4949-44-4

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl propionylacetate is used as an intermediate for the synthesis of Rosuvastatin, a widely prescribed medication for lowering cholesterol levels in patients with hyperlipidemia.
Used in Chemical Synthesis:
Ethyl propionylacetate is used as a precursor in the preparation of 1-ethyland 1-n-propyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid, which are compounds bearing one or two substituents on the benzene ring. These compounds have potential applications in various fields, including pharmaceuticals and materials science.
Used in Organic Chemistry:
Ethyl propionylacetate is utilized in the synthesis of 3-propionyl-2H-cyclohepta[b]furan-2-one, a compound that can be further modified or used as a building block for the development of new organic molecules with diverse applications.

InChI:InChI=1/C7H12O3/c1-3-6(8)5-7(9)10-4-2/h3-5H2,1-2H3

Upstream product

• 39580-00-2 1,1-dichloro-pent-1-en-3-one 
• 141-52-6 sodium ethanolate 
• 60-29-7 diethyl ether 
• 79-03-8 propionyl chloride 
• 141-78-6 ethyl acetate 
• 21633-77-2 diethyl 2-propionylmalonate 
• 802294-64-0 propionic acid 
• 10467-10-4 ethylmagnesium iodide 
• 105-56-6 ethyl 2-cyanoacetate 
• 64-17-5 ethanol 
• 77570-18-4 5-(1-Amino-propylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dione 
• 105-53-3 diethyl malonate 
• 141-97-9 ethyl acetoacetate 
• 74-88-4 methyl iodide 

Downstream Products

• 104439-88-5 5-ethyl-2-methyl-1-phenyl-1,2-dihydro-pyrazol-3-one 
• 67244-24-0 ethyl 2-propyl-propionylacetate 
• 53939-83-6 6-ethyl-2,3-dihydro-2-thioxopyrimidin-4(1H)-one 
• 916319-06-7 5-ethyl-2-phenyl-1,2-dihydro-pyrazol-3-one 
• 37013-86-8 ethyl 4-acetyl-3-ethyl-5-methyl-1H-pyrrole-2-carboxylate 
• 20935-29-9 2-methyl-3-[4-(methoxy)phenyl]cyclopent-2-ene-1-one 
• 71-23-8 propan-1-ol 
• 144-62-7 oxalic acid 
• 5734-66-7 2-amino-6-ethylpyrimidin-4-ol 
• 83909-24-4 2,4-Dimethyl-3,5-diphenyl-2-cyclohexen-1-on 
• 5734-66-7 6-ethylisocytosine 
• 34042-00-7 (2SR,3RS)-2-amino-3-hydroxypentanoic acid 
• 32493-32-6 methyl (2-ethyl)propionylacetate 
• 3222-61-5 3-amino-pent-2-enoic acid ethyl ester 

Relevant academic research and scientific papers

Enones with Strained Double Bonds. 5. The 2-Methylbicyclonon-1-en-3-one System

Reaction of the bromo ketone 8 with Et3N resulted in the generation of solutions containing the strained enone 9.Enone 9 could be trapped with furan to form Diels-Alder adducts 10 and 11.However, enone 9 was consumed more rapidly in a reaction that formed the dimeric diketone 12.This dimeric product 12 is believed to be formed by an ene reaction (see structure 14) that occurs under mild conditions.

Screening, synthesis, crystal structure, and molecular basis of 6-amino-4-phenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles as novel AKR1C3 inhibitors

AKR1C3 is a promising therapeutic target for castration-resistant prostate cancer. Herein, an evaluation of in-house library discovered substituted pyranopyrazole as a novel scaffold for AKR1C3 inhibitors. Preliminary SAR exploration identified its derivative 19d as the most promising compound with an IC50 of 0.160 μM among the 23 synthesized molecules. Crystal structure studies revealed that the binding mode of the pyranopyrazole scaffold is different from the current inhibitors. Hydroxyl, methoxy and nitro group at the C4-phenyl substituent together anchor the inhibitor to the oxyanion site, while the core of the scaffold dramatically enlarges but partially occupies the SP pockets with abundant hydrogen bond interactions. Strikingly, the inhibitor undergoes a conformational change to fit AKR1C3 and its homologous protein AKR1C1. Our results suggested that conformational changes of the receptor and the inhibitor should both be considered during the rational design of selective AKR1C3 inhibitors. Detailed binding features obtained from molecular dynamics simulations helped to finally elucidate the molecular basis of 6-amino-4-phenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles as AKR1C3 inhibitors, which would facilitate the future rational inhibitor design and structural optimization.

