(R)-(+)-4-Isopropyl-5,5-diphenyl-2-oxazolidinone
[CAS# 191090-32-1]

Identification

• Classification: Organic raw materials >> Ketone compound
• Name: (R)-(+)-4-Isopropyl-5,5-diphenyl-2-oxazolidinone
• Synonyms: (4R)-5,5-diphenyl-4-propan-2-yl-1,3-oxazolidin-2-one
• Molecular Formula: C₁₈H₁₉NO₂
• Molecular Weight: 281.35
• CAS Registry Number: 191090-32-1
• 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

(R)-(+)-4-Isopropyl-5,5-diphenyl-2-oxazolidinone is a chiral organic compound that has garnered attention due to its potential applications in asymmetric synthesis and medicinal chemistry. The molecule belongs to the class of oxazolidinones, which are widely studied for their versatility in catalysis and drug design. This particular compound features a distinctive structure with an isopropyl group attached to the 4-position of the oxazolidinone ring, as well as two phenyl groups at the 5-position. Its chiral nature, indicated by the (R)-configuration, plays a crucial role in its ability to induce enantioselectivity in chemical reactions, making it a useful tool in various synthetic processes.

The discovery of (R)-(+)-4-isopropyl-5,5-diphenyl-2-oxazolidinone was part of the ongoing effort to develop new chiral auxiliaries and ligands for asymmetric reactions. Oxazolidinones have long been recognized for their ability to coordinate with metal catalysts, enabling the efficient production of chiral compounds. The introduction of bulky substituents such as the isopropyl and diphenyl groups enhances the steric and electronic properties of the molecule, facilitating its use in a range of stereoselective reactions. These characteristics make it an attractive candidate for applications in the synthesis of complex, optically active molecules.

One of the primary applications of (R)-(+)-4-isopropyl-5,5-diphenyl-2-oxazolidinone is in asymmetric catalysis, particularly in the synthesis of chiral pharmaceuticals. The compound acts as a chiral ligand in metal-catalyzed reactions, where it helps control the stereochemistry of the products. This is especially important in the pharmaceutical industry, where the production of enantiomerically pure compounds is crucial for ensuring the efficacy and safety of drugs. The ability to selectively produce one enantiomer over the other can significantly impact the pharmacological properties of a drug, including its activity, side effects, and toxicity.

In addition to its role in catalysis, (R)-(+)-4-isopropyl-5,5-diphenyl-2-oxazolidinone has potential applications in the development of new materials. The unique combination of its chiral center and aromatic phenyl groups offers opportunities for the design of advanced materials with specific properties, such as optical activity or selective binding to certain substrates. These materials could be useful in areas such as sensors, optoelectronics, or even molecular recognition systems.

Furthermore, the compound’s structure and reactivity make it a valuable building block for the synthesis of more complex molecules. It can be used as a starting point for the creation of other chiral oxazolidinones or incorporated into larger molecular frameworks that have applications in drug design, where chirality is a critical factor. Research into the modification and functionalization of (R)-(+)-4-isopropyl-5,5-diphenyl-2-oxazolidinone continues to expand its potential uses, as scientists explore its ability to serve as a versatile intermediate in the synthesis of biologically active compounds.

The compound also plays a role in the development of new stereoselective processes that could be employed in green chemistry. Its ability to induce chirality with minimal waste and under mild conditions makes it an attractive candidate for sustainable chemistry practices. The use of such compounds in the synthesis of fine chemicals and pharmaceuticals could lead to more efficient and environmentally friendly processes.

In conclusion, (R)-(+)-4-isopropyl-5,5-diphenyl-2-oxazolidinone is a chiral compound with important applications in asymmetric synthesis, catalysis, and material science. Its ability to induce enantioselectivity in chemical reactions, combined with its utility as a building block for the synthesis of complex molecules, makes it a valuable tool in the development of new drugs and materials. Ongoing research into its properties and applications continues to expand its role in both academic and industrial chemistry.

References

2007. Base-Induced Lactonization. Science of Synthesis. https://science-of-synthesis.thieme.com/app/text/?id=SD-020-01379