• 1. Dissolved oxygen sensor based on fluorescence quenching of oxygen-sensitive ruthenium complexes immobilized in sol–gel-derived porous silica coatings
  Analyst, 1996,121, 785-788
• 2. Excimer formation effects and trap-assisted charge recombination loss channels in organic solar cells of perylene diimide dimer acceptors?
  Min Kim,Jae-Joon Lee,Tengling Ye,Panagiotis E. Keivanidis,Kilwon Cho J. Mater. Chem. C, 2020,8, 1686-1696
• 3. Excitation dependent bidirectional electron transfer in phthalocyanine-functionalised MoS2 nanosheets?
  Christopher J. Harrison,Kyle J. Berean,Enrico Della Gaspera,Jian Zhen Ou,Richard B. Kaner,Kourosh Kalantar-zadeh,Torben Daeneke Nanoscale, 2016,8, 16276-16283
• 4. Ester-mediated peptide formation promoted by deep eutectic solvents: a facile pathway to proto-peptides?
  Chen-Yu Chien,Sheng-Sheng Yu Chem. Commun., 2020,56, 11949-11952
• 5. Excimer emission and magnetoluminescence of radical-based zinc(ii) complexes doped in host crystals?
  Shojiro Kimura,Tetsuro Kusamoto Chem. Commun., 2020,56, 11195-11198

Introduction to Tert-butyl (2S)-2-cyanopiperidine-1-carboxylate (CAS No. 242459-44-5)

Tert-butyl (2S)-2-cyanopiperidine-1-carboxylate, with the chemical formula C₁₁H₁₄N₂O₂, is a significant compound in the field of pharmaceutical chemistry and medicinal research. This compound, identified by its CAS number 242459-44-5, has garnered attention due to its unique structural properties and potential applications in drug development. The presence of a tertiary butyl group and a chiral center at the 2-position of the piperidine ring contributes to its complex behavior and makes it a subject of interest for synthetic chemists and pharmacologists.

The tert-butyl (2S)-2-cyanopiperidine-1-carboxylate structure is characterized by a piperidine core, which is a six-membered heterocyclic amine containing one nitrogen atom. This nitrogen atom is crucial for the compound's reactivity and biological activity. The (2S) configuration indicates the stereochemical arrangement of the chiral center, which plays a pivotal role in determining the compound's pharmacological properties. The cyanopiperidine moiety introduces a cyano group at the 2-position, enhancing the compound's potential as a building block for more complex molecules.

In recent years, there has been growing interest in piperidine derivatives due to their diverse biological activities. Piperidine-based compounds have shown promise in various therapeutic areas, including central nervous system (CNS) disorders, infectious diseases, and cancer. The tert-butyl (2S)-2-cyanopiperidine-1-carboxylate is no exception, and its unique structure has led to several innovative applications in medicinal chemistry.

One of the most compelling aspects of tert-butyl (2S)-2-cyanopiperidine-1-carboxylate is its role as a key intermediate in the synthesis of more complex pharmacophores. The tert-butyl group provides steric hindrance, which can influence the binding affinity of the compound to biological targets. Additionally, the chiral center at the 2-position allows for the creation of enantiomerically pure compounds, which are often required for optimal pharmacological activity. These features make tert-butyl (2S)-2-cyanopiperidine-1-carboxylate an invaluable tool for drug discovery and development.

Recent studies have highlighted the potential of tert-butyl (2S)-2-cyanopiperidine-1-carboxylate in the development of novel therapeutics. For instance, researchers have explored its use as a precursor in the synthesis of kinase inhibitors, which are crucial for treating various types of cancer. The cyanopiperidine moiety has been shown to interact effectively with ATP-binding sites on kinases, leading to potent inhibition of their activity. This has opened up new avenues for developing targeted cancer therapies.

The stereochemistry of tert-butyl (2S)-2-cyanopiperidine-1-carboxylate has also been investigated for its impact on biological activity. Studies have demonstrated that enantiomeric purity is essential for achieving optimal therapeutic effects. The (S) configuration at the 2-position has been found to enhance binding affinity and reduce off-target effects compared to its (R) counterpart. This underscores the importance of chirality in drug design and highlights why tert-butyl (2S)-2-cyanopiperidine-1-carboxylate is a valuable asset in medicinal chemistry.

In addition to its applications in oncology, tert-butyl (2S)-2-cyanopiperidine-1-carboxylate has shown promise in other therapeutic areas. For example, it has been used as a scaffold for developing antiviral agents. The piperidine core and cyanopiperidine moiety have been found to interact with viral proteases and enzymes, inhibiting their function and thereby reducing viral replication. This has significant implications for treating infectious diseases caused by viruses such as HIV and hepatitis C.

The synthesis of tert-butyl (2S)-2-cyanopiperidine-1-carboxylate has also been optimized to improve yield and scalability. Advanced synthetic methodologies have been employed to achieve high enantiomeric purity while maintaining cost-effectiveness. These advancements have made it possible to produce larger quantities of the compound for both research and commercial purposes.

The future prospects of tert-butyl (2S)-2-cyanopiperidine-1-carboxylate are promising, with ongoing research exploring new applications and improving existing ones. As our understanding of biological targets and disease mechanisms continues to evolve, compounds like this will play an increasingly important role in drug development. The unique structural features of tert-butyl (2S)-2-cyanopiperidine-1-carboxylate, combined with its versatility as a synthetic intermediate, make it a cornerstone in modern medicinal chemistry.

• 153749-89-4(tert-Butyl 2-cyanopiperidine-1-carboxylate)
• 228244-04-0(tert-butyl (2S)-2-cyanopyrrolidine-1-carboxylate)
• 228244-20-0(tert-butyl (2R)-2-cyanopyrrolidine-1-carboxylate)
• 849928-27-4(tert-butyl 4-cyano-4-(dimethylamino)piperidine-1-carboxylate)
• 144688-70-0(Tert-Butyl 2-cyanopyrrolidine-1-carboxylate)
• 1224923-48-1(tert-Butyl 4-((cyanomethyl)amino)piperidine-1-carboxylate)
• 361442-57-1(2-Azabicyclo[3.1.0]hexane-2-carboxylic acid, 3-cyano-,1,1-dimethylethyl ester, (1S,3S,5S)-)
• 940000-26-0(tert-butyl (2R)-2-cyanopiperidine-1-carboxylate)
• 866396-74-9((2R,5S)-tert-butyl 2,5-dicyanopyrrolidine-1-carboxylate)
• 724445-95-8(Carbamic acid,N-(1-cyano-5-hydroxypentyl)-N-methyl-, 1,1-dimethylethyl ester)