597-04-6

Usage

Uses

Used in Chemical Synthesis:
2,2-DIMETHYL-3-OXO-BUTYRIC ACID ETHYL ESTER is used as a key intermediate in the synthesis of esters of α,α-dimethyl-β-keto acids for the production of various chemicals and pharmaceuticals. Its unique chemical structure allows for the creation of a wide range of compounds with diverse applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,2-DIMETHYL-3-OXO-BUTYRIC ACID ETHYL ESTER is used as a building block for the development of new drugs. Its ability to form esters of α,α-dimethyl-β-keto acids makes it a valuable component in the synthesis of various medicinal compounds, contributing to the advancement of drug discovery and development.
Used in Flavor and Fragrance Industry:
2,2-DIMETHYL-3-OXO-BUTYRIC ACID ETHYL ESTER, due to its unique chemical properties, is also utilized in the flavor and fragrance industry. It can be used to create a variety of scent profiles and enhance the aroma of various products, such as perfumes, cosmetics, and household items.
Used in the Synthesis of Dyes and Pigments:
2,2-DIMETHYL-3-OXO-BUTYRIC ACID ETHYL ESTER is also employed in the synthesis of dyes and pigments, where its chemical properties allow for the creation of a diverse range of colorants used in various applications, including textiles, plastics, and printing inks.

InChI:InChI=1/C8H14O3/c1-5-11-7(10)8(3,4)6(2)9/h5H2,1-4H3

Upstream product

• 609-14-3 2-acetylpropanoic acid ethyl ester 
• 600-00-0 ethyl 2-bromoisobutyrate 
• 38923-57-8 methyl 2,2-dimethyl-3-oxobutanoate 
• 141-52-6 sodium ethanolate 
• 141-97-9 ethyl acetoacetate 
• 74-88-4 methyl iodide 
• 75-36-5 acetyl chloride 
• 97-62-1 Ethyl isobutyrate 
• 64-17-5 ethanol 
• 30274-05-6 2,2-dimethyl-3-oxobutyryl chloride 
• 108-24-7 acetic anhydride 
• 141-78-6 ethyl acetate 
• 75-09-2 dichloromethane 
• 119-61-9 benzophenone 

Downstream Products

• 26823-10-9 2,2-dimethyl-3,5-dioxo-hexanoic acid ethyl ester 
• 97-62-1 Ethyl isobutyrate 
• 563-80-4 3-methyl-butan-2-one 
• 3201-20-5 2,4-dihydro-4,4,5-trimethyl-3H-pyrazol-3-one 
• 56663-75-3 2,2-dimethyl-3-chloro-3-butenoic acid 
• 66483-64-5 2,2-Dimethyl-3-oxobutanamid 
• 98485-46-2 α,α-dimethylacetoacetic acid 
• 7505-94-4 ethyl 3-hydroxy-2,2-dimethylbutanoate 
• 63891-88-3 ethyl 4-bromo-2,2-dimethyl-3-oxobutanoate 
• 20949-28-4 ethyl 2-(1H-indol-2-yl)-2-methylpropanoate 
• 947-82-0 4,4,5-trimethyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one 
• 31469-16-6 1-ethoxy-1-((trimethylsilyl)oxy)-2-methylpropene 
• 57146-99-3 2,2-Dimethyl-3-hydroxy-3-methyl-4-benzoyl-butansaeureaethylester 
• 57146-98-2 2-<(1-Hydroxy-1-methyl-2,2-dimethyl-2-aethoxycarbonyl)-aethyl>-cyclohexanon-(1) 

Relevant academic research and scientific papers

NMR Spectroscopic Studies of Intermediary Metabolites of Cyclophosphamide. 2. Direct Observation, Characterization, and Reactivity Studies of Iminocyclophosphamide and Related Species

