3249-68-1

Usage

Uses

1. Used in Pharmaceutical Synthesis:
Ethyl butyrylacetate is used as a key intermediate in the synthesis of pharmaceutical agents, such as the anti-HIV agent (+/-)-Calanolide A. It plays a crucial role in the development of this medication due to its unique chemical properties.
2. Used in the Synthesis of Polymerase Inhibitors:
Ethyl butyrylacetate is also utilized in the synthesis of potent and selective polymerase inhibitors. These inhibitors are essential in the development of treatments for various diseases, including viral infections.
3. Used in Flavor and Fragrance Industry:
Ethyl butyrylacetate is used as a flavoring agent for its fruity, pineapple, and green taste with sweet licorice and vanilla notes. It is particularly suitable for the creation of artificial fruit flavors, enhancing the taste and aroma of various food products.
4. Used in the Perfumery Industry:
Due to its slightly fatty odor and unique scent profile, Ethyl butyrylacetate is employed in the perfumery industry to create and enhance various fragrances, adding depth and complexity to the final product.

Synthesis Reference(s)

The Journal of Organic Chemistry, 44, p. 310, 1979 DOI: 10.1021/jo01316a039

InChI:InChI=1/C8H14O3/c1-3-5-7(9)6-8(10)11-4-2/h3-6H2,1-2H3

Upstream product

• 63765-76-4 ethyl 3-oxo-2-acetylhexanoate 
• 141-78-6 ethyl acetate 
• 105-54-4 butanoic acid ethyl ester 
• 21633-79-4 Butyrylmalonsaeure-diethylester 
• 623-73-4 diazoacetic acid ethyl ester 
• 123-72-8 butyraldehyde 
• 64-17-5 ethanol 
• 66696-77-3 5-(1-hydroxybutylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 105-58-8 Diethyl carbonate 
• 73295-48-4 ethyl 2-diazo-3-hydroxyhexanoate 
• 107-87-9 2-Pentanone 
• 107-08-4 1-iodo-propane 
• 105-56-6 ethyl 2-cyanoacetate 
• 72139-59-4 3-(Ethoxycarbonylamino)-2-hexensaeure-ethylester 

Downstream Products

• 66346-53-0 5-hydroxy-7-methyl-4-propylcoumarin 
• 29304-40-3 2-methyl-3-oxohexanoic acid ethyl ester 
• 66346-59-6 5,7-dihydroxy-4-propylcoumarin 
• 3855-85-4 6,8-Dibrom-coumaryl-3-propylketon 
• 21918-19-4 2-phenyl-5-propyl-2H-pyrazole-3,4-dione-4-oxime 
• 57816-83-8 (8-ethyl-1-propyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid 
• 13505-35-6 Undecandion-(4,8) 
• 72817-86-8 4-Amino-5-cyan-3-ethyl-salicylsaeure-ethylester 
• 85111-47-3 2-ethyl-3,5,5-trimethylcyclohex-2-en-1-one 
• 52452-41-2 4-Ethoxy-3-ethyl-6-methyl-2-oxo-cyclohex-3-enecarboxylic acid ethyl ester 
• 92494-37-6 3-(2-chloro-phenyl)-5-propyl-isoxazole-4-carboxylic acid ethyl ester 
• 67187-93-3 (E)-3-(4-Acetylamino-2,5-dimethoxy-phenylamino)-hex-2-enoic acid ethyl ester 
• 92029-30-6 3-phenyl-5-propyl-isoxazole-4-carboxylic acid 
• 93735-65-0 N-Aethyl-N-<4-oxo-heptyl>-phenaethylamin 

Relevant academic research and scientific papers

Charge-directed conjugate addition reactions of salts of unsaturated β-keto-esters

Strong nucleophiles undergo conjugate addition reactions with enolates of Nazarov-type reagents. Yields are strongly affected by substitution patterns and the metal cation employed.

Discrimination of β-ketoesters by ruthenium(II)-binap-catalyzed asymmetric hydrogenation

(Chemical Equation Presented) Please, after you... β-Ketoesters in mixtures underwent Noyori reduction one by one at room temperature under 4 bar of hydrogen pressure in the presence of a catalyst formed from RuII and (S)-binap (see example). The rate of the asymmetric hydrogenation and hence the selectivity for a particular β-ketoester was found to depend on the Lewis basicity of the ester group. Binap = 2,2′-bis(diphenylphosphanyl)-1, 1′-binaphthyl.

Radical Aza-Cyclization of α-Imino-oxy Acids for Synthesis of Alkene-Containing N-Heterocycles via Dual Cobaloxime and Photoredox Catalysis

Nitrogen-containing heterocycles are prevalent in both naturally and synthetically bioactive molecules. We report herein an unprecedented protocol for radical aza-cyclization of α-imino-oxy acids with pendant alkenes via synergistic photoredox and cobaloxime catalysis. With or without alkenes as the intermolecular cross-coupling partners, the transformation provides a variety of corresponding alkene-containing dihydropyrrole products in satisfactory yields. In the presence of external alkenes, the tandem reaction generates E-selective coupling products with excellent chemo- and stereoselectivity.

