25722-14-9Relevant articles and documents
Organocatalytic Trans Semireduction of Primary and Secondary Propiolamides: Substrate Scope and Mechanistic Studies
Grams, R. Justin,Lawal, Monsurat M.,Szwetkowski, Connor,Foster, Daniel,Rosenblum, Carol Ann,Slebodnick, Carla,Welborn, Valerie Vaissier,Santos, Webster L.
supporting information, p. 172 - 178 (2021/10/14)
We report a chemoselective, phosphine-catalyzed semireduction of primary and secondary propiolamides. In the presence of stoichiometric pinacolborane and catalytic n-tributylphosphine, a variety of propiolamides were successfully converted to the corresponding acrylamides in excellent yield with (E)-stereoselectivity. The reaction condition is tolerant of various functional groups including alkene, alkyne, ketone, or ester. Deuterium labeling studies established that the hydride from activated pinacolborane is added to the α-carbon and the proton on the amide nitrogen is abstracted by the ?-carbon to furnish the (E)-acrylamides. DFT calculations revealed a clear energetic driving force for the (E)- over the (Z)-isomer. (Figure presented.).
Learning from Peptides to Access Functional Precision Polymer Sequences
Maron, Eva,Swisher, Jordan H.,Haven, Joris J.,Meyer, Tara Y.,Junkers, Tanja,B?rner, Hans G.
supporting information, p. 10747 - 10751 (2019/07/09)
Functional precision polymers based on monodisperse oligo(N-substituted acrylamide)s and oligo(2-substituted-α-hydroxy acid)s have been synthesized. The discrete sequences originate from a direct translation of side-chain functionality sequences of a peptide with well-studied properties. The peptide was previously selected to solubilize the photosensitizer meta-tetra(hydroxyphenyl)chlorin. The resulting peptidomimetic formulation additives preserve the drug solubilization and release characteristics of the parent peptide. In some cases, superior properties are obtained, reaching up to 40 % higher payloads and 27-times faster initial drug release.
METHOD FOR PRODUCING N-SUBSTITUTED (METH)ACRYLAMIDE
-
Paragraph 0057; 0060, (2017/01/05)
PROBLEM TO BE SOLVED: To provide an industrial method for producing a high-purity alkoxy propionic acid amide derivative and N-substituted (meth)acrylamide in a high yield, which uses a (meth)acrylic acid as a starting material. SOLUTION: There is provided a method for producing an objective compound, N-substituted (meth)acrylamide by the step of: amidating an alkoxy propionic acid derivative, which is synthesized from a (meth)acrylic acid and alcohol and represented by the formula [1], with an amine compound; R3-NH-R4(R3 and R4 each independently represents a hydrogen atom or a linear or branched alkyl group having 1 to 6 carbon atoms or may form a saturated 5- to 7-membered ring with a nitrogen atom supporting them) in the presence of an inorganic material composed mainly of silica as a catalyst to obtain an alkoxy propionic acid amide derivative; and eliminating alcohol by the liquid phase thermal decomposition reaction of the alkoxy propionic acid amide derivative. (R1 represents H or a methyl group; and R2 represents a linear or branched alkyl group having 1 to 6 carbon atoms or an alkenyl group.) COPYRIGHT: (C)2015,JPOandINPIT