51673-64-4

Usage

Uses

Used in Food and Beverage Industry:
Methyl 3-oxoisobutyrate is used as a flavoring agent for its fruity aroma, enhancing the taste and aroma of various food and beverage products.
Used in Pharmaceutical Industry:
Methyl 3-oxoisobutyrate is used as a precursor in the synthesis of pharmaceuticals, contributing to the development of new medications and therapeutic agents.
Used in Fragrance Industry:
As a precursor, methyl 3-oxoisobutyrate is utilized in the creation of various fragrances, adding to the complexity and richness of scent profiles in perfumes and other scented products.
Used in Polymer Industry:
Methyl 3-oxoisobutyrate serves as a building block in the production of polymers, playing a crucial role in the development of new materials with specific properties for various applications.
Used in Chemical Synthesis:
Methyl 3-oxoisobutyrate is used as a versatile reagent in chemical synthesis, enabling the production of a wide range of different products through its ability to react with various other reagents.

InChI:InChI=1/C5H8O3/c1-4(3-6)5(7)8-2/h3-4H,1-2H3

Upstream product

• 201230-82-2 carbon monoxide 
• 292638-85-8 acrylic acid methyl ester 
• 107-31-3 Methyl formate 
• 554-12-1 propanoic acid methyl ester 
• 7664-93-9 sulfuric acid 
• 40053-01-8 methyl (E)-3-bromo-2-methyl-2-propenoate 
• 3673-79-8 methyl 2,3-dibromoisobutyrate 
• 67-56-1 methanol 
• 759-65-9 diethyl oxalpropionate 
• 76526-43-7 methyl 3,3-dimethoxy-2-methylpropionate 
• 64809-29-6 methyl 3-hydroxy-2-methylpropanoate 
• 82387-34-6 (E)-3-(3-Benzyl-ureido)-2-methyl-acrylic acid methyl ester 
• 82387-35-7 (Z)-3-(3-Benzyl-ureido)-2-methyl-acrylic acid methyl ester 
• 82387-38-0 (E)-3-(3-tert-Butyl-ureido)-2-methyl-acrylic acid methyl ester 

Downstream Products

• 1523-89-3 methyl 1-methyl-4-oxo-2-cyclohexene-1-carboxylate 
• 84607-44-3 2,4,5,6-tetrahydro-6-methoxycarbonyl-6-methyl-3-phenylthio-1-benzofuran-2-one 
• 81470-12-4 2,4,5,6,7,7a-hexahydro-7-hydroxy-6-methoxycarbonyl-6-methyl-3-phenylthio-1-benzofuran-2-one 
• 81470-12-4 2,4,5,6,7,7aα-hexahydro-7β-hydroxy-6β-methoxycarbonyl-6α-methyl-3-phenylthio-1-benzofuran-2-one 
• 81470-12-4 2,4,5,6,7,7aα-hexahydro-7β-hydroxy-6α-methoxycarbonyl-6β-methyl-3-phenylthio-1-benzofuran-2-one 
• 81470-12-4 2,4,5,6,7,7aβ-hexahydro-7β-hydroxy-6α-methoxycarbonyl-6β-methyl-3-phenylthio-1-benzofuran-2-one 
• 72476-02-9 methyl 2-methyl-3-(p-toluenesulfonyloxy)acrylate 
• 1154689-97-0 methyl (E)-2-methyl-3-(p-toluenesulfonyloxy)prop-2-enoate 
• 1188274-47-6 methyl (Z)-2-methyl-3-(p-toluenesulfonyloxy)prop-2-enoate 
• 1224639-65-9 3-{-4-[2-(2,5-dichloro-phenoxy)-5-fluoro-pyridine-3-carbonyl]-3,4-dihydro-2H-quinoxalin-1-yl}-2-methyl-propionic acid 

Relevant academic research and scientific papers

Fast and unprecedented chemoselective hydroformylation of acrylates with a fluoropolymer ligand in supercritical CO2

A fluorous polymeric phosphine, when combined with supercritical CO2 (scCO2) and rhodium, effects fast and highly chemoselective hydroformylation of acrylates, one of the least reactive olefins in hydroformylation reactions.

