24923-76-0Relevant academic research and scientific papers
Synthesis of methylene butyrolactone polymers from itaconic acid
Trotta, Jacob T.,Jin, Mengyuan,Stawiasz, Katherine J.,Michaudel, Quentin,Chen, Wei-Liang,Fors, Brett P.
, p. 2730 - 2737 (2017)
Herein, we report the transformation of β-monomethyl itaconate, an inexpensive and biorenewable alternative to petroleum feedstocks, to the high-value monomer α-methylene-γ,γ-dimethyl-γ-butyrolactone (Me2MBL) through a selective addition strategy. This strategy is also applied to the synthesis of α-methylene-γ-butyrolactone (MBL, tulipalin A), a monomer that can be polymerized to give materials with desirable properties (high decomposition temperature, glass transition temperature, and refractive index). Subsequent polymerization of both Me2MBL and MBL through reversible addition-fragmentation chain-transfer polymerization generates well-defined poly(Me2MBL) and poly(MBL) (PMBL). Physical characterization of poly(Me2MBL) shows good physical properties comparable with known PMBL materials.
Diastereoselective Alkene Hydroesterification Enabling the Synthesis of Chiral Fused Bicyclic Lactones
Shi, Zhanglin,Shen, Chaoren,Dong, Kaiwu
supporting information, p. 18039 - 18042 (2021/11/16)
Palladium-catalysed diastereoselective hydroesterification of alkenes assisted by the coordinative hydroxyl group in the substrate afforded a variety of chiral γ-butyrolactones bearing two stereocenters. Employing the carbonylation-lactonization products as the key intermediates, the route from the alkenes with single chiral center to chiral THF-fused bicyclic γ-lactones containing three stereocenters was developed.
Enantioselective Construction of Quaternary All-Carbon Centers via Copper-Catalyzed Arylation of Tertiary Carbon-Centered Radicals
Wu, Lianqian,Wang, Fei,Chen, Pinhong,Liu, Guosheng
supporting information, p. 1887 - 1892 (2019/02/05)
An enantioselective copper-catalyzed arylation of tertiary carbon-centered radicals, leading to quaternary all-carbon stereocenters, has been developed herein. The tertiary carbon-centered radicals, including both benzylic and nonbenzylic radicals, were produced by the addition of trifluoromethyl radical to α-substituted acrylamides, and subsequently captured by chiral aryl copper(II) species to give C-Ar bonds with excellent enantioselectivity. Importantly, an acylamidyl (CONHAr) group adjacent to the tertiary carbon radical is essential for the asymmetric radical coupling. The reaction itself features broad substrate scope, excellent functional group compatibility and mild conditions.
Spireasalicin, a New Acylated Quercetin Glycoside from Spiraea salicifolia
Olennikov,Kashchenko
, p. 1038 - 1044 (2017/12/04)
A new acylated quercetin glycoside and 36 known compounds were isolated from flowering runners of Spiraea salicifolia L. (Rosaceae). The structures of the new glycoside quercetin-3-O-[6″-(4?-hydroxy-2?-methylenebutyroyl)]-β-D-glucopyranoside (spireasalicin, 1) and the 36 known compounds were elucidated using UV, IR, and NMR spectroscopy and mass spectrometry. The biological screening of the isolated compounds showed that 1 inhibited α-glucosidase. The contents of several phenolic compounds in S. salicifolia organs were studied and found to be unevenly distributed in the separate plant parts.
Structure-activity relationships of tulipalines, tuliposides, and related compounds as inhibitors of MurA
Mendgen, Thomas,Scholz, Therese,Klein, Christian D.
supporting information; experimental part, p. 5757 - 5762 (2010/12/24)
The enzyme MurA performs an essential step in peptidoglycan biosynthesis and is therefore a target for the discovery of novel antibacterial compounds. We report here the inhibition of MurA by natural products from tulips (tulipalines and tuliposides), and the structure-activity relationships of various derivatives. The inhibition of MurA can be related to antibacterial activity, and MurA is probably one of the relevant molecular targets of the tulipaline derivatives. MurA inhibition by this class of compounds depends on the presence of the substrate UNAG, which indicates non-covalent suicide inhibition as observed previously for cnicin. With respect to selectivity, however, the reactivity against arbitrary sulfhydryl groups, such as in glutathione, could not yet be sufficiently separated from MurA inhibition in the present dataset.
Self-crosslinking hydroxy/alkoxy acyl imidazolidinone monomers
-
, (2008/06/13)
Acyl imidazolidinones and compositions containing the same are disclosed, which are particularly suitable for use as self-crosslinkers and can also be used as wet adhesion properties, especially in latex-based polymer systems. Processes for preparing such compounds, compositions containing the same, as well as additional uses thereof are also disclosed.
Indium-promoted preparation of substituted α-methylene-γ-lactones from 2-(bromomethyl)acrylic acid and carbonyl compounds
Choudhury, Prabir K.,Foubelo, Francisco,Yus, Miguel
, p. 3581 - 3584 (2007/10/03)
The reaction of 2-(bromomethyl)acrylic acid (1) with different carbonyl compounds (2) [CH20, (E)-CH3CH=CHCHO, Pr(i)CHO, Bu(t)CHO, PhCHO, CH3(CH2)5CHO, c-C6H11CHO, Ph2CHCHO, (CH2)5CO] and indium powder in a 1:1 THF:H20 mixture at room temperature affords, after acidic work-up with hydrochloric acid, the corresponding α-methylene-γ-butyrolactones 3.
Electrochemical carboxylation of terminal alkynes catalyzed by nickel complexes: unusual regioselectivity
Dunach, Elisabet,Perichon, Jacques
, p. 239 - 246 (2007/10/02)
The electrochemical reduction of the nickel(II) complex Ni(bipy)3(BF4)2 yields an active catalyst for the regioselective functionalization of the 2-position of terminal alkynes with carbon dioxide.A series of α-substituted acrylic acids have been obtained with selectivities of 65-90percent and fair overall yields.