4-Hydroxy-5,5-dimethylcyclophosphamide (6) was synthesized as a stable (to fragmentation) analogue of 4-hydroxycyclophosphamide (1).In anhydrous Me2SO-d6 (0.03 mol percent water), cis- and trans-6 were observed by multinuclear NMR spectroscopy to equlibrate with α,α-dimethylaldophosphamide (7) and 5,5-dimethyliminocyclophosphamide (8).Identification of 8 was based on 1H, 13C, and 31P chemical shifts, selective INEPT and two-dimensional NMR correlation experiments, and temperature-dependent equilibria data.The interconversion of cis-/trans-6 and -7 was also observed in lutidine buffer; 8 was not detected under the aqueous conditions.In Me2SO-d6, hydroxy metabolite 1 underwent dehydration to give iminocyclophosphamide (5), as evidenced by chemical shift data and a selective INEPT experiment.Concentrations of cis-/trans-1, aldophosphamide (2), and 5 were found to be temperature-dependent with higher temperatures favoring 2 and 5 in a reversible manner, thus indicating that 1/2/5 were interconverting.The addition of small amount of water to Me2SO-d6 solutions of imine 5 resulted in the immediate disappearance of its NMR signals.The role of imine 5 in the conversion of 1 to C-4 substituted analogues of 1 was elucidated for the formation of 4-cyanocyclophosphamide (3a) from 1 and sodium cyanate in lutidine buffer.

A Readily Accessible Chiral NNN Pincer Ligand with a Pyrrole Backbone and Its Ni(II) Chemistry: Syntheses, Structural Chemistry, and Bond Activations

A new class of chiral C2-symmetric N-donor pincer ligands, 2,5-bis(2-oxazolinyldimethylmethyl)pyrroles (PdmBox)H, was synthesized starting from the readily available ethyl 2,2-dimethyl-3-oxobutanoate (1). The synthesis of the ligand backbone was achieved by oxidative enole coupling with CuC12 followed by Paal-Knorr-type pyrrole synthesis. The corresponding protioligands (RPdmBox)H (R = iPr: 5a; Ph: 5b) were obtained by condensation with amino alcohols and subsequent zinc-catalyzed cyclization. Reaction of the lithiated ligands with [NiCl2(dme)] yielded the corresponding square-planar nickel(II) complexes [(RPdmBox)NiCl] (6a/b). Salt metathesis of 6a with the corresponding alkali or cesium salts in acetone led to the formation of air- and moisture-stable [(iPrPdmBox)NiX] (X = F (7), X = Br (8), X = I (9), X = N3 (10), X = OAc (11). Furthermore, the conversion of [(iPrPdmBox)NiF] (7) with hydride transfer reagents such as PhSiH3 led to the stable hydrido species [(iPrPdmBox)NiH] (27), the stoichiometric transformations of which were studied. Treatment of 6a with organometallic reagents such as ZnEt2, PhLi, PhCCLi, NsLi, or (4FBn)2Mg(THF)2 gave the corresponding alkyl, alkynyl, or aryl complexes. The availability of the new nonisomerizable PdmBox pincer ligands allowed the comparative study of their ligation to square-planar complexes as helically twisted spectator ligands as opposed to the enforced planar rigidity of their iso-PmBox analogues and the way this influences the reactivity of the Ni complexes.

Five Roads That Converge at the Cyclic Peroxy-Criegee Intermediates: BF3-Catalyzed Synthesis of β-Hydroperoxy-β-peroxylactones

We have discovered synthetic access to β-hydroperoxy-β-peroxylactones via BF3-catalyzed cyclizations of a variety of acyclic precursors, β-ketoesters and their silyl enol ethers, alkyl enol ethers, enol acetates, and cyclic acetals, with H2O2. Strikingly, independent of the choice of starting material, these reactions converge at the same β-hydroperoxy-β-peroxylactone products, i.e., the peroxy analogues of the previously elusive cyclic Criegee intermediate of the Baeyer-Villiger reaction. Computed thermodynamic parameters for the formation of the β-hydroperoxy-β-peroxylactones from silyl enol ethers, enol acetates, and cyclic acetals confirm that the β-peroxylactones indeed correspond to a deep energy minimum that connects a variety of the interconverting oxygen-rich species at this combined potential energy surface. The target β-hydroperoxy-β-peroxylactones were synthesized from β-ketoesters, and their silyl enol ethers, alkyl enol ethers, enol acetates, and cyclic acetals were obtained in 30-96% yields. These reactions proceed under mild conditions and open synthetic access to a broad selection of β-hydroperoxy-β-peroxylactones that are formed selectively even in those cases when alternative oxidation pathways can be expected. These β-peroxylactones are stable and can be useful for further synthetic transformations.

