10517-44-9Relevant academic research and scientific papers
Curtius rearrangement of ω-azido acid chlorides: Access to the corresponding ω-azido substituted amines and carbamates, useful building blocks for polyamine syntheses
Khoukhi, Mostafa,Vaultier, Michel,Benalil, Aziza,Carboni, Bertrand
, p. 483 - 487 (1996)
Treatment of ω-azido acid chlorides with trimethylsilyl azide affords ω-azido isocyanates which can be easily converted in good yields to the corresponding ω-azidoamines or ω-azidocarbamates. 1,3- and 1,4-diamine dihydrochlorides can then be prepared by catalytic hydrogenation or reductive alkylation with an organodichloroborane.
A Modular Phosphorylated Glycoluril-Derived Molecular Tweezer for Potent Binding of Aliphatic Diamines
Heilmann, Michael,Tiefenbacher, Konrad
, p. 12900 - 12904 (2019)
A molecular tweezer based on a glycoluril-derived framework bearing four phosphate groups was synthesized and shown to be capable of binding organic amines in aqueous solution. This work reports the Ka values for 30 complexes of this molecular tweezer and amine guests, determined by means of 1H NMR titrations. Both the hydrophobic cavity and the phosphate groups contribute to the binding. Bulkier molecules and molecules bearing negatively charged groups like carboxylates in amino acids bind less tightly due to a steric clash and coulombic repulsion. The narrow cavity and the strong ionic interactions of the phosphate groups with ammonium guests favor binding of aliphatic diamines. These binding properties clearly distinguish this system from structurally related molecular clips and tweezers.
