Cas no 203186-58-7 ((E)-Ethyl 2-((dimethylamino)methylene)-3-oxobutanoate)

(E)-Ethyl 2-((dimethylamino)methylene)-3-oxobutanoate is a versatile β-keto ester derivative with significant utility in organic synthesis. Its key structural features include a reactive enamine moiety and an ester group, making it a valuable intermediate for constructing heterocyclic compounds, particularly pyrazoles and pyrimidines. The compound's stability under ambient conditions and high reactivity in condensation and cyclization reactions enhance its applicability in pharmaceutical and agrochemical research. Its compatibility with a range of nucleophiles and electrophiles allows for efficient derivatization, facilitating the synthesis of complex molecular frameworks. The product is typically supplied in high purity, ensuring reproducibility in synthetic workflows.
(E)-Ethyl 2-((dimethylamino)methylene)-3-oxobutanoate structure
203186-58-7 structure
Product Name:(E)-Ethyl 2-((dimethylamino)methylene)-3-oxobutanoate
CAS No:203186-58-7
MF:C9H15NO3
MW:185.220302820206
MDL:MFCD00087563
CID:1392860
PubChem ID:2763877
Update Time:2025-05-27

(E)-Ethyl 2-((dimethylamino)methylene)-3-oxobutanoate Chemical and Physical Properties

Names and Identifiers

    • Butanoic acid, 2-[(dimethylamino)methylene]-3-oxo-, ethyl ester, (2E)-
    • (E)-Ethyl 2-((dimethylamino)methylene)-3-oxobutanoate
    • ethyl 2-(dimethylaminomethylidene)-3-oxobutanoate
    • ethyl(E)-2-((dimethylamino)methylene)-3-oxobutanoate
    • 203186-58-7
    • AC-23241
    • Ethyl 2-[(dimethylamino)methylidene]-3-oxobutanoate
    • ETHYL (2E)-2-ACETYL-3-(DIMETHYLAMINO)ACRYLATE
    • AKOS005070346
    • ethyl (2E)-2-(dimethylaminomethylidene)-3-oxobutanoate
    • CS-W005704
    • ethyl 2-dimethylaminomethylene-3-oxobutanoate
    • LQSOVGAUOHMPLK-SOFGYWHQSA-N
    • AKOS025310760
    • EN300-126850
    • LS-13671
    • 4F-012
    • A920777
    • A7561
    • J-502001
    • ethyl (2E)-2-[(dimethylamino)methylidene]-3-oxobutanoate
    • CS-0449689
    • Ethyl (E)-2-((dimethylamino)methylene)-3-oxobutanoate
    • MFCD00087563
    • 2-[1-dimethylamino-methylidene]-3-oxo-butyric acid ethyl ester
    • 51145-57-4
    • AM20100255
    • 2-acetyl-3-dimethylamino-acrylic acid ethyl ester
    • (E)-ethyl 2-((dimethylamino)methylene)-3-oxobutanoate;Ethyl 2-((dimethylamino)methylene)-3-oxobutanoate
    • Ethyl N,N-dimethylaminomethylene acetoacetate
    • ethyl 2-acetyl-3-(dimethylamino)acrylate
    • Ethyl 2-((dimethylamino)methylene)-3-oxobutanoate
    • (E)-ethyl2-((dimethylamino)methylene)-3-oxobutanoate
    • MDL: MFCD00087563
    • Inchi: 1S/C9H15NO3/c1-5-13-9(12)8(7(2)11)6-10(3)4/h6H,5H2,1-4H3/b8-6+
    • InChI Key: LQSOVGAUOHMPLK-SOFGYWHQSA-N
    • SMILES: O(CC)C(/C(/C(C)=O)=C/N(C)C)=O

Computed Properties

  • Exact Mass: 185.10500
  • Monoisotopic Mass: 185.10519334g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 5
  • Complexity: 231
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 1
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 0.7
  • Topological Polar Surface Area: 46.6?2

