317360-04-6 | tert-butyl 4-(2-ethoxy-2-oxoethyl)-3-fluoropiperidine-1-carboxyl

CAS:317360-04-6 | tert-butyl 4-(2-ethoxy-2-oxoethyl)-3-fluoropiperidine-1-carboxyl,Description

The compound "Tert-butyl 4-(2-ethoxy-2-oxoethyl)-3-fluoropiperidine-1-carboxylate" is a fluorinated piperidine derivative. Fluorinated compounds are of significant interest in various fields, including drug discovery, due to the unique properties imparted by the incorporation of fluorine atoms into molecules. The presence of tert-butyl and fluoropiperidine groups suggests potential applications in medicinal chemistry and the synthesis of complex organic molecules.

Synthesis Analysis

The synthesis of related fluorinated piperidine derivatives has been explored in several studies. For instance, the synthesis of tert-butyl 4-methyl-3-oxopiperidine-1-carboxylate, an intermediate in the synthesis of protein tyrosine kinase inhibitors, has been reported with an efficient approach starting from 4-methylpyridinium and proceeding through several steps including SN2 substitution, borohydride reduction, oxidation, and debenzylation to achieve the target product. Similarly, the synthesis of tert-butyl 4-(5-(3-fluorophenyl)-1,2,4-oxadiazol-3-yl)piperazine-1-carboxylate involved a condensation reaction between carbamimide and 3-fluorobenzoic acid. These methods highlight the multi-step nature of synthesizing such compounds, which often require careful selection of reagents and conditions to achieve the desired product.

Molecular Structure Analysis

X-ray diffraction studies have been used to determine the molecular structure of related compounds. For example, the molecular structure of tert-butyl 4-(2-tert-butoxy-2-oxoethyl)piperazine-1-carboxylate was elucidated using X-ray crystallography, revealing typical bond lengths and angles for a piperazine-carboxylate. X-ray studies have also been conducted on tert-butyl (6S)-4-hydroxy-6-isobutyl-2-oxo-1,2,5,6-tetrahydropyridine-1-carboxylate, providing insights into the orientation of side chains and the configuration of hydroxylated lactams. These studies are crucial for understanding the three-dimensional arrangement of atoms in the molecule, which can influence its reactivity and interaction with biological targets.

Chemical Reactions Analysis

The reactivity of fluorinated piperidine derivatives has been explored in various contexts. For instance, 4-tert-butyl-2,6-dimethylphenylsulfur trifluoride has been used as a deoxofluorinating agent, capable of converting various functional groups to fluorinated analogs with high yields and stereoselectivity. The antimycobacterial activities of novel fluorinated naphthyridine derivatives have also been studied, with some compounds showing potent activity against Mycobacterium tuberculosis. These studies demonstrate the diverse fluorination capabilities and potential applications of fluorinated piperidine derivatives in medicinal chemistry.

Physical and Chemical Properties Analysis

The physical and chemical properties of fluorinated piperidine derivatives are influenced by the presence of fluorine atoms and the specific substituents on the piperidine ring. For example, the thermal stability and resistance to aqueous hydrolysis of phenylsulfur trifluorides have been investigated, with some derivatives showing high stability and utility as fluorinating agents. The crystallization behavior and intermolecular interactions, such as hydrogen bonding and π-π stacking, have been characterized for compounds like tert-butyl 4-(5-(3-fluorophenyl)-1,2,4-oxadiazol-3-yl)piperazine-1-carboxylate. These properties are essential for understanding the behavior of these compounds under different conditions and their suitability for various applications.

Scientific Research Applications

Synthesis and Characterization

A derivative of N-Boc piperazine, tert-butyl 4-(2-ethoxy-2-oxoethyl)-piperazine-1-carboxylate, has been synthesized and characterized, indicating the compound's utility in forming bases for further chemical modifications and studies. This process involves FT-IR, 1H & 13C NMR, and LCMS spectroscopic studies, alongside single crystal X-ray diffraction analysis, highlighting its role in understanding molecular structures and interactions (Kulkarni et al., 2016).

Biological Evaluation

The same study also explored the antibacterial and antifungal activities of tert-butyl 4-(2-ethoxy-2-oxoethyl)-piperazine-1-carboxylate derivatives. These compounds showed moderate activity against several microorganisms, pointing to their potential in developing new antimicrobial agents (Kulkarni et al., 2016).

Molecular Structure Insights

Research on related compounds, such as tert-butyl 4-(2-tert-butoxy-2-oxoethyl)piperazine-1-carboxylate, provides valuable information on their molecular and crystal structure. Such insights are crucial for the design of molecules with desired physical and chemical properties, enabling targeted applications in material science and drug development (Mamat, Flemming, & Köckerling, 2012).

Intermediate in Synthesis Processes

Compounds structurally related to the tert-butyl 4-(2-ethoxy-2-oxoethyl)-3-fluoropiperidine-1-carboxylate serve as intermediates in the synthesis of biologically active compounds, such as omisertinib (AZD9291), highlighting their importance in pharmaceutical research and development (Zhao et al., 2017).

Safety And Hazards

The safety information for this compound indicates that it should be handled with care. Users are advised to avoid breathing its dust/fume/gas/mist/vapors/spray and to use it only outdoors or in a well-ventilated area. It’s also recommended to keep it away from heat/sparks/open flames/hot surfaces.

Future Directions

As a derivative of N-Boc piperazine, this compound serves as a useful building block/intermediate in the synthesis of several novel organic compounds such as amides, sulphonamides, Mannich bases, Schiff’s bases, thiazolidinones, azetidinones, and imidazolinones. These derived compounds have shown a wide spectrum of biological activities, suggesting potential future directions for research and application.

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