Zotou, "Determination of glutathione in baker's yeast by capillary electrophoresis using methyl propiolate
as derivatizing reagent," Journal of Chromatography A, vol.
Summary: Ethyl-6-(4-(ethoxycarbonyl)-1H-1,2,3-triazol-1-yl)pyridine-3-carboxylate (1), was synthesized via click reaction between ethyl tetrazolo[1,5-a]pyridine-6-carboxylate and ethyl propiolate in tetrahydrofuran (THF) in the presence of catalytic amount of a copper acetate.
Ethyl propiolate (117.7 mg, 1.2 mmol) was added to a solution of ethyl tetrazolo[1,5-a]pyridine-6-carboxylate (192.20 mg, 1 mmol) and Cu(OAc)2 (3 mg, 0.025 mmol) in THF (2 mL) using liquid N2.
Wang et al., "Selective induction of tumor cell apoptosis by a novel P450-mediated reactive oxygen species (ROS) inducer methyl 3-(4-nitrophenyl) propiolate
," Journal of Biological Chemistry, vol.
Most interestingly, methyl propiolate
and 2,3-dimethyl-2-butene condense in the metals' coordination spheres to form cationic lactone-containing species in the manner depicted in eq 20, ie.
Hu, "Copper(I) acetate-catalyzed cycloaddition between azomethine imines and propiolates under additive-free conditions," European Journal of Organic Chemistry, vol.
Ogino, "Chiral Bis(Imidazolidine)pyridine-Cu complex-catalyzed enantioselective [3+2]-cycloaddition of azomethine imines with propiolates," Molecules, vol.
Kinetic glutathione chemoassay to quantify thiol reactivity of organic electrophiles--Application to alpha,beta-unsaturated ketones, acrylates, and propiolates
. Chem Res Toxicol 22, 742-750.