121065-74-5

Upstream product

• 50-00-0 formaldehyd 
• 27784-76-5 tert-butyl diethylphosphonoacetate 
• 1663-39-4 tert-Butyl acrylate 

Downstream Products

• 1313499-29-4 C₁₅H₁₉NO₄ 
• 141342-95-2 tert-butyl 2-((benzenesulfonyl)methyl)acrylate 
• 53913-96-5 tert-butyl 2-(bromomethyl)acrylate 

Relevant academic research and scientific papers

Convenient synthesis of thermo-responsive PtBA-g-PPEGMEMA well-defined amphiphilic graft copolymer without polymeric functional group transformation

A series of well-defined amphiphilic graft copolymers bearing hydrophobic poly(tert-butyl acrylate) backbone and hydrophilic poly[poly(ethylene glycol) methyl ether methacrylate)] (PPEGMEMA) side chains were synthesized by sequential reversible addition fragmentation chain transfer (RAFT) polymerization and single-electron-transfer living radical polymerization (SET-LRP) without any polymeric functional group transformation. A new Br-containing acrylate monomer, tert-butyl 2-((2-bromoisobutanoyloxy)methyl) acrylate (tBBIBMA), was first prepared, which can be homopolymerized by RAFT to give a well-defined PtBBIBMA homopolymer with a narrow molecular weight distribution (Mw/Mn = 1.15). This homopolymer with pendant Br initiation group in every repeating unit initiated SET-LRP of PEGMEMA at 45 °C using CuBr/dHbpy as catalytic system to afford well-defined PtBBIBMA-g-PPEGMEMA graft copolymers via the grafting-from strategy. The self-assembly behavior of the obtained graft copolymers in aqueous media was investigated by fluorescence spectroscopy and TEM. These copolymers were found to be stimuli-responsive to both temperature and ions. Finally, poly(acrylic acid)-g-PPEGMEMA double hydrophilic graft copolymers were obtained by selective acidic hydrolysis of hydrophobic PtBA backbone while PPEGMEMA side chains kept inert.

PAA-g-PPO amphiphilic graft copolymer: Synthesis and diverse micellar morphologies

A series of well-defined amphiphilic graft copolymers consisting of hydrophilic poly(acrylic acid) backbone and hydrophobic poly(propylene oxide) side chains were synthesized by sequential reversible addition-fragmentation chain transfer (RAFT) polymerization and atom transfer nitroxide radical coupling (ATNRC) chemistry followed by selective hydrolysis of poly(tert-buty1 acrylate) backbone. A new Br- containing acrylate monomer, tert-butyl 2-((2-bromopropanoyloxy)methyl) acrylate, was first prepared, and it can be polymerized via RAFT in a controlled way to obtain a well-defined homopolymer with narrow molecular weight distribution {MwMn = 1.06). Grafting-onto strategy was employed to synthesize PiBA-gPPO well-defined graft copolymers with narrow molecular weight distributions {MwM n = 1.05-1.23) via ATNRC reaction between Br-containing PiBA-based backbone and poly(propylene oxide) with 2, 2, 6, 6-tetramethylpiperidine-l-oxyl (TEMPO) end group using CuBr/PMDETA or Cu/PMDETA as catalytic system. The final PAA-g-PPO amphiphilic graft copolymers were obtained by the selective acidic hydrolysis of PrBA backbone in acidic environment without affecting the side chains. The critical micelle concentrations in aqueous media were determined by a fluorescence probe technique. Diverse micellar morphologies were formed with varying the content of hydrophobic PPO segment.

ATNRC and SET-NRC synthesis of PtBA-g-PEO well-defined amphiphilic graft copolymers

A series of new well-defined amphiphilic graft copolymers containing hydrophobic poly(tert-butyl acrylate) backbone and hydrophilic poly(ethylene oxide) side chains were reported. Reversible addition-fragmentation chain transfer homopolymerization of tert-butyl 2-((2-bromopropanoyloxy)methyl) acrylate was first performed to afford a well-defined backbone with a narrow molecular weight distribution (Mw/Mn = 1.07). The target poly(tert-butyl acrylate)-g-poly(ethylene oxide) (PtBA-g-PEO) graft copolymers with low polydispersities (Mw/Mn = 1.18-1.26) were then synthesized by atom transfer nitroxide radical coupling or single electron transfer-nitroxide radical coupling reaction using CuBr(Cu)/PMDETA as catalytic system. Fluorescence probe technique was employed to determine the critical micelle concentrations (cmc) of the obtained amphiphilic graft copolymers in aqueous media. Furthermore, PAA-g-PEO graft copolymers were obtained by selective acidic hydrolysis of hydrophobic PtBA backbone while PEO side chains kept inert.

Synthesis of PAA-g-PNIPAM well-defined graft polymer by sequential RAFT and SET-LRP and its application in preparing size-controlled super-paramagnetic Fe3O4 nanoparticles as a stabilizer

