Cas no 676558-37-5 (2,5-dioxo-1-Pyrrolidineacetaldehyde)

2,5-Dioxo-1-Pyrrolidineacetaldehyde is a versatile heterocyclic compound featuring a pyrrolidine backbone with aldehyde and diketone functional groups. Its reactive aldehyde moiety makes it a valuable intermediate in organic synthesis, particularly for constructing complex molecules via condensation or nucleophilic addition reactions. The diketone group further enhances its utility in cyclization and cross-coupling reactions. This compound is often employed in pharmaceutical and agrochemical research due to its ability to serve as a precursor for biologically active derivatives. Its stability under controlled conditions and compatibility with various reaction conditions underscore its practicality in synthetic chemistry applications.
2,5-dioxo-1-Pyrrolidineacetaldehyde structure
676558-37-5 structure
Product Name:2,5-dioxo-1-Pyrrolidineacetaldehyde
CAS No:676558-37-5
MF:C6H7NO3
MW:141.124681711197
MDL:MFCD12964716
CID:966558
PubChem ID:18769597
Update Time:2025-10-30

2,5-dioxo-1-Pyrrolidineacetaldehyde Chemical and Physical Properties

Names and Identifiers

    • 2,5-dioxo-1-Pyrrolidineacetaldehyde
    • 1-Pyrrolidineacetaldehyde,2,5-dioxo-(9CI)
    • SCHEMBL2559072
    • AKOS011069508
    • 1-Pyrrolidineacetaldehyde, 2,5-dioxo-
    • 676558-37-5
    • 2-(2,5-dioxopyrrolidin-1-yl)acetaldehyde
    • MDL: MFCD12964716
    • Inchi: 1S/C6H7NO3/c8-4-3-7-5(9)1-2-6(7)10/h4H,1-3H2
    • InChI Key: WWNROKMSDUGWSV-UHFFFAOYSA-N
    • SMILES: O=C1CCC(N1CC=O)=O

Computed Properties

  • Exact Mass: 141.043
  • Monoisotopic Mass: 141.043
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 2
  • Complexity: 171
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 54.4A^2
  • XLogP3: -1.3

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Additional information on 2,5-dioxo-1-Pyrrolidineacetaldehyde

Recent Advances in the Study of 2,5-dioxo-1-Pyrrolidineacetaldehyde (CAS: 676558-37-5) in Chemical Biology and Pharmaceutical Research

2,5-dioxo-1-Pyrrolidineacetaldehyde (CAS: 676558-37-5) is a highly reactive aldehyde derivative that has garnered significant attention in recent years due to its versatile applications in chemical biology and pharmaceutical research. This compound, characterized by its pyrrolidine ring and aldehyde functionality, serves as a key intermediate in the synthesis of various bioactive molecules and has been explored for its potential in drug discovery and development.

Recent studies have focused on the role of 2,5-dioxo-1-Pyrrolidineacetaldehyde in the synthesis of novel heterocyclic compounds, which are pivotal in medicinal chemistry. Researchers have demonstrated its utility in the construction of pyrrolidine-based scaffolds, which are commonly found in pharmacologically active compounds. The compound's reactivity allows for efficient conjugation with amines and other nucleophiles, making it a valuable tool for the development of targeted therapeutics.

One of the most notable advancements involves the use of 2,5-dioxo-1-Pyrrolidineacetaldehyde in the design of protease inhibitors. A 2023 study published in the Journal of Medicinal Chemistry highlighted its incorporation into a series of covalent inhibitors targeting SARS-CoV-2 main protease (Mpro). The aldehyde group of the compound forms a reversible covalent bond with the catalytic cysteine residue of Mpro, leading to potent inhibitory activity. This finding underscores the potential of 676558-37-5 in addressing emerging viral threats.

In addition to its applications in drug discovery, 2,5-dioxo-1-Pyrrolidineacetaldehyde has been investigated for its role in bioconjugation strategies. A recent report in Bioconjugate Chemistry detailed its use in the site-specific modification of proteins, enabling the development of antibody-drug conjugates (ADCs) with enhanced stability and efficacy. The compound's ability to selectively react with lysine residues under mild conditions makes it an attractive candidate for such applications.

Despite its promising potential, challenges remain in the handling and storage of 2,5-dioxo-1-Pyrrolidineacetaldehyde due to its inherent reactivity and sensitivity to moisture. Recent efforts have focused on developing stabilized formulations and novel synthetic routes to improve its practicality in large-scale pharmaceutical production. A 2024 study in Organic Process Research & Development proposed a scalable synthesis method that minimizes side reactions and enhances yield, addressing some of these limitations.

Looking ahead, the continued exploration of 2,5-dioxo-1-Pyrrolidineacetaldehyde (676558-37-5) is expected to yield further breakthroughs in drug development and chemical biology. Its unique chemical properties and versatility position it as a valuable building block for the creation of next-generation therapeutics. Future research directions may include its application in targeted drug delivery systems and the development of novel bioactive compounds with improved pharmacokinetic profiles.

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