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Specifications of 3-(Methoxycarbonyl)bicyclo1.1.1pentane-1-carboxylic acid丨CAS 83249-10-9
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Appearance |
Off-white or white powder |
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Purity |
99% min |
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Identification |
The principal peak in the chromatogram obtained with the test solution is similar in retention time to the principal peak in the chromatogram obtained with reference solution |
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Maximum single impurity |
0.5% max |
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Moisture |
0.5% max |
Applications
1. Pharmaceutical and Medicinal Chemistry
3-(Methoxycarbonyl)bicyclo1.1.1pentane-1-carboxylic acid丨CAS 83249-10-9 is used as a building block or intermediate in the synthesis of novel drug candidates due to its unique bicyclic structure which imparts rigidity and metabolic stability.
The bicyclo[1.1.1]pentane scaffold is increasingly recognized as a bioisostere of phenyl rings, making this compound valuable in drug design to improve pharmacokinetic and pharmacodynamic profiles.
Incorporated into molecules to enhance binding affinity and selectivity by restricting conformational flexibility.
2. Organic Synthesis
Employed in synthetic chemistry as a versatile intermediate to introduce the bicyclo[1.1.1]pentane motif into complex molecules.
Reactivity of the carboxylic acid and ester groups allows for further functionalization, enabling diverse chemical transformations.
3. Material Science
Potentially used in the design of novel polymers and materials where the rigid bicyclic core can enhance mechanical properties and stability.
4. Chemical Research
Utilized in structure–activity relationship (SAR) studies and method development for exploring the effects of rigid bioisosteres in small molecule libraries.
Benefits
1. Rigid Bicyclic Core for Structural Stability
The bicyclo[1.1.1]pentane structure confers high three-dimensional rigidity, useful in molecular scaffolds where shape and orientation critically affect biological activity.
2. Bioisosteric Replacement
Serves as a phenyl ring substitute to improve drug-like properties such as:
Increased metabolic stability
Improved solubility
Reduced off-target interactions
3. Functional Group Versatility
Contains carboxylic acid and ester groups which allow for further derivatization, enabling incorporation into a wide range of chemical entities.
4. Improved Pharmacokinetic Profiles
Molecules incorporating this scaffold often show better bioavailability and reduced toxicity, making it attractive in medicinal chemistry.
Conclusion
3-(Methoxycarbonyl)bicyclo1.1.1pentane-1-carboxylic acid丨CAS 83249-10-9 is an important rigid bicyclic intermediate widely used in medicinal chemistry and organic synthesis. Its unique bicyclo[1.1.1]pentane core offers a valuable bioisosteric alternative to aromatic rings, contributing to the development of drugs with enhanced metabolic stability and efficacy. Its versatility in chemical modification and incorporation into diverse molecules makes it a critical tool for innovation in pharmaceuticals and material science.
