacy in a triple negative breast cancer MDA-MB-231 xenograft model in NOD-SCID mice. These two in vivo studies indicate that the lead compound is well tolerated in healthy CD-1 mice and exhibits good tumor growth inhibition compared to breast cancer drug doxorubicin.

Structure-reactivity relationships of alkyl α-hydroxymethacrylate derivatives

A series of alkyl α-hydroxymethacrylate derivatives with various secondary functionalities (ether, ester, carbonate, and carbamate) and terminal groups (alkyl, cyano, oxetane, cyclic carbonate, phenyl and morpholine) were synthesized to investigate the ef

Enantioselective synthesis of (S)-4-methyleneglutamic acid via tandem conjugate addition-elimination under phase-transfer catalytic conditions

An efficient enantioselective synthetic method for (S)-4-methyleneglutamic acid is reported. Phase-transfer catalytic conjugate addition-elimination of the benzophenone imine of glycine tert-butyl ester in the presence of chiral Cinchona-derived catalysts