Desymmetrization of meso-dicarbonatecyclohexene with β-Hydrazino carboxylic esters via a Pd-catalyzed allylic substitution cascade

The desymmetrization of meso-dicarbonatecyclohexene with β-hydrazino carboxylic esters has been achieved via a RuPHOX/Pd-catalyzed allylic substitution cascade for the construction of chiral hexahydrocinnoline derivatives with high performance. Mechanistic studies reveal that the reaction exploits a pathway different from that of our previous work and that the first nitrogen nucleophilic process is the rate-determining step. The protocol could be conducted on a gram scale without any loss of catalytic behavior, and the corresponding chiral hexahydrocinnolines can undergo diverse transformations.

Synthesis of Long-Chain β-Lactones and Their Antibacterial Activities against Pathogenic Mycobacteria

In the quest for new antibacterial agents, a series of novel long- and medium-chain mono- and disubstituted β-lactones was developed. Their activity against three pathogenic mycobacteria—M. abscessus, M. marinum, and M. tuberculosis—was assessed by the resazurin microtiter assay (REMA). Among the 16 β-lactones synthesized, only 3-hexadecyloxetan-2-one (VM005) exhibited promising activity against M. abscessus, whereas most of the β-lactones showed interesting activities against M. marinum, similar to that of the classical antibiotic, isoniazid. Regarding M. tuberculosis, six compounds were found to be active against this mycobacterium, with β-lactone VM008 [trans-(Z)-3-(hexadec-7-en-1-yl)-4-propyloxetan-2-one] being the best growth inhibitor. The promising antibacterial activities of the best compounds in this series suggest that these molecules may serve as leads for the development of much more efficient antimycobacterial agents.

General [4 + 1] Cyclization Approach to Access 2,2-Disubstituted Tetrahydrofurans Enabled by Electrophilic Bifunctional Peroxides

A general [4 + 1] cyclization reaction of carbonyl nucleophiles with 2-iodomethylallyl peroxides, which function as unique electrophilic oxygen synthons, for the synthesis of a broad range of 2,2-disubstituted tetrahydrofurans is achieved under operationally simple conditions. The unprecedented asymmetric version of such reaction is also realized via chiral auxiliary-assisted cyclization, thus providing a distinct approach to access chiral tetrahydrofurans with high diastereoselectivities. The new method can be applied to the synthesis of core structure of posaconazole drug.

Continuous flow synthesis of toxic ethyl diazoacetate for utilization in an integrated microfluidic system

An integrated microfluidic system for multiple reactions and separations of hazardous ethyl diazoacetate is presented. The integrated techniques include: a droplet technique for liquid-liquid and/or gas-liquid separation and in situ generation of the toxic reagent, a dual channel membrane technique based on a cheap polymeric microseparator for liquid-liquid separation, and a capillary microreactor for carrying out cascade reactions in a sequential and continuous manner.

Tert-BuOK-Catalyzed condensation of ethyl diazoacetate to aldehydes and palladium-catalyzed 1,2-hydrogen migration for the synthesis of β-ketoesters under solvent-free conditions

A mild and convenient method for the condensation of ethyl diazoacetate (EDA) with aldehydes catalyzed by tert-BuOK under solvent-free conditions was developed. The corresponding α-diazo-β-hydroxy esters were further converted into β-ketoesters through palladium-catalyzed 1,2-hydrogen migration under neat conditions. The two-step transformation exemplifies a simple method for the efficient and green synthesis of β-ketoesters. The Royal Society of Chemistry 2013.

Chemoenzymatic asymmetric synthesis of pregabalin precursors via asymmetric bioreduction of β-cyanoacrylate esters using ene-reductases

The asymmetric bioreduction of a library of β-cyanoacrylate esters using ene-reductases was studied with the aim to provide a biocatalytic route to precursors for GABA analogues, such as pregabalin. The stereochemical outcome could be controlled by substrate-engineering through size-variation of the ester moiety and by employing stereochemically pure (E)- or (Z)-isomers, which allowed to access both enantiomers of each product in up to quantitative conversion in enantiomerically pure form. In addition, stereoselectivities and conversions could be improved by mutant variants of OPR1, and the utility of the system was demonstrated by preparative-scale applications.

PYRROLE CARBOXYLIC ACID DERIVATIVES AS ANTIBACTERIAL AGENTS

The present invention provides DNA Gyrase and/or Topo IV inhibitors of Formula (I), which can be used as antibacterial agents. Compounds disclosed herein can be used for treating or preventing conditions caused by or contributed by gram positive, gram negative and anaerobic bacteria, more particularly against, for example, Staphylococci, Streptococci, Enterococci, Haemophilus, Pseudomonus spp., Acenetobacter spp., Mvraxalla spp., Chlamydia spp., Mycoplasma spp., Legionella spp., Mycobacterium spp., Helicobacter, Clostridium spp., Bacteroides spp., Cotynebacterium, Bacillus spp., Enterobactericeae (E. coli, Klebsiella spp., Proteus spp., etc.) or any combination thereof. Also provided, are processes for preparing compounds disclosed herein, pharmaceutical compositions containing compounds disclosed herein, and methods of treating bacterial infections.