Synonyms:dimethyl malonate;methyl malonate
99% *data from raw suppliers
Methylmalonate *data from reagent suppliers
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There total 117 articles about Dimethyl malonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
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2,6-bis-(4-methoxy-phenyl)-4-oxo-cyclohexane-1,1-dicarboxylic acid dimethyl ester
2-(4-methoxy-phenyl)-4-oxo-6-styryl-cyclohexane-1,1-dicarboxylic acid dimethyl ester
3-[4-(3-chloro-4-methyl-phenyl)-piperazino]-3-oxo-propionic acid
3-[4-(3-chloro-4-methyl-phenyl)-piperazino]-3-oxo-propionic acid methyl ester
The study presents an innovative approach to C-C bond formation through NHC-catalyzed Michael addition to α,β-unsaturated aldehydes, utilizing redox activation. The researchers, Suman De Sarkar and Armido Studer, explore the use of N-heterocyclic carbenes (NHCs) to activate α,β-unsaturated aldehydes, which then react with various 1,3-dicarbonyl compounds to form dihydropyranones. They demonstrate that this method is effective with different nucleophiles and enals, achieving high yields and selectivity under mild conditions. The process involves a two-step umpolung reaction at the β-position of the α,β-unsaturated aldehyde, followed by a redox-type activation. The study also includes control experiments to rule out alternative mechanisms, such as kinetic O-acylation, and provides a proposed catalytic cycle for the process. This work contributes to the field of organocatalysis by offering a new strategy for conjugate addition reactions using soft C-nucleophiles and showcases the potential of NHCs in redox activation.
The research focuses on the synthesis, structural characterization, and catalytic application of planar chiral alkenylferrocene phosphanes, specifically (Sp)-[Fe(g5-C5H3-1-PPh2-2-CH@CR2)(g5-C5H5)] derivatives, in asymmetric allylic alkylation reactions. The study involves the preparation of these phosphane ligands through alkenylation of (Sp)-2-(diphenylphosphanyl)ferrocenecarboxaldehyde and their subsequent testing as ligands in palladium-catalyzed allylic alkylation of 1,3-diphenyprop-2-en-1-yl acetate with dimethyl malonate. The experiments utilized various analytical techniques, including NMR, ESI MS, IR spectroscopy, and X-ray diffraction, to characterize the ligands and their complexes. The research also includes the synthesis and structural characterization of a model palladium complex, [Pd(g3-1,3-Ph2C3H3){(Sp)-2-g2:jP}]ClO4 ((Sp)-12), to understand the stereochemical course of the alkylation reaction. The study found that while all phosphanylalkenes formed active catalysts, the enantioselectivity was only poor to moderate, with the specific enantiomeric excess and configuration of the preferred product strongly depending on the ligand structure.
The study presents the synthesis and application of two new chiral ligands, phosphinooxathianes 3 and 6, in palladium-catalyzed asymmetric allylic alkylation reactions. The primary chemicals used were 1,3-diphenyl-2-propenyl acetate (substrate 7), dimethyl malonate (nucleophile), [PdCl(n-C3H5)]2 (palladium catalyst), and the chiral ligands 3 and 6. The purpose of these chemicals was to investigate the enantioselective allylic alkylation reaction, aiming to achieve high enantiomeric excess (a measure of the purity of the chiral product). The study found that ligand 3, in particular, was effective under specific reaction conditions, yielding an allylation product with up to 94% enantiomeric excess. The research aimed to develop efficient enantioselective catalysts for asymmetric reactions, with the potential to improve chemical yields and enantiomeric purity in synthetic organic chemistry.
The research investigates the enzyme-catalyzed hydrolysis of dialkylated propanedioic acid diesters, focusing on how the chain length of the alkyl substituents impacts enantioselectivity. Pig liver esterase and chymotrypsin were utilized as catalysts. A notable reversal of enantioselectivity from pro-5 to pro-1 was observed based on the alkyl chain length. For instance, substrates with short alkyl chains (1-3 and 8-10) yielded up to 73% enantiomeric excess (e.e.) of the R-enantiomer when hydrolyzed by pig liver esterase, while longer chain homologues (4-6 and 11) produced the L-enantiomer with almost 90% e.e. In the case of chymotrypsin, it selectively hydrolyzed benzylmethylpropanedioic acid diesters to yield optically pure monoesters. The study also involved the synthesis of dialkylated propanedioic acid diesters through reactions with sodium, methanol, propanedioic acid dimethyl ester, and various alkyl halides. The enantiomeric excess was determined using NMR spectroscopy in the presence of optically pure l-phenylethylamine. The absolute configuration was established through a series of chemical transformations, including acyl-azide formation and Curtius rearrangement, starting from the optically pure monoester obtained via chymotrypsin hydrolysis. The research provides valuable insights into the structural effects on the kinetics and enantioselectivity of enzyme-catalyzed reactions, which can be applied in the synthesis of chiral compounds with biological or pharmacological significance.
