42937-74-6

Usage

Uses

Used in Pharmaceutical Industry:
DIMETHYL 2-(HYDROXYIMINO)MALONATE is used as a building block for the synthesis of various pharmaceutical compounds for [application reason]. Its malonic acid derivative structure allows for the creation of diverse molecules with potential therapeutic applications.
Used in Chemical Research:
DIMETHYL 2-(HYDROXYIMINO)MALONATE is used as a research compound for studying the properties and reactions of malonic acid derivatives and hydroxyimino compounds. This can lead to a better understanding of their potential applications in various fields.
Used in Material Science:
DIMETHYL 2-(HYDROXYIMINO)MALONATE is used as a component in the development of new materials with unique properties, such as improved stability or reactivity, due to its malonic acid and hydroxyimino structures.

InChI:InChI=1/C5H7NO5/c1-10-4(7)3(6-9)5(8)11-2/h9H,1-2H3

Upstream product

• 65390-51-4 dimethyl 2,2-dihydroxymalonate 
• 624-91-9 methyl nitrite 
• 108-59-8 malonic acid dimethyl ester 
• 67-56-1 methanol 
• 81539-54-0 isonitroso Meldrum’s acid 
• 16642-51-6 N-methoxy-N-amine N-oxide 
• 3298-40-6 mesoxalate de methyle 
• 7803-49-8 hydroxylamine 
• 5437-67-2 dimethyl 2-nitromalonate 

Downstream Products

• 53704-09-9 dimethyl 2-aminomalonate 
• 71721-66-9 hydroxyimino-malonic acid diamide 
• 55590-76-6 dimethyl O-methylisonitrosomalonate 
• 91396-08-6 <2-Chlor-benzoyl>-aminomalonsaeure-dimethylester 
• 91958-60-0 Phenylacetyl-aminomalonsaeure-dimethylester 
• 69740-31-4 Dimethylmesoxalat-O-benzhydryloxim 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 82874-74-6 dimethyl (benzyloxyimino)malonate 
• 103218-12-8 dimethyl <(phenylmethyl)imino>malonate N-oxide 
• 90786-16-6 dimethyl 7-phenyl-2-oxa-3,7-diazabicyclo<3.3.0>octane-4,4-dicarboxylate 
• 158615-32-8 C₁₂H₁₁NO₆ 
• 54972-12-2 dimethyl 2-((tosyloxy)imino)malonate 
• 37447-35-1 2-benzyloxycarbonylaminomalonic acid dimethyl ester 
• 27160-23-2 dimethyl formamidomalonate 

Relevant academic research and scientific papers

Stability of electron deficient activated nitronates under neutral and Lewis acid catalyzed conditions. Facile nitronate cycloaddition reactions to the magnesium alkoxides of allylic alcohols leading to isoxazolidines and isoxazolines

N-Methoxy-N-[bis(methoxycarbonyl)methylene]amine N-oxide and N-methoxy- N-(methoxycarbonylmethylene)amine N-oxide as electron-deficient activated nitronates, show an exceptionally high reactivity to the magnesium alkoxides of allylic alcohols. Isoxazolidines or isoxazolines are formed as cycloadducts, depending upon the substitution pattern of the allylic alcohols. When the latter C-monosubstituted nitronate is treated with a catalytic amount of boron trifluoride etherate, the corresponding nitrile oxide is smoothly generated through β-elimination of methanol.

Dimethylmalonato zinc complexes as molecular precursors for electronic grade zinc oxide: Towards a systematic ligand design by understanding molecular decomposition mechanisms

Zinc complexes with dimethyl 2-hydroxyimino- and 2-nitromalonate (dmm-NOH and Hdmm-NO2, respectively) were synthesized and examined as potential precursors for nanocrystalline zinc oxide. The functionalised 1,3-diketones are sufficiently acidic to allow direct synthesis from hydrozincite or zinc 2-propoxide as well as their full spectroscopic and analytical characterization. Their nominal elemental compositions of [Zn 4O(dmm-NO)6] and [Zn3(OH)4(dmm- NO2)2] suggest the presence of multinuclear cage structures with oxo- or hydroxo-bridging ligands. This assumption is in accordance with the obtained spectroscopic data. Thermogravimetry coupled with mass spectrometry and infrared spectroscopy (TG/MS and TG-IR) indicate the formation of dimethylcarbonate and methanol during the decomposition. Both precursors exhibit good film formation properties and the obtained zinc oxide was further characterized by XRD, SEM, TEM and PL. Finally, the semiconducting electronic behaviour of the obtained nanocrystalline ZnO was studied in a field-effect transistor (FET) device. Copyright

Atropisomerism in monopyrroles

As observed by NMR, iodopyrroles 1a and 1b (ethyl and methyl 3,5-dimethyl-4-[(1′-iodo-2′,2′-dimethyl)propyl]pyrrole-2- carboxylate) and a variety of related derivatives with iodine replaced by methoxy 2, thiomethyl 3, acetic acid esters 4, propionic acid ester 5 or malonic esters 6 exhibit restricted rotation about the C(4)-C(1′) bond due to the bulky tert-butyl group and an ortho effect from the sterically crowded 3,5-dimethylpyrrole. Most of the compounds, which are members of the rare class of atropisomers due to restricted rotation about an sp3-sp2 C-C bond, undergo diastereomeric enrichment by preparative TLC and crystallization. From dynamic NMR studies of the enriched diastereomers one can determine kinetic and thermodynamic parameters associated with the atropisomerism, e.g., ΔG? ～24 kcal/mol for 1 and 5 (313 K), ～22 kcal/mol for 3 (273 K), and ～25 kcal/mol for 6 (313 K) in C2D2Cl4 solvent.

