(S)-(-)-4-Isopropyl-5,5-diphenyl-2-oxazolidinone
[CAS# 184346-45-0]

Identification

• Classification: Organic raw materials >> Ketone compound
• Name: (S)-(-)-4-Isopropyl-5,5-diphenyl-2-oxazolidinone
• Synonyms: (4S)-5,5-diphenyl-4-propan-2-yl-1,3-oxazolidin-2-one
• Molecular Formula: C₁₈H₁₉NO₂
• Molecular Weight: 281.35
• CAS Registry Number: 184346-45-0
• SMILES: CC(C)[C@H]1C(OC(=O)N1)(C2=CC=CC=C2)C3=CC=CC=C3

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Melting point: 252-255 °C (Expl.)
• Index of Refraction: 1.563, Calc.^*
• Boiling Point: 475.7±45.0 °C (760 mmHg), Calc.^*
• Flash Point: 241.5±28.7 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501

Discovery and Applications

(S)-(-)-4-Isopropyl-5,5-diphenyl-2-oxazolidinone is a chiral oxazolidinone compound that has garnered attention in the fields of medicinal chemistry and organic synthesis due to its versatile structural properties and potential applications. The oxazolidinone core is a heterocyclic structure, which is often used as a scaffold in the development of biologically active compounds. The presence of the isopropyl and diphenyl groups at specific positions on the oxazolidinone ring confers unique steric and electronic properties, making this compound an interesting subject for research in asymmetric synthesis and catalysis.

The discovery of (S)-(-)-4-isopropyl-5,5-diphenyl-2-oxazolidinone emerged from ongoing efforts to develop chiral auxiliaries and catalysts for asymmetric reactions. Oxazolidinones like this compound are commonly used as chiral ligands in catalysis because of their ability to induce chirality in reactions that would otherwise produce racemic mixtures. The synthesis of chiral compounds with high enantiomeric purity is a critical goal in pharmaceutical chemistry, as many bioactive molecules require a specific enantiomer to be effective. The stereochemistry of (S)-(-)-4-isopropyl-5,5-diphenyl-2-oxazolidinone is particularly useful because it can be employed in asymmetric transformations to produce chiral molecules with high precision.

One of the primary applications of (S)-(-)-4-isopropyl-5,5-diphenyl-2-oxazolidinone is in asymmetric synthesis, where it serves as a chiral auxiliary or ligand in various catalytic processes. In particular, it is used in reactions such as asymmetric reduction, alkylation, and cyclization, which are vital for the synthesis of complex organic molecules. The ability of this compound to control the stereochemistry of the product has made it an important tool in the preparation of pharmaceuticals, agrochemicals, and other fine chemicals. The diphenyl and isopropyl groups on the oxazolidinone ring influence the electronic environment and steric hindrance around the reaction site, which helps to direct the formation of the desired enantiomer.

In addition to its use in catalysis, (S)-(-)-4-isopropyl-5,5-diphenyl-2-oxazolidinone has potential applications in the development of new drugs. The compound's structure is similar to known classes of biologically active molecules, which has led to its exploration as a lead compound for the development of novel therapeutics. The oxazolidinone framework is of particular interest in drug discovery because it can be modified to interact with a variety of biological targets, including enzymes and receptors. For example, oxazolidinones are known to have antibacterial properties, and derivatives of this class of compounds are under investigation as potential antibiotics.

Furthermore, the versatility of (S)-(-)-4-isopropyl-5,5-diphenyl-2-oxazolidinone extends to its use in materials science. The compound's chiral properties and ability to form stable complexes with metal ions make it useful in the design of chiral materials, which can be applied in fields such as optoelectronics and sensors. Chiral materials are important in the development of advanced technologies that rely on the manipulation of light, such as circularly polarized light devices, and in the fabrication of sensitive detection systems that exploit chiral recognition.

In conclusion, (S)-(-)-4-isopropyl-5,5-diphenyl-2-oxazolidinone is a valuable compound with diverse applications in asymmetric synthesis, drug development, and materials science. Its ability to act as a chiral ligand in catalytic processes, coupled with its potential for creating new bioactive molecules and materials, ensures its continued relevance in chemical research and industrial applications.

References

2012. A Concise Asymmetric Synthesis of (-)-Virolin, (-)-Surinamensin, (-)-Raphidecursinol B and (-)-Polysphorin. Synlett.
DOI: 10.1055/s-0031-1290678

2002. Crystal Structures- AManifesto for the Superiority of the Valine-Derived 5,5-Diphenyloxazolidinone as an Auxiliary in Enantioselective Organic Synthesis. Helvetica Chimica Acta.
DOI: 10.1002/1522-2675(200206)85:6<1546::aid-hlca1546>3.0.co;2-2

2002. CCDC 190429: Experimental Crystal Structure Determination.
DOI: 10.5517/cc6d4wl