Cas no 1105663-94-2 (1-Tert-butyl 3-ethyl 3-carbamoylazetidine-1,3-dicarboxylate)

1-Tert-butyl 3-ethyl 3-carbamoylazetidine-1,3-dicarboxylate is a versatile azetidine-based building block used in organic synthesis and pharmaceutical research. Its bifunctional carboxylate groups and carbamoyl moiety enable selective modifications, making it valuable for constructing complex heterocyclic frameworks. The tert-butyl and ethyl ester groups provide orthogonal protection, facilitating stepwise derivatization under mild conditions. This compound is particularly useful in medicinal chemistry for the development of bioactive molecules, owing to its rigid azetidine core, which can enhance metabolic stability and conformational control. High purity and well-defined reactivity further ensure reproducibility in synthetic applications. Its structural features make it a practical intermediate for targeting diverse therapeutic scaffolds.
1-Tert-butyl 3-ethyl 3-carbamoylazetidine-1,3-dicarboxylate structure
1105663-94-2 structure
Product Name:1-Tert-butyl 3-ethyl 3-carbamoylazetidine-1,3-dicarboxylate
CAS No:1105663-94-2
MF:C12H20N2O5
MW:272.297603607178
MDL:MFCD28401681
CID:4560739
PubChem ID:59558379
Update Time:2025-08-03

1-Tert-butyl 3-ethyl 3-carbamoylazetidine-1,3-dicarboxylate Chemical and Physical Properties

Names and Identifiers

    • 1-tert-butyl 3-ethyl 3-carbamoylazetidine-1,3-dicarboxylate
    • AMY34646
    • SB22517
    • 1-Boc-3-carbamoyl-3-carbethoxyazetidine
    • 1-t-Butyl 3-ethyl 3-carbamoylazetidine-1,3-dicarboxylate
    • 1-O-tert-butyl 3-O-ethyl 3-carbamoylazetidine-1,3-dicarboxylate
    • 3-Carbamoyl-azetidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester
    • 1-(1,1-Dimethylethyl) 3-ethyl 3-(aminocarbonyl)-1,3-azetidinedicarboxylate
    • AS-53446
    • Ethyl 3-Carbamoyl-1-Boc-azetidine-3-carboxylate
    • SY099731
    • CS-0052384
    • P16502
    • TYHWSMCZSPERFP-UHFFFAOYSA-N
    • MFCD28401681
    • DTXSID001144833
    • 1-(tert-butyl) 3-ethyl 3-carbamoylazetidine-1,3-dicarboxylate
    • 1105663-94-2
    • DB-389925
    • SCHEMBL428115
    • 1-tert-butyl3-ethyl3-carbamoylazetidine-1,3-dicarboxylate
    • AKOS030627940
    • 1-Tert-butyl 3-ethyl 3-carbamoylazetidine-1,3-dicarboxylate
    • MDL: MFCD28401681
    • Inchi: 1S/C12H20N2O5/c1-5-18-9(16)12(8(13)15)6-14(7-12)10(17)19-11(2,3)4/h5-7H2,1-4H3,(H2,13,15)
    • InChI Key: TYHWSMCZSPERFP-UHFFFAOYSA-N
    • SMILES: O(C(C)(C)C)C(N1CC(C(=O)OCC)(C(N)=O)C1)=O

Computed Properties

  • Exact Mass: 272.13722174 g/mol
  • Monoisotopic Mass: 272.13722174 g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 19
  • Rotatable Bond Count: 6
  • Complexity: 393
  • 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
  • XLogP3: 0
  • Topological Polar Surface Area: 98.9
  • Molecular Weight: 272.30

1-Tert-butyl 3-ethyl 3-carbamoylazetidine-1,3-dicarboxylate Pricemore >>

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Additional information on 1-Tert-butyl 3-ethyl 3-carbamoylazetidine-1,3-dicarboxylate

Recent Advances in the Application of 1-Tert-butyl 3-ethyl 3-carbamoylazetidine-1,3-dicarboxylate (CAS: 1105663-94-2) in Chemical Biology and Pharmaceutical Research

The compound 1-Tert-butyl 3-ethyl 3-carbamoylazetidine-1,3-dicarboxylate (CAS: 1105663-94-2) has emerged as a key intermediate in the synthesis of bioactive molecules and pharmaceutical agents. Recent studies have highlighted its utility in the development of novel therapeutic candidates, particularly in the areas of protease inhibition and targeted drug delivery. This research brief synthesizes the latest findings on this compound, focusing on its chemical properties, synthetic applications, and potential therapeutic implications.

In a 2023 study published in the Journal of Medicinal Chemistry, researchers demonstrated the efficacy of 1-Tert-butyl 3-ethyl 3-carbamoylazetidine-1,3-dicarboxylate as a precursor in the synthesis of selective cathepsin inhibitors. The compound's unique azetidine scaffold and carboxylate functionalities were leveraged to enhance binding affinity and selectivity, resulting in inhibitors with improved pharmacokinetic profiles. This work underscores the compound's potential in addressing unmet medical needs in inflammatory and oncological diseases.

Further investigations have explored the compound's role in PROTAC (Proteolysis Targeting Chimera) development. A recent Nature Chemical Biology publication (2024) detailed its incorporation into bifunctional molecules designed to target undruggable proteins. The tert-butyl and ethyl ester groups were found to provide optimal linker geometry for E3 ligase recruitment, while the carbamoyl moiety contributed to target protein engagement. These findings position 1105663-94-2 as a valuable building block in next-generation targeted protein degradation strategies.

From a synthetic chemistry perspective, advances in the scalable production of 1-Tert-butyl 3-ethyl 3-carbamoylazetidine-1,3-dicarboxylate have been reported. A 2024 Organic Process Research & Development article described an improved catalytic asymmetric synthesis route with 92% enantiomeric excess, addressing previous challenges in stereocontrol. This methodological breakthrough has significant implications for the cost-effective production of chiral pharmaceuticals derived from this intermediate.

Emerging applications in radiopharmaceuticals have also been documented. The compound's ability to serve as a chelator scaffold for diagnostic radionuclides was demonstrated in recent preclinical studies (European Journal of Nuclear Medicine and Molecular Imaging, 2024). When functionalized with gallium-68 or copper-64, derivatives showed promising tumor-targeting capabilities in PET imaging, suggesting potential theranostic applications.

In conclusion, 1-Tert-butyl 3-ethyl 3-carbamoylazetidine-1,3-dicarboxylate (1105663-94-2) continues to demonstrate versatility across multiple pharmaceutical research domains. Its structural features enable diverse modifications that address contemporary challenges in drug discovery, from protein degradation to molecular imaging. Ongoing research is expected to further expand its applications, particularly in targeted therapies and personalized medicine approaches.

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