Catalyst composition containing bidentate phosphine ligand and application thereof

The catalyst composition comprises a bidentate phosphine ligand and a rhodium complex, wherein the skeleton of the bidentate phosphine ligand not only has C. 2 The symmetry and the appropriate rigidity, and the phosphine ligand derived based on the skeleton can provide effective steric hindrance around the catalyst center metal, so that the selectivity of the catalyst can be remarkably improved, the aldehyde yield is not lower 92% when the catalyst combination is applied to the hydroformylation reaction, and the selectivity of n-aldehyde is not lower 90%. In addition, the raw materials olefins with different structures can obtain outstanding reaction rate and normal aldehyde selectivity as compared with the existing catalyst systems, and can be suitable for the hydroformylation reaction of more types of olefins.

Insertion of Alkylidene Carbenes into B-H Bonds

We have developed a protocol for insertion of alkylidene carbenes into the B-H bonds of amine-borane adducts, enabling, for the first time, the construction of C(sp2)-B bonds by means of carbene-insertion reactions. Various acyclic and cyclic alkenyl borane-amine adducts were prepared from readily accessible starting materials in good to high yields and were subsequently subjected to a diverse array of functional group transformations. The unprecedented spiro B-N heterocycles prepared in this study have potential utility as building blocks for the synthesis of pharmaceuticals. Preliminary mechanistic studies suggest that insertion of the alkylidene carbenes into the B-H bonds of the amine-borane adducts proceeds via a concerted process involving a three-membered-ring transition state.

Catalytic isomerization-hydroformylation of olefins by rhodium salicylaldimine pre-catalysts

A series of new Schiff-base rhodium(i) water-soluble complexes (C1-C3), were prepared and characterized. These complexes served as catalyst precursors for the hydroformylation of 1-octene and resulted in excellent substrate conversions (>98%) with 100% chemoselectivities to aldehydes, under mild conditions. Notably, good regioselectivities towards branched aldehydes were observed clearly demonstrating the catalysts’ ability in thermodynamically favoured isomerization followed by hydroformylation (n/iso ratio ranging between 0.7-1.2). Interestingly, catalystC1uniquely promoted contra-thermodynamic isomerization of 2-octene to 1-octene with up to 50% conversion. The efficacy of catalystC1was further evaluated in the hydroformylation of longer chain olefins (C10-C12), methyl acrylate, ethyl acrylate and styrene. The catalyst displayed conversions >99% with the long chain substrates and much lower conversions with the acrylates. These water-soluble (pre)catalysts were recycled up to three times with no significant loss in catalytic activity and selectivity. Mercury poisoning tests were conducted and the experiments revealed that the conversion of the substrates into aldehydes was due to molecular active catalysts and not as a result of colloidal particles that could have formedin situthrough the decomposition of the catalyst precursor. Finally, the molecular catalyst responsible for activity was established using preliminary computational calculations.

Hydroformylation of unsaturated esters and 2,3-dihydrofuran under solventless conditions at room temperature catalysed by rhodium: N-pyrrolyl phosphine catalysts

Rhodium complexes of the type HRh(CO)L3 (where L is an N-pyrrolyl phosphine, such as P(NC4H4)3, PPh(NC4H4)2, or PPh2(NC4H4)) were applied in the hydroformylation of less reactive unsaturated substrates, namely allyl acetate, butyl acrylate, methyl acrylate, 2,3-dihydrofuran and vinyl acetate. Even at room temperature, these catalysts enabled complete substrate conversion and high chemoselectivity towards the corresponding aldehydes. High conversion of vinyl acetate (88% in 6 h) to the branched aldehyde was obtained with HRh(CO)[P(NC4H4)3]3 at 25 °C. An increase of the turnover frequency, TOF, up to 2000 mol mol-1 h-1 was achieved in this reaction under 20 bar of syngas (H2/CO = 1) at 80 °C. The introduction of chiral phosphines, BINAP or Ph-BPE, to this system resulted in the production of a branched aldehyde with enantioselectivity, ee, up to 44 and 81%, respectively. High activity combined with high enantioselectivity was achieved due to the formation of the mixed rhodium hydrides HRh(CO)[P(NC4H4)3](BINAP) and HRh(CO)[P(NC4H4)3](Ph-BPE), identified by the NMR method.

