281652-10-6 | tert-butyl 4,4-difluoropiperidine-1-carboxylate

CAS:281652-10-6 | tert-butyl 4,4-difluoropiperidine-1-carboxylate,Description

Tert-butyl 4,4-difluoropiperidine-1-carboxylate is a chemical compound with the molecular formula C10H17F2NO2. It is a derivative of piperidine, a heterocyclic organic compound. The compound is characterized by the presence of a piperidine ring, which is a six-membered ring with one nitrogen atom and five carbon atoms.

Molecular Structure Analysis

The molecular structure of Tert-butyl 4,4-difluoropiperidine-1-carboxylate can be analyzed using various spectroscopic techniques. For instance, 1H NMR, 13C NMR, MS, and FT-IR techniques can be used to characterize the compound. Additionally, its single crystal can be evaluated using X-ray diffraction (XRD).

Physical And Chemical Properties Analysis

Tert-butyl 4,4-difluoropiperidine-1-carboxylate has a molecular weight of 221.24 g/mol. It has a computed XLogP3-AA value of 2.3, indicating its lipophilicity. The compound has no hydrogen bond donors and four hydrogen bond acceptors. Its topological polar surface area is 29.5 Ų. The compound has a rotatable bond count of 2.

Scientific Research Applications

Synthesis and Chemical Transformations

• Tert-butyl 4,4-difluoropiperidine-1-carboxylate derivatives are used in stereoselective syntheses of substituted compounds, such as tert-butyl 3-allyl-4-hydroxypiperidine-1-carboxylates. These syntheses involve reactions with L-selectride and Mitsunobu reaction for isomer formation (Boev et al., 2015).
• This compound serves as an intermediate in the synthesis of protein tyrosine kinase Jak3 inhibitors, with a synthesis process involving a series of steps like SN2 substitution and borohydride reduction (Chen Xin-zhi, 2011).
• Tert-butyl 4-oxopiperidine-1-carboxylate dimethylhydrazone is involved in the formation of N-Boc piperidine derivatives fused with oxygen heterocycles, showing high stereoselectivity in cyclization (Moskalenko & Boev, 2014).

Pharmaceutical and Medicinal Chemistry

• Tert-butyl 4-oxopiperidine-1-carboxylate derivatives are used as synthons for the preparation of diverse piperidine derivatives, which have potential applications in pharmaceutical research (Moskalenko & Boev, 2014).
• Tert-butyl 4-formyl-3, 6-dihydropyridine-1(2H)-carboxylate, a related compound, is an important intermediate for small molecule anticancer drugs. Its synthesis involves nucleophilic substitution and oxidation reactions (Zhang et al., 2018).

Molecular and Structural Chemistry

• X-ray studies of tert-butyl (6S)-4-hydroxy-6-isobutyl-2-oxopiperidine-1-carboxylate have revealed molecular packing driven by strong O-H...O=C hydrogen bonds, important for understanding molecular interactions in crystal structures (Didierjean et al., 2004).
• Tert-butylcarbonyl 1,2,3,6-tetrahydro-4-[(trifluoromethyl)sulfonyloxy]pyridine-1-carboxylate, a related compound, has been studied for its potential in palladium-catalyzed coupling reactions, contributing to advancements in molecular synthesis techniques (Wustrow & Wise, 1991).

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