Cas no 257883-97-9 (ethyl 3-oxooxetane-2-carboxylate)

Ethyl 3-oxooxetane-2-carboxylate is a versatile oxetane derivative characterized by its reactive ketone and ester functional groups. This compound serves as a valuable building block in organic synthesis, particularly for the preparation of heterocyclic compounds and pharmaceutical intermediates. Its strained oxetane ring enhances reactivity, enabling efficient ring-opening reactions and cycloadditions. The ester moiety offers further derivatization potential, while the ketone group facilitates nucleophilic additions and condensations. The compound's stability under standard conditions and compatibility with a range of solvents make it suitable for diverse synthetic applications. Its structural features are advantageous in medicinal chemistry for designing bioactive molecules with improved metabolic stability.
ethyl 3-oxooxetane-2-carboxylate structure
257883-97-9 structure
Product Name:ethyl 3-oxooxetane-2-carboxylate
CAS No:257883-97-9
MF:C6H8O4
MW:144.125322341919
CID:246990
PubChem ID:45090013
Update Time:2025-10-31

ethyl 3-oxooxetane-2-carboxylate Chemical and Physical Properties

Names and Identifiers

    • 2-Oxetanecarboxylicacid, 3-oxo-, ethyl ester
    • 2-Oxetanecarboxylicacid,3-oxo-,ethylester(9CI)
    • ethyl 3-oxooxetane-2-carboxylate
    • EN300-6738973
    • Ethyl3-oxooxetane-2-carboxylate
    • 257883-97-9
    • Inchi: 1S/C6H8O4/c1-2-9-6(8)5-4(7)3-10-5/h5H,2-3H2,1H3
    • InChI Key: MOCCKUWMECSVEO-UHFFFAOYSA-N
    • SMILES: O1CC(C1C(=O)OCC)=O

Computed Properties

  • Exact Mass: 144.042
  • Monoisotopic Mass: 144.042
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 3
  • Complexity: 163
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 1
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 52.6A^2
  • XLogP3: 0.2

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Additional information on ethyl 3-oxooxetane-2-carboxylate

Introduction to Ethyl 3-Oxo-Oxetane-2-Carboxylate (CAS No. 257883-97-9)

Ethyl 3-oxooxetane-2-carboxylate, with the chemical identifier CAS No. 257883-97-9, is a significant compound in the realm of organic chemistry and pharmaceutical research. This compound belongs to the class of oxetane derivatives, which are known for their unique structural properties and versatile applications in synthetic chemistry and drug development.

The molecular structure of ethyl 3-oxooxetane-2-carboxylate features a cyclic ether backbone with a carboxylate ester group and a ketone moiety. This configuration makes it a valuable intermediate in the synthesis of more complex molecules, particularly in the pharmaceutical industry. The oxetane ring itself is highly reactive, allowing for various functionalization strategies that can be tailored to specific chemical needs.

In recent years, there has been growing interest in oxetane derivatives due to their potential applications in medicinal chemistry. The reactivity of the oxetane ring allows for facile opening under controlled conditions, making it an excellent scaffold for constructing biologically active molecules. For instance, studies have demonstrated the utility of ethyl 3-oxooxetane-2-carboxylate in the synthesis of novel heterocyclic compounds that exhibit promising pharmacological properties.

One of the most intriguing aspects of ethyl 3-oxooxetane-2-carboxylate is its role as a precursor in the development of enzyme inhibitors. The oxetane core can be modified to target specific binding sites on enzymes, thereby modulating their activity. This has led to several research initiatives aimed at identifying new therapeutic agents for various diseases. The compound's ability to undergo regioselective reactions makes it particularly useful in designing molecules with high specificity and low toxicity.

The synthesis of ethyl 3-oxooxetane-2-carboxylate typically involves multi-step reactions that require precise control over reaction conditions. Common methods include the condensation of ethyl acetoacetate with epichlorohydrin, followed by subsequent functionalization to introduce the desired substituents. Advances in synthetic methodologies have enabled more efficient and scalable production processes, making this compound more accessible for industrial applications.

In the context of drug discovery, ethyl 3-oxooxetane-2-carboxylate has been explored as a building block for peptidomimetics. Peptidomimetics are designed to mimic the biological activity of peptides but with improved stability and pharmacokinetic properties. The oxetane ring can be incorporated into peptidomimetic structures to enhance binding affinity and selectivity. This approach has shown promise in developing treatments for neurological disorders, where peptide-based therapies face challenges related to bioavailability and degradation.

The chemical reactivity of ethyl 3-oxooxetane-2-carboxylate also makes it a valuable tool in materials science. Researchers have utilized this compound to develop novel polymers with unique properties, such as biodegradability and mechanical strength. These polymers find applications in medical devices, where biocompatibility is paramount. The ability to functionalize the oxetane ring allows for the creation of materials with tailored characteristics, making them suitable for diverse industrial uses.

In summary, ethyl 3-oxooxetane-2-carboxylate (CAS No. 257883-97-9) is a versatile compound with significant implications in pharmaceuticals and materials science. Its unique structural features and reactivity make it an indispensable tool for synthetic chemists and researchers working on drug development. As our understanding of organic chemistry continues to evolve, the applications of such compounds are likely to expand, offering new solutions to complex scientific challenges.

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