3-[(tert-Butylsulfinyl)imino]oxetan
[CAS# 1158098-73-7]

Identification

• Classification: Organic raw materials >> Heterocyclic compound
• Name: 3-[(tert-Butylsulfinyl)imino]oxetan
• Synonyms: 2-Methyl-N-3-oxetanylidene-2-propanesulfinamide
• Molecular Formula: C₇H₁₃NO₂S
• Molecular Weight: 175.25
• CAS Registry Number: 1158098-73-7
• SMILES: CC(C)(C)S(=O)N=C1COC1

Properties

• Density: 1.25
• Boiling point: 302.8+-52.0 °C (760 mmHg)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

The discovery of 3-[(tert-butylsulfinyl)imino]oxetane stems from efforts to develop novel sulfenyl imine derivatives with enhanced reactivity and selectivity in organic synthesis. The compound was first synthesized in the early 2000s, combining oxetane chemistry and sulfenyl imine technology. The synthesis involves the reaction of oxetane ketone with tert-butylsulfinamide, followed by oxidation and cyclization to form the oxetane ring. The chemical structure of 3-[(tert-butylsulfinyl)imino]oxetane is characterized by: the four-membered oxetane ring is known for its high strain and reactivity, making it a useful building block for the synthesis of more complex structures; the tert-butylsulfinyl group stabilizes the imine functionality, improves solubility, and controls stereochemistry during reactions; and the imino (R=N−) group serves as a versatile site for nucleophilic and electrophilic additions, allowing the compound to participate in a variety of chemical transformations.

The main application of 3-[(tert-butylsulfinyl)imino]oxetane is in asymmetric synthesis. The compound acts as a chiral auxiliary, promoting the formation of enantiomerically pure products. Its chiral sulfinyl group directs the addition of nucleophiles or electrophiles, resulting in high selectivity for the formation of chiral centers. This property is essential for the synthesis of complex molecules with specific stereochemistry required for pharmaceutical applications.

The oxetane ring provides a strained, highly reactive moiety that can be used to build larger heterocyclic compounds. Through ring-opening reactions and further functionalization, 3-[(tert-butylsulfinyl)imino]oxetane can be transformed into a variety of heterocycles, including pyrrolidines, piperidines, and more complex fused ring systems. These heterocycles are the building blocks of many natural products and pharmaceuticals.

The imino group in 3-[(tert-butylsulfinyl)imino]oxetane is highly reactive toward nucleophiles, allowing a variety of nucleophiles to add to form new carbon-nitrogen bonds. This reactivity makes the compound useful in Mannich-type reactions, aza-Michael additions, and other nucleophilic addition reactions to form a variety of nitrogen-containing compounds.

In drug development, 3-[(tert-butylsulfinyl)imino]oxetane can be used as a starting material for the synthesis of bioactive molecules. Its ability to form chiral centers and complex heterocycles is valuable in creating new drug candidates with improved efficacy and selectivity.

The inherent stability of the oxetane ring gives 3-[(tert-butylsulfinyl)imino]oxetane-derived drug candidates excellent metabolic stability. Oxetane-containing drugs often exhibit resistance to metabolic degradation, resulting in extended half-lives and improved pharmacokinetic profiles.

The reactive imino group of this compound enables bioconjugation, the process of linking small molecules to biomolecules such as proteins, peptides, or nucleic acids. This application is important for creating targeted drug delivery systems, diagnostic agents, and therapeutic conjugates. Bioconjugates formed with 3-[(tert-butylsulfinyl)imino]oxetane exhibit enhanced specificity and functionality, aiding the development of personalized medicine and targeted therapies.

In industrial chemistry, 3-[(tert-butylsulfinyl)imino]oxetane is used to synthesize fine chemicals, agrochemicals, and specialty materials. The compound can act as a ligand or intermediate in catalytic cycles, forming stable complexes with metals and participating in catalytic transformations. In materials science, 3-[(tert-butylsulfinyl)imino]oxetane is used to make advanced materials with customized properties. Its addition to polymers or other materials can give them specific mechanical, chemical, or thermal properties.

References

2018. Nucleophilic Additions to Imines and Iminium Species. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-137-00029

2011. Gold-Catalyzed Stereoselective Synthesis of Azetidin-3-ones. Synfacts.
DOI: 10.1055/s-0030-1260395