Experimental Properties

  • Color/Form: Liquid
  • PSA: 46.61000
  • LogP: 0.58400

(E)-Ethyl 2-((dimethylamino)methylene)-3-oxobutanoate Security Information

(E)-Ethyl 2-((dimethylamino)methylene)-3-oxobutanoate Pricemore >>

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(E)-Ethyl 2-((dimethylamino)methylene)-3-oxobutanoate Production Method

Additional information on (E)-Ethyl 2-((dimethylamino)methylene)-3-oxobutanoate

Recent Advances in the Study of (E)-Ethyl 2-((dimethylamino)methylene)-3-oxobutanoate (CAS: 203186-58-7) and Its Applications in Chemical Biology and Pharmaceutical Research

(E)-Ethyl 2-((dimethylamino)methylene)-3-oxobutanoate (CAS: 203186-58-7) is a key intermediate in the synthesis of various heterocyclic compounds, which are of significant interest in medicinal chemistry and drug discovery. Recent studies have highlighted its utility in the development of novel bioactive molecules, particularly in the fields of oncology, infectious diseases, and neurological disorders. This research briefing aims to summarize the latest findings related to this compound, focusing on its synthetic applications, biological activities, and potential therapeutic implications.

One of the most notable advancements in the use of (E)-Ethyl 2-((dimethylamino)methylene)-3-oxobutanoate is its role in the synthesis of pyrazole and pyrimidine derivatives. These heterocycles are known for their diverse pharmacological properties, including anti-inflammatory, antimicrobial, and anticancer activities. A 2023 study published in the Journal of Medicinal Chemistry demonstrated that derivatives synthesized using this compound exhibited potent inhibitory effects against several cancer cell lines, with IC50 values in the low micromolar range. The study also identified specific structural modifications that enhance binding affinity to target proteins, such as kinases and histone deacetylases.

In addition to its applications in oncology, (E)-Ethyl 2-((dimethylamino)methylene)-3-oxobutanoate has been explored as a building block for antiviral agents. Recent research has shown that its incorporation into nucleoside analogs can improve their pharmacokinetic properties and reduce off-target effects. For instance, a 2022 study in Antiviral Research reported the successful synthesis of a series of ribavirin analogs using this compound, which displayed enhanced activity against RNA viruses, including SARS-CoV-2 and influenza. These findings underscore the potential of this intermediate in addressing emerging viral threats.

Another area of interest is the compound's role in neuropharmacology. A 2023 preprint on bioRxiv described the use of (E)-Ethyl 2-((dimethylamino)methylene)-3-oxobutanoate in the development of small-molecule modulators of glutamate receptors. These modulators showed promise in preclinical models of neurodegenerative diseases, such as Alzheimer's and Parkinson's, by selectively targeting NMDA and AMPA receptors. The study also highlighted the compound's favorable safety profile and bioavailability, making it a viable candidate for further drug development.

From a synthetic chemistry perspective, recent advancements have focused on optimizing the yield and purity of (E)-Ethyl 2-((dimethylamino)methylene)-3-oxobutanoate. A 2023 paper in Organic Process Research & Development detailed a scalable, green chemistry approach using catalytic amounts of Lewis acids, which reduced waste and improved efficiency. This method is particularly relevant for industrial-scale production, where cost-effectiveness and environmental impact are critical considerations.

In conclusion, (E)-Ethyl 2-((dimethylamino)methylene)-3-oxobutanoate (CAS: 203186-58-7) continues to be a versatile and valuable intermediate in chemical biology and pharmaceutical research. Its applications span multiple therapeutic areas, and ongoing studies are likely to uncover additional uses for this compound. Future research should focus on elucidating its mechanism of action in various biological systems and exploring its potential in combination therapies. The compound's adaptability and efficacy make it a promising candidate for the next generation of bioactive molecules.

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