Reaction of diaziridine-3,3-dicarboxylic acid dihydrazide with acetone

Using the reaction of diaziridine-3,3-dicarboxylic acid dihydrazide with acetone, new bicyclic diaziridines 7a,b have been obtained instead of expected tricyclic heterocycle 8.

An enantiomerically pure bilirubin. Absolute configuration of (αR,α′R)-dimethylmesobilirubin-XIIIα

Enantiomerically pure (+)-(αR,α′R)-dimethylmesobilirubin-XIIIα 1 and its (αS,α′S) enantiomer ent-1 were synthesized in ten steps from simple precursors. Resolution was achieved at an early stage in the synthesis, with a racemic monopyrrole precursor rac-6 being converted to its amides 8 with (1S)-camphor-2,10-sultam. Resolution of 8 to 99% d.e. was accomplished in three crystallizations, and the absolute configuration of the acid 6 was deduced by X-ray crystallography of the more crystalline, diastereomerically pure amide 7. Circular dichroism spectroscopy of 1 showed intense bisignate Cotton effects: Δε435max = +344, Δε391max = -193 (CHCl3), as expected for a molecular exciton, and consistent with a P-helical intramolecularly hydrogen-bonded ridge-tile conformation. The Cotton effect magnitudes of 1 match almost exactly those found for (-)-(βS,β′S)-dimethylmesobilirubin-XIIIα 11 and (+)-(αR,β′R)-dimethylmesobilirubin-XIIIα. However, the Cotton effect of the pseudo-meso diastereomer (αR,β′S)-dimethylmesobilirubin-XIIIα 12 is not zero. Its large positive exciton couplet and 1H NMR NOE analysis confirm that an α-CH3 exerts a greater steric demand than a β-CH3 - by a factor of ～3.

ANTIVIRAL 1,3-DI-OXO-INDENE COMPOUNDS

The invention provides compounds of Formula (I): as described herein, along with pharmaceutically acceptable salts, pharmaceutical compositions containing such compounds, and methods to use these compounds, salts and compositions for treating viral infections.

Unified Strategy to Amphenicol Antibiotics: Asymmetric Synthesis of (-)-Chloramphenicol, (-)-Azidamphenicol, and (+)-Thiamphenicol and Its (+)-3-Floride

The asymmetric synthesis of (-)-chloramphenicol, (-)-azidamphenicol, and (+)-thiamphenicol and its (+)-3-floride, (+)-florfenicol, is reported. This approach toward the amphenicol antibiotic family features two key steps: (1) a cinchona alkaloid derived urea-catalyzed aldol reaction allows highly enantioselective access to oxazolidinone gem-diesters and (2) a continuous flow diastereoselective decarboxylation of thermally stable oxazolidinone gem-diesters to form the desired trans-oxazolidinone monoesters with two adjacent stereocenters that provide the desired privileged scaffolds of syn-vicinal amino alcohols in the amphenicol family.

PREPARATION OF SECONDARY AMINES WITH ELECTROPHILIC N-LINCHPIN REAGENTS

In one aspect, the present disclosure provides methods of preparing a secondary amine. In some embodiments, the secondary amine comprises two different groups or two identifical groups. Also provided herein are compositions for use in the preparation of the secondary amine.

Copper-Catalyzed Carbonyl Group Controlled Coupling of Isatin Oximes with Arylboronic Acids To Prepare N-Aryloxindole Nitrones

A variety of (E)-N-aryloxindole nitrones were prepared in good to excellent yields by using a copper-catalyzed coupling reaction of isatin oximes and arylboronic acids under mild conditions. Various arylboronic acids that contain sensitive functional groups were tolerated in the transformation, and detailed studies show that the carbonyl group of the isatin oximes serves as a ligand to control the formation of the (E)-oxindole nitrones. This method to prepare (E)-N-aryloxindole nitrones was easily performed on a gram scale and efficiently used to synthesize estrone-derived oxindole nitrone in high yield.

Practical Singly and Doubly Electrophilic Aminating Agents: A New, More Sustainable Platform for Carbon-Nitrogen Bond Formation

Given the importance of amines in a large number of biologically active natural products, active pharmaceutical ingredients, agrochemicals, and functional materials, the development of efficient C-N bond-forming methods with wide substrate scope continues to be at the frontier of research in synthetic organic chemistry. Here, we present a general and fundamentally new synthetic approach for the direct, transition-metal-free preparation of symmetrical and unsymmetrical diaryl-, arylalkyl-, and dialkylamines that relies on the facile single or double addition of readily available C-nucleophiles to the nitrogen atom of bench-stable electrophilic aminating agents. Practical single and double polarity reversal (i.e., umpolung) of the nitrogen atom is achieved using sterically and electronically tunable ketomalonate-derived imines and oximes. Overall, this novel approach represents an operationally simple, scalable, and environmentally friendly alternative to transition-metal-catalyzed C-N cross-coupling methods that are currently used to access structurally diverse secondary amines.