13051-21-3

Usage

Uses

Used in Organic Chemistry:
2,2-Dimethyl-Malonic Acid Monomethyl Ester is used as a reagent in various chemical reactions and syntheses, playing a crucial role in the field of organic chemistry. Its unique structure allows it to participate in a wide range of chemical transformations, making it a valuable compound for researchers and chemists.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,2-Dimethyl-Malonic Acid Monomethyl Ester is used as an intermediate in the synthesis of various pharmaceutical compounds. Its versatility in chemical reactions enables the creation of new drug molecules with potential therapeutic applications.
Used in Chemical Research:
2,2-Dimethyl-Malonic Acid Monomethyl Ester is also used as a research tool in chemical research, where it helps scientists understand the properties and reactivity of malonic acid derivatives. This knowledge can be applied to develop new synthetic methods and explore the potential applications of these compounds in various fields.

InChI:InChI=1/C6H10O4/c1-6(2,4(7)8)5(9)10-3/h1-3H3,(H,7,8)

Upstream product

• 6065-54-9 dimethyl dimethylmalonate 
• 141-52-6 sodium ethanolate 
• 67-56-1 methanol 
• 595-46-0 2,2-dimethylmalonic acid 
• 34867-85-1 4,4-dimethyl-1,2-dioxolane-3,5 -dione 
• 15568-97-5 2,2,5,5-tetramethyl-[1,3]dioxane-4,6-dione 
• 934733-52-5 methyl 2-dimethylbismuthanyl-2-methylpropanoate 
• 124-38-9 carbon dioxide 
• 38923-57-8 methyl 2,2-dimethyl-3-oxobutanoate 

Downstream Products

• 64507-20-6 2-chlorocarbonyl-2-methylpropionic acid methyl ester 
• 116070-49-6 dimethyl malonamic acid 
• 547-63-7 Methyl isobutyrate 
• 124-38-9 carbon dioxide 
• 939777-43-2 (S)-3-(2-hydroxy-1-phenylethylamino)-2,2-dimethyl-3-oxopropanoic acid 
• 194031-19-1 N-Allyl-2,2-dimethyl-N-phenyl-malonamic acid methyl ester 
• 194031-18-0 N-But-3-enyl-2,2-dimethyl-N-phenyl-malonamic acid methyl ester 
• 194031-17-9 (E)-3-[2-(2-Methoxycarbonyl-2-methyl-propionylamino)-phenyl]-acrylic acid ethyl ester 
• 194031-13-5 2,2-Dimethyl-malonic acid 2-((E)-2-ethoxycarbonyl-vinyl)-phenyl ester methyl ester 
• 194031-21-5 (E)-4-[(2-Methoxycarbonyl-2-methyl-propionyl)-phenyl-amino]-but-2-enoic acid ethyl ester 
• 194031-14-6 2,2-Dimethyl-malonic acid 2-((E)-2-ethoxycarbonyl-vinyl)-5-methyl-phenyl ester methyl ester 
• 194031-20-4 (E)-5-[(2-Methoxycarbonyl-2-methyl-propionyl)-phenyl-amino]-pent-2-enoic acid ethyl ester 
• 194031-15-7 2,2-Dimethyl-malonic acid 2-((E)-2-ethoxycarbonyl-vinyl)-5-methoxy-phenyl ester methyl ester 
• 1188911-72-9 methyl 3,3,3-trifluoro-2,2-dimethylpropanoate 

Relevant academic research and scientific papers

Glycosylation enhances the anti-migratory activities of isomalyngamide A analogs

Three, new, fully synthetic glycosylated isomalyngamide A analogs 4-6 were prepared and evaluated for their anti-migratory activities in human breast cancer cells. The results of the study show that two glycosylated derivatives 4 and 5, containing mannose and galactose appendages, suppress metastatic events (e.g., migration, invasion and adhesion) in human breast adenocarcinoma MDA-MB-231 cells at "nontoxic" concentration levels. In contrast, derivative 6 that contains a lactose moiety, displays a less potent activity. The findings show that monosaccharide rather than disaccharide appendages to the isomalyngamide A backbone more greatly influence cell migration and invasive ability. Evidence has been gained for a mechanism for inhibition of metastatic activities in MDA-MB-231 cells by 4 and 5, involving inactivation of the expression of p-FAK and paxillin through the integrin-mediated antimetastatic pathway.