This research investigates the bimodal reactivity of α,β-unsaturated acylzirconocene chloride with various nucleophiles, aiming to explore its potential applications in organic synthesis. The study found that the reactivity at the α- and acyl carbons of the compound depends on the type of nucleophile used. With stable carbon nucleophiles like the sodium salt of dimethyl malonate and malononitrile, Michael addition products were obtained in good yields. However, when reacting with higher-order cyanocuprate reagents, such as R2Cu(CN)Li2, saturated ketones were formed instead, indicating the formation of a ketone α,β-dianion species. The conclusions suggest that the electronic nature of the acylzirconocene chloride can be tuned by the choice of nucleophile, opening up new synthetic possibilities for acylzirconocene complexes.
The study investigates a novel "umpolung" in C-C bond formation catalyzed by triphenylphosphine. The Michael addition reaction, where a nucleophile adds to an α,β-unsaturated carbonyl compound, is a fundamental synthetic reaction in organic chemistry. Typically, the γ-carbon in such compounds acts as a nucleophile due to conjugation with an electron-withdrawing group. However, this study demonstrates that triphenylphosphine can induce the γ-carbon to act as an electrophile, facilitating nucleophilic addition. The researchers used a mixture of methyl 2-butynoate and dimethyl malonate, with triphenylphosphine as a catalyst, acetic acid, and sodium acetate in toluene. They observed the formation of a 1:1 adduct, with yields varying based on the concentration of triphenylphosphine. The study explores the range of pronucleophiles that can participate in this reaction, finding that compounds with pKa < 16 work well, while introducing alkyl groups on the acidic carbon of the pronucleophile reduces yield. The study also examines the effects of different substituents on the acetylenic acceptor, such as esters, amides, and ketones, and proposes a mechanism where triphenylphosphine acts as a nucleophilic trigger, enabling unprecedented regioselectivity and atom economy in the addition process.
The study focuses on the synthesis and chemical behavior of 5-chloro-1,2,4-thiadiazol-2-ium chlorides (salts 3), which are useful precursors to a variety of 6aλ4-thiapentalene systems. These salts were obtained by treating formimidoyl isothiocyanates (1) with an excess of methanesulfenyl chloride. The salts exhibited interesting chemical behavior towards several nitrogen and carbon nucleophiles, leading to the formation of diverse polyheterapentalene systems. Key chemicals used in the study include isothioureas, acetamide, p-toluidine, phenyl isothiocyanate, and active methylene compounds like methyl cyanoacetate and dimethyl malonate. These reagents served to displace the 5-chlorine atom of the salts, leading to the formation of various heterocyclic compounds such as 1H,6H-6aλ4-thia-1,3,4,6-tetraazapentalenes (7), 6H-6aλ4-thia-1-oxa-3,4,6-triazapentalene (9), and other thiapentalene derivatives. The study utilized IR and NMR spectroscopic data for structural assignments and received additional support from X-ray analysis of substrate 16a. The purpose of these chemicals was to explore the reactivity of the thiadiazolium salts and to synthesize new hypervalent sulfur compounds through nucleophilic substitution reactions.
The research aims to develop an efficient and concise method for synthesizing the eudesmane skeleton, which is a significant structural motif in various sesquiterpenes, including (±)-β-eudesmol, cryptomeridiol, and neointermediol. The study employs a strategy based on the use of key intermediates like A or B, which undergo intramolecular cyclization via aldol condensation or Michael reaction. The synthesis starts from readily available 3-vinyl-2-cyclohexen-1-one, which is treated with dimethyl malonate in the presence of sodium methoxide to yield the Michael adduct. Subsequent steps involve acetalization, reduction with lithium aluminum hydride, selective benzylation, oxidation with pyridinium dichromate (PDC), and catalytic hydrogenation. The crucial step is the intramolecular aldol condensation, which constructs the desired α,β-unsaturated ketone. The final steps include oxidation, esterification, and selective reduction to obtain the target compounds. The research concludes that this approach provides a general method for constructing eudesmane sesquiterpenes, offering a formal total synthesis of (±)-β-eudesmol and its related compounds.
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