A series of well-defined double hydrophilic graft copolymers, poly(acrylic acid)-g-poly(N-isopropylacrylamide) (PAA-g-PNIPAM), was employed as a novel water-soluble coating for constructing superparamagnetic iron oxide nanoparticles. The copolymer was synthesized via a three-step procedure: firstly, a well-defined hydrophobic PtBA-based backbone, poly(tert-butyl 2-((2-chloropropanoyloxy)-methyl)acrylate)-co-poly(tert-butyl acrylate), (PtBCPMA19-co-PtBA18), was prepared through RAFT copolymerization of a new trifunctional acrylic monomer, tert-butyl 2-((2-chloropropanoyloxy)methyl)acrylate and tert-butyl acrylate; secondly, taking this backbone as a macroinitiator to initiate SET-LRP of N-isopropylacrylamide resulted in well-defined (poly(tert-butyl 2-((2-chloropropanoyloxy)methyl)-acrylate)-co-poly(tert-butyl acrylate))-g-poly(N-isopropylacrylamide) ((PtBCPMA-co-PtBA)-g-PNIPAM) amphiphilic graft copolymers with relatively narrow polydispersities (M w/Mn ≤ 1.31); thirdly, handling (PtBCPMA-co-PtBA)-g- PNIPAM in acidic conditions afforded PAA-g-PNIPAM graft copolymers. The resulting PAA-g-PNIPAM copolymers were directly utilized as a polymeric stabilizer in the preparation of superparamagnetic Fe3O4 nanoparticles. The particle size can be readily tuned in the range of 12.1-23.2 nm by varying the amount of PAA-g-PNIPAM copolymer or the length of PNIPAM side chain. Besides, the structure and properties of prepared Fe3O 4/polymer nanocomposites were characterized by XRD, FT-IR, TGA, TEM, and magnetic measurement in detail.

Convenient synthesis of PtBA-g-PMA well-defined graft copolymer with tunable grafting density

A series of well-defined graft copolymers, consisting of poly(tert-butyl acrylate) backbone and poly (methyl acrylate) side chains, were synthesized by the combination of reversible addition-fragmentation chain transfer (RAFT) polymerization and atom transfer radical polymerization (ATRP). A new acrylate monomer containing ATRP initiation group, tert-butyl 2-((2-bromopropanoyloxy) methyl)acrylate, was first prepared, which can be homopolymerized or copolymerized with tert-butyl acrylate by RAFT in a controlled way to obtain well-defined homopolymers and copolymers with narrow molecular weight distributions (Mw/Mn w/Mn 1.28) with controllable grafting densities via the grafting-from strategy without any polymeric functional group transformation. Finally, the poly(tert-butyl acrylate) backbone was selectively hydrolyzed in acidic environment without affecting the poly(methyl acrylate) side chains to give poly(acrylic acid)-g-poly(methyl acrylate) amphiphilic graft copolymers

Bicyclo[3.2.0]heptane as a Core Structure for Conformational Locking of 1,3-Bis-Pharmacophores, Exemplified by GABA

The synthesis and X-ray crystal structures of syn and anti 4-N-Boc-aminobicyclo[3.2.0]heptane-1-carboxylic acids are described. The placement of the N-Boc-amino groups in the two stereoisomers in either pseudo-equatorial or pseudo-axial positions renders the molecules conformationally locked, with N-Boc-protected γ-aminobutyric acid (GABA) embedded within the bicyclic core. Despite the different conformations of the urethane and distinct crystal packing, the bicyclic core units of the two stereoisomers adopt virtually identical structures. They correspond to in silico models of the parent bicyclic core and a systematic array of disubstituted derivatives. The study documents an intrinsic property of the bicyclo[3.2.0]heptane core to favor adoption of a boat-like conformation, which is largely unaffected by various substitution patterns. The structural concepts are useful in the design of molecules with spatial and directional fixation of pharmacophoric groups.

Synthesis of starlike PtBA-g-PEO amphiphilic graft copolymer via highly efficient Cu-catalyzed SET-NRC reaction at ambient temperature

Two new amphiphilic star graft copolymers bearing hydrophobic poly(tert-butyl acrylate) backbone and hydrophilic poly(ethylene oxide) (PEO) side chains with different molecular weights were synthesized by sequential reversible addition fragmentation chain

Synthesis of PAA-g-PNVCL Graft Copolymer and Studies on Its Loading of Ornidazole

A well-defined amphiphilic graft copolymer, consisting of hydrophobic poly(tert-butyl acrylate) (PtBA) backbone and hydrophilic poly(N-vinylcaprolactam) (PNVCL) side chains, was synthesized by successive reversible addition-fragmentation chain transfer (RAFT) polymerization and atom transfer radical polymerization (ATRP). A new acrylate monomer bearing a chlorine-based initiating group, tert-butyl 2-((2-chloropropanoyloxy)methyl)acrylate, was first RAFT homopolymerized in a controlled way to give a well-defined homopolymer with a narrow molecular weight distribution (Mw/Mn=1.15). This homopolymer directly initiated ATRP of N-vinylcaprolactam (NVCL) to afford a well-defined PtBA-g-PNVCL graft copolymer (Mw/Mn=1.22) via the grafting-from strategy without polymeric functionality transformation. PAA-g-PNVCL graft copolymer was prepared by selectively hydrolyzing PtBA-g-PNVCL. Ornidazole (ONZ)-loaded polymeric micelles using PAA-g-PNVCL copolymer as carrier were prepared by physical entrapping. Drug release experiment of the nano-carrier indicated the pH-dependent drug release characteristics.

Metal-free access to 3-allyl-2-alkoxychromanonesviaphosphine-catalyzed alkoxy allylation of chromones with MBH carbonates and alcohols

A metal-free access to 3-allyl-2-alkoxychromanones by PPh3-catalyzed alkoxy allylation of chromones with MBH carbonates and alcohols is described. This reaction is performed under mild conditions and it shows good functional group tolerance, providing a series of functionalized chromanones in moderate to high yields with excellent diastereoselectivities. Deuterium-labeling experiments to probe a possible mechanism and scale-up reaction were also conducted.

Copper-catalyzed radical oxyallylation of olefins for the construction of alkene-containing isoxazolines

A radical-mediated approach to alkene oxyallylation using allylic oximes is described. The reaction proceeds under copper-catalytic redox-neutral conditions and tolerates various functional groups. This protocol thus enables the synthesis of structurally valuable isoxazolines and the introduction of a versatile olefin motif in a single step.