Overview
Ethyl 3-oxo-4-phenylbutanoate (CAS 718-08-1) is a β-keto ester building block widely employed as a key intermediate in the synthesis of pharmaceutical agents targeting oncology, virology, and metabolic disorders. This molecule features a β-keto ester functionality adjacent to a phenyl ring, enabling diverse downstream transformations including alkylation, condensation, and cyclization reactions.
Patent Landscape
Patent literature reveals Ethyl 3-oxo-4-phenylbutanoate as a critical intermediate in drug discovery programs by major pharmaceutical companies including Bayer AG (3.5% of related patents), AstraZeneca (1.8%), Takeda (1.5%), and GlaxoSmithKline (1.4%). Key patent applications include:
KRas G12C Inhibitors (Mirati Therapeutics, US10647715B2)
Ethyl 3-oxo-4-phenylbutanoate serves as a synthetic intermediate for irreversible KRas G12C inhibitors targeting the switch II region. The β-keto ester moiety undergoes condensation reactions to construct the heterocyclic core essential for target engagement. This represents a major therapeutic application in non-small cell lung cancer (NSCLC) and colorectal cancer.
HIV-1 Reverse Transcriptase Inhibitors (Capital Medical University, CN101597263A; CN101016265A)
Two Chinese patents explicitly describe the use of Ethyl 3-oxo-4-phenylbutanoate as a starting material for S-DABO class HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs). The published synthesis route: Ethyl 3-oxo-4-phenylbutanoate (18 g) is reduced with activated Zn powder in anhydrous THF under HCl gas, yielding the target compound at 92.8% purity. The reaction involves carefully controlled conditions: Zn activation with 3N HCl, washing with anhydrous EtOH and Et₂O, followed by vacuum drying.
Hematopoietic Stem Cell Expansion (Université de Montréal, US10647718B2)
This patent utilizes ethyl 3-oxo-4-phenylbutanoate derivatives for expanding hematopoietic stem and progenitor cell populations, with applications in bone marrow transplantation and regenerative medicine.
Kinase Inhibitors (Novartis, US20130109682A1)
Novartis patents describe cyclic ether compounds incorporating the 3-oxo-4-phenylbutanoate scaffold as kinase inhibitors for the treatment of proliferative disorders.
PPAR Activators (SmithKline Beecham/GSK, US7449468B2)
The compound serves as an intermediate for hPPAR agonists used in treating dyslipidemia, Syndrome X, and related metabolic conditions.
Synthetic Utility
Ethyl 3-oxo-4-phenylbutanoate offers three primary reactive centers:
- C2 methylene group: Enables alkylation and condensation reactions to build heterocyclic systems
- β-Keto ester moiety: Participates in Knoevenagel condensations, Michael additions, and Dieckmann cyclizations
- Phenyl ring: Provides π-stacking interactions in target protein binding sites
Quality Specifications
| Parameter | Specification |
|---|---|
| CAS Number | 718-08-1 |
| Molecular Formula | C₁₂H₁₄O₃ |
| Molecular Weight | 206.24 g/mol |
| Appearance | Colorless to pale yellow liquid |
| Purity (HPLC) | ≥97.0% |
| Boiling Point | 285-290 °C |
| Density | 1.095 g/mL at 25 °C |
| Storage | 2-8 °C, protected from moisture |
Conclusion
Ethyl 3-oxo-4-phenylbutanoate (CAS 718-08-1) is a versatile β-keto ester intermediate validated across oncology, antiviral, and metabolic therapeutic programs. Its synthetic flexibility and established role in pharmaceutical manufacturing make it a valuable building block for medicinal chemistry and process R&D.
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