Development of metal-organic framework (MOF)-B12 system as new bio-inspired heterogeneous catalyst

Abstract A novel bimetal complex {Zn4Ru2(bpdc)4·4C2NH8·9DMF}n (1) (H2bpdc = 4,4′-biphenyldicarboxylic acid) was synthesized by the solvothermal method. The results of the X-ray crystallographic analysis revealed that 1 crystallizes in the orthorhombic Pna21 space group, which has a 3D 2-fold interpenetrated hex framework, with open channel sizes along the [010] direction of ca. 1.4 nm × 1.4 nm. The photosensitizer [Ru(bpy)3]2+ was adsorbed into the 1 to form Ru@MOF by cation exchanging. A cobalamin derivative (B12), heptamethyl cobyrinate, was also effectively immobilized on Ru@MOF, and the resulting hybrid complex, B12-Ru@MOF, exhibited a high reactivity for the dechlorination reaction of 1,1-bis(4-chlorophenyl)-2,2,2-trichloroethane (DDT) under an N2 atmosphere by visible light irradiation in the solid state. The catalysis of B12-Ru@MOF can still reach more than a ca. 80% conversion after third recyclings. Furthermore, the heterogeneous catalyst, B12-Ru@MOF, was useful for the cobalamin-dependent reaction, such as the 1,2-migration of the acetyl group.

Enantioselective biocatalytic reduction of 2,2-disubstituted ethylacetoacetates: An indirect desymmetrization approach for the synthesis of enantiopure (S)-4-hydroxy-3,3-disubstituted pentane-2-ones

Ethyl 2,2-disubstituted-3-oxobutanoates were biocatalytically reduced to the corresponding (S)-ethyl 3-hydroxy-2,2-disubstitutedbutanoate with the growing cells of Klebsiella pneumoniae (NBRC 3319) with excellent enantioselection. The biocatalytically derived enantiopure hydroxyl esters were then synthetically manipulated to give (S)-4-hydroxy-3,3-disubstituted pentane-2-ones. The whole process can be regarded as an indirect enantioselective enzymatic desymmetrization method for the synthesis of (S)-4-hydroxy-3,3-disubstituted pentane-2-ones.

Metal-free oxyaminations of alkenes using hydroxamic acids

A radical-mediated approach to metal-free alkene oxyamination is described. This method capitalizes on the unique reactivity of the amidoxyl radical in alkene additions to furnish a general difunctionalization using simple diisopropyl azodicarboxylate (DIAD) as a radical trap. This protocol capitalizes on the intramolecular nature of the process, providing single regioisomers in all cases. Difunctionalizations of cyclic alkenes provide trans oxyamination products inaccessible using current methods with high levels of stereoselectivity, complementing cis-selective oxyamination processes.

Synthesis of enantiomerically enriched α,α-disubstituted β,γ-epoxy esters using hydrolytic kinetic resolution catalyzed by salenCo(III)

Novel α,α-disubstituted epoxy esters were prepared in enantiopure form by hydrolytic kinetic resolution (HKR) of the corresponding racemic mixtures using chiral salenCo(III) as catalyst. The methodology provides a convenient route to enantioenriched β,γ-epoxy esters 2a, 2c and 2d.

The rhodium-catalyzed carbene cyclization cycloaddition cascade reaction of vinylsulfonates

Vinylsulfonates have proved to be excellent dipolarophiles for carbonyl ylides derived from diazoketones in rhodium-catalyzed intramolecular cycloadditions. Polyfunctional substrates, such as 8 and (+)-15, were readily available from hydroxy esters, e.g. 1 and the cyclopenta-1,3-dione 10, respectively, and the resulting polycyclic sultones were formed under mild reaction conditions in high yields with very good diastereoselectivities. A ruthenium-catalyzed asymmetric transfer hydrogenation was found to desymmetrize the meso-cyclopenta-1,3-dione 12 efficiently.

NOVEL CANNABINOID RECEPTOR LIGANDS, PHARMACEUTICAL COMPOSITIONS CONTAINING THEM, AND PROCESSES FOR THEIR PREPARATION

The present invention relates to novel cannabinoid receptor modulators, in particular cannabinoid 1 (CB1) or cannabinoid 2 (CB2) receptor modulators, and uses thereof for treating diseases, conditions and/or disorders modulated by a cannabinoid receptor (such as pain, neurodegenative disorders, eating disorders, weight loss or control, and obesity).

Method for Synthesis of 2,5-Dioxane-1,4-Diones

The invention relates to a novel method for the synthesis of 2,5-dioxane-1,4-diones having formula (I), comprising the oxidation of the ketone function of a cyclic compound having formula (II), wherein R1, R2, R3 and R4 independently represent the hydrogen atom, halo, (C2-C6) alkenyl, (C3-C7)cycloalkyl, cyclohexenyl and a radical having formula —(CH2)m—V—W.