General, Simple, and Chemoselective Catalysts for the Isomerization of Allylic Alcohols: The Importance of the Halide Ligand

Remarkably simple IrIIIcatalysts enable the isomerization of primary and sec-allylic alcohols under very mild reaction conditions. X-ray absorption spectroscopy (XAS) and mass spectrometry (MS) studies indicate that the catalysts, with the general formula [Cp*IrIII], require a halide ligand for catalytic activity, but no additives or additional ligands are needed.

PROCESS FOR ACYL-TRANSFER ENZYME REACTIONS WITH ACYL- COENZYME A

The present invention relates to a method for acyltransferase reaction in which an acyl group of acyl coenzyme A is transferred to an acyl group receptor characterized in that the reaction is carried out by production and/or reproduction of acyl coenzyme A from coenzyme A in a reaction system by a chemical thioester exchange reaction with acylthioester. The present invention, wherein expensive acyl CoA is reproduced nonenzymatically in a reaction system, enables to continuously carry out acyltransferase reaction only by putting a small amount of acyl CoA with a donor and a receptor of an acyl group into a system. Accordingly, the method of the present invention can be applied to an industrial production method of various kinds of compounds including useful biological molecules and synthesis of polymers such as polyester.

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.

Syntheses and pyrolyses of furan analogues of α-Oxo- o -quinodimethanes. Formation of methylenecyclobutenone and 1-buten-3-yne via a vinylcarbene-cyclopropene rearrangement

Flash vacuum pyrolyses (FVP) of benzoic 2-methyl-3-furoic anhydride (12) and benzoic 3-methyl-2-furoic anhydride (13) at 550 °C and ca. 10 -2 Torr both give methylenecyclobutenone (16) and 1-buten-3-yne (17) as the main products. A mechanism involving generation of furan analogues of α-oxo-o-quinodimethane, 10 and 11, from FVP of 12 and 13, respectively, followed by elimination of a CO molecule to give the respective carbenes 34 and 36 is proposed. Carbenes 34 and 36 are interconvertible via a cyclopropene intermediate 35. A ring contraction from 36 will give 16, whereas a ring-opening of 34 followed by elimination of a CO molecule then leads to 17. The proposed mechanism is supported by substituent- and deuterium-labeling study on FVP of the derivatives of 12.

A facile synthesis of α-fluoro ketones catalyzed by [Cp*IrCl2]2

Allylic alcohols are isomerized into enolates (enols) by [Cp*IrCl2]2. The enolates react with Selectfluor present in the reaction media. This method produces α-fluoro ketones as single constitutional isomers in high yields. Georg Thieme Verlag Stuttgart. New York.

CuSO4-catalyzed diazo decomposition in water: a practical synthesis of β-keto esters

CuSO4 was found to be an efficient catalyst for the diazo decomposition of β-hydroxy α-diazoesters in water. 1,2-H shift occurred efficiently to give β-keto esters in high yields. No O-H bond insertion products were identified.

Microwave assisted rapid and efficient synthesis of aryl methyl ketones and β-keto esters using Meldrum's acid

Microwave mediated rapid and efficient synthesis of aryl methyl ketones and β-keto esters from acyl Meldrum's acid by hydrolysis and alcoholysis, respectively, has been reported.

Synthesis and evaluation of the molluscicidal activity of the 5,6-dimethyl-dihydro-pyran-2,4-dione and 6-substituted analogous

Five dihydro-piran-2,4-diones, including 5,6-dimethyl-dihydro-piran-2,4- dione one of the intermediates of the synthesis of caloverticilic acid, were synthesized and submitted to molluscicidal bioassay. The compound's yields varied from moderate to good (42%- 80%) and were achieved through the preparation of the dianion of ethyl acetoacetate, reaction with and aldehyde followed by hydrolysis of the ester (NaOH, H2O, 2 h, T.A.) and lactonization in acidic medium (HCl, 0°C). The 5,6-dimethyl-dihydro-piran-2, 4-dione and three analogous dihydro-piran-2,4-diones 6-substituted,-phenyl, (4-methoxy-phenyl), and -propenyl, showed significant activities against the Biomphalaria glabrata egg masses, while the analogous 6-(3,4-dimethoxy-phenyl) was inactive as molluscicide. This activity is reported for the first time, extending the range of biological activities of this group.