2051-76-5Relevant articles and documents
Polymerization of free secondary amine bearing monomers by RAFT polymerization and other controlled radical techniques
Janoschka, Tobias,Teichler, Anke,Krieg, Andreas,Hager, Martin D.,Schubert, Ulrich S.
, p. 1394 - 1407 (2012)
This work describes the polymerization of the free secondary amine bearing monomer 2,2,6,6-tetramethylpiperidin-4-yl methacrylate (TMPMA) by means of different controlled radical polymerization techniques (ATRP, RAFT, NMP). In particular, reversible addition-fragmentation chain transfer (RAFT) polymerization enabled a good control at high conversions and a polydispersity index below 1.3, thereby enabling the preparation of well-defined polymers. Remarkably, the polymerization of the secondary amine bearing methacrylate monomer was not hindered by the presence of the free amine that commonly induces degradation of the RAFT reagent. Subsequent oxidation of the polymer yielded the polyradical poly(2,2,6,6-tetramethylpiperidinyloxy-4-yl methacrylate), which represents a valuable material used in catalysis as well as for modern batteries. The obtained polymers having a molar mass (Mn) of 10,000-20,000 g/mol were used to fabricate well-defined, radical-bearing polymer films by inkjet- printing.
Brotherton et al.
, p. 1283 (1961)
An efficient synthesis of chiral isoquinuclidines by Diels - Alder reaction using Lewis acid catalyst
Hirama, Masafumi,Kato, Yuji,Seki, Chigusa,Nakano, Hiroto,Takeshita, Mitsuhiro,Oshikiri, Noriko,Iyoda, Masahiko,Matsuyama, Haruo
, p. 7618 - 7624 (2010)
The Diels-Alder reaction of 1,2-dihydropyridine derivatives (1-phenoxycarbonyl-1,2-dihydropyridine 1 or 1-methoxycarbonyl-1,2- dihydropyridine 4) with N-acryloyl (1S)-2,10-camphorsultam (1S)-2 {or N-acryloyl (1R)-2,10-camphorsultam (1R)-2} in the presence of Lewis acid, such as titanium tetrachloride, zirconium tetrachloride, and hafnium tetrachloride afforded the endo-cycloaddition product, 2-azabicyclo[2.2.2]octane derivatives in good yields with excellent diastereoselectivity. The absolute stereochemistry assignment of the endo-cycloaddition product (1S)-5a starting from N-acryloyl (1S)-2,10-camphorsultam (1S)-2 has been established to be (1S,4R,7S) and the reaction mechanism was proposed.
Multicatalytic Transformation of (Meth)acrylic Acids: a One-Pot Approach to Biobased Poly(meth)acrylates
Fouilloux, Hugo,Placet, Vincent,Qiang, Wei,Robert, Carine,Thomas, Christophe M.
supporting information, p. 19374 - 19382 (2021/07/21)
Shifting from petrochemical feedstocks to renewable resources can address some of the environmental issues associated with petrochemical extraction and make plastics production sustainable. Therefore, there is a growing interest in selective methods for transforming abundant renewable feedstocks into monomers suitable for polymer production. Reported herein are one-pot catalytic systems, that are active, productive, and selective under mild conditions for the synthesis of copolymers from renewable materials. Each system allows for anhydride formation, alcohol acylation and/or acid esterification, as well as polymerization of the formed (meth)acrylates, providing direct access to a new library of unique poly(meth)acrylates.
Synthesis and structural characterization of a monocarboxylic inhibitor for GRB2 SH2 domain
Haura, Eric B.,Ji, Haitao,Li, Zilu,Schonbrunn, Ernst,Sun, Luxin,Xiao, Tao,Zhang, Min
supporting information, (2021/09/14)
A monocarboxylic inhibitor was designed and synthesized to disrupt the protein–protein interaction (PPI) between GRB2 and phosphotyrosine-containing proteins. Biochemical characterizations show compound 7 binds with the Src homology 2 (SH2) domain of GRB2 and is more potent than EGFR1068 phosphopeptide 14-mer. X-ray crystallographic studies demonstrate compound 7 occupies the GRB2 binding site for phosphotyrosine-containing sequences and reveal key structural features for GRB2–inhibitor binding. This compound with a –1 formal charge offers a new direction for structural optimization to generate cell-permeable inhibitors for this key protein target of the aberrant Ras-MAPK signaling cascade.