Selective hydroformylation of alkyl acrylates using [2,2′-bis(dipyrrolylphosphinooxy)-1,1′-(±)-binaphthyl]/Rh catalyst: reversal of regioselectivity

The rhodium-catalyzed hydroformylation of alkyl acrylates with different P-N diphosphine ligands is investigated here. Under mild conditions (syngas pressure: 2 MPa, 20 °C), 2,2′-bis(dipyrrolylphosphinooxy)-1,1′-(±)-binaphthyl (L1) rhodium catalyst could give good conversion of ethyl acrylate (82.9%) in 12 h and exclusive branched aldehyde selectivity of >99.0%. More importantly, on elevating the temperature to 90 °C, this Rh system could preferentially afford the linear aldehyde with 96.1% regioselectivity, and the TOF could reach up to 9000 h?1. Deuterioformylation was conducted to explore the mechanism of regioselectivity reversal, and the results established that the reversible rhodium hydride addition to form the Rh-alkyl species might play a vital role in this reversal. The β-hydride elimination of branched Rh-alkyl species was comparatively stronger than that of linear ones under increased temperature, probably because L1 could cause comparatively larger steric repulsion in branched Rh-alkyl species under high temperature, due to its bulky and rigid binaphthyl backbone characteristics. In turn, the linear Rh-alkyl species progress to linear aldehyde was facilitated.

Tandem and One-Pot Hydroformylation/Michael Reactions of Acrylates

The combination of various reactions in one operational step leads to many advantages in synthetic strategies, such as a lower consumption of resources, effort, and time, when intermittent workup and purification steps can be avoided. The hydroformylation reaction of acrylates gives access to 2-formylpropanoates, which thanks to their structural features constitute useful intermediates in the synthesis of more complex compounds. Herein, we report a simple and convenient one-pot strategy to synthesize functionalized carbonyl compounds starting from these readily available substrates, via tandem or one-pot hydroformylation, Michael addition, and aldol reactions.

HETEROCYCLIC MODULATORS OF LIPID SYNTHESIS FOR USE AGAINST CANCER AND VIRAL INFECTIONS

Heterocyclic modulators of lipid synthesis are provided as well as pharmaceutically acceptable salts thereof; pharmaceutical compositions comprising such compounds; and methods of treating conditions characterized by disregulation of a fatly acid synthase pathway by the administration of such compounds. (I)

AMIDO-FLUOROPHOSPHITE COMPOUNDS AND CATALYSTS

Amido-fluorophosphite compounds and catalyst systems comprising at least one amido-fluorophosphite ligand compound in combination with a transition metal are described. Moreover, the use of amido-fluorophosphite containing catalysts for transition metal catalyzed processes, especially to the hydroformylation of various olefins to produce aldehydes are also described.

General, Robust, and stereocomplementary preparation of α,β-disubstituted α,β-unsaturated esters

An (E)- and (Z)-stereocomplementary preparative method for α,β-disubstituted α,β-unsaturated esters Is performed via three general and robust reaction sequences: (i) TI-Claisen condensation (formylation) of esters to give α-formyl esters (12 examples, 60-99%), (II) (E)- and (Z)-stereocomplementary enol ρ-toluenesulfonylation (tosylation) using TsCI-N-methylimidazole (NMI)-Et3N and LiOH (24 examples, 82-99%), and (iii) stereoretentive Suzuki-Miyaura cross-coupling (18 examples, 64-96%).