Discovery of Peptidomimetic Antibody-Drug Conjugate Linkers with Enhanced Protease Specificity

Antibody-drug conjugates (ADCs) have become an important therapeutic modality for oncology, with three approved by the FDA and over 60 others in clinical trials. Despite the progress, improvements in ADC therapeutic index are desired. Peptide-based ADC linkers that are cleaved by lysosomal proteases have shown sufficient stability in serum and effective payload-release in targeted cells. If the linker can be preferentially hydrolyzed by tumor-specific proteases, safety margin may improve. However, the use of peptide-based linkers limits our ability to modulate protease specificity. Here we report the structure-guided discovery of novel, nonpeptidic ADC linkers. We show that a cyclobutane-1,1-dicarboxamide-containing linker is hydrolyzed predominantly by cathepsin B while the valine-citrulline dipeptide linker is not. ADCs bearing the nonpeptidic linker are as efficacious and stable in vivo as those with the dipeptide linker. Our results strongly support the application of the peptidomimetic linker and present new opportunities for improving the selectivity of ADCs.

Spontaneous reaction of malonyl peroxides with methanol

The spontaneous reaction of disubstituted malonyl peroxides (MPOs) with methanol affording monopermalonic acid monomethyl esters is fast (minutes) for lower homologues but is sharply decelerated (days) for the higher ones. Spirocyclopropyl-MPO is an excep

Generation of carbanions through stibine-metal and bismuthine-metal exchange reactions and its applications to precision synthesis of ω-end-functionalized polymers

Generation of carbanions from organostibines and organobismuthines through heteroatom-metal exchange reactions was examined from synthetic and mechanistic viewpoints. The exchange reaction proceeded spontaneously upon treatment with various organometallic reagents, such as alkyl lithiums, tetraalkyl zincates, and alkyl magnesium halides to afford the corresponding carbanions quantitatively. Due to the high reactivity of these heteroatom compounds, the exchange reactions took place exclusively even in the presence of various polar functional groups, which potentially react with organometallic species. The advantage of this method was exemplified by the end-group transformation of living polymers that bear these heteroatom species at the ω-polymer end, prepared by using organostibine and bismuthine-mediated living radical polymerizations. Various polymers that bear polar functional groups and acidic hydrogen-for example, poly(methyl methacrylate), poly(butyl acrylate), poly(N-isopropyl acrylamide), and poly(2-hydroxyethyl methacrylate)-could be used in the exchange reactions, and subsequent trapping with electrophiles afforded the corresponding polymers with controlled molecular weights, molecular weight distributions, and end-group functionalities. Competition experiments showed that organostibines and organobismuthines were among the most reactive heteroatom compounds towards organometallic reagents and that their high reactivity was responsible for the high chemoselectivity in the exchange reaction. All's well that ends well: The generation of carbanions from organostibine and -bismuthine compounds was achieved thorough a heteroatom-metal exchange reaction (see scheme). The highly chemoselective exchange reaction could be applied to precision synthesis of varieties of ω-end- functionalized polymers that possess a polar functional group.

Selective monoesterification of malonic acid catalyzed by boric acid

Boric acid catalyzes the monoesterification of malonic acid, likely through a chelation mechanism that is not available to the monoester product. Under more forcing conditions, diesters form to some extent, but conditions can be optimized to favour the monoester product (56?80%). With the easily handled solid acid catalyst, these reactions can be run with excess alcohol as solvent or with stoichiometric amounts of alcohol in acetonitrile with moderate heating. CSIRO 2007.