41807-35-6

Usage

Uses

Used in Pharmaceutical Research:
2,4-Imidazolidinedione, 5-phenyl-, (5R)is used as a chiral building block for the synthesis of pharmaceuticals, contributing to the development of new drugs and biologically active compounds. Its specific stereochemistry allows for the creation of enantiomerically pure compounds, which is crucial for ensuring the desired biological activity and minimizing potential side effects.
Used in Organic Synthesis:
In the field of organic synthesis, 2,4-Imidazolidinedione, 5-phenyl-, (5R)serves as a versatile intermediate for the preparation of a wide range of organic compounds. Its reactivity and structural features make it a valuable component in the synthesis of complex molecules and advanced materials.
Used in Drug Development:
2,4-Imidazolidinedione, 5-phenyl-, (5R)is utilized in drug development for its potential applications in creating new therapeutic agents. Its unique properties and chiral nature facilitate the design and synthesis of innovative drugs with improved efficacy and selectivity.
Used in Chemical Research:
In the realm of chemical research, 2,4-Imidazolidinedione, 5-phenyl-, (5R)is employed to study the fundamental aspects of chemical reactions and mechanisms. Its optical activity and structural features provide insights into stereoselective synthesis and the influence of stereochemistry on molecular properties and reactivity.

Upstream product

• 590-28-3 potassium cyanate 
• 875-74-1 (R)-phenylglycine 
• 27534-88-9 (5S)-5-phenyl-2,4-imidazolinedione 
• 6489-76-5 D-(-)-N-carbamoyl phenyl glycine 

Relevant academic research and scientific papers

Kinetics and mechanisms of racemization: 5-Substituted hydantoins (= imidazolidine-2,4-diones) as models of chiral drugs

A chiral center in a drug molecule increases the complexity of synthetic, metabolic, pharmacological, and clinical studies, an additional problem being a possible lack of configurational stability. Here, we report detailed kinetic and mechanistic studies on the deuteration and racemization of seven 5-monosubstituted hydantoins ( = imidazolidine-2,4-diones) used as model compounds. Using 1H-NMR and chiral RP-HPLC, rates of reaction and thermodynamic parameters of activation were determined for the reactions of deuteration and racemization. Energies of deprotonation were obtained by molecular-orbital calculations performed at the AMI level. It is demonstrated that the deuteration and racemization of 5-monosubstituted hydantoins follow general-base catalysis. The identical (within experimental errors) activation energies of deuteration and racemization indicate that the two reactions share a common reaction mechanism. The fact that the pseudo-first-order rate constants of deuteration are about half of those of racemization suggests that deuteration occurs with inversion of configuration. Very large differences in reaction rates were observed between the seven compounds, indicating the marked influence of substituents on chiral stability. These results, together with the small isotope effects observed, and the comparison between experimental activation energies and calculated energies of deprotonation, suggest a S(E)2 push-pull mechanism for the racemization of 5-monosubstituted hydantoins.

Cyclization and Molecular Rearrangement Under Micellar and Microemulsion Conditions

Reaction procedures for Beckmann rearrangement and cyclization can be improved substantially if carried out under micellar/microemulsion conditions.This mode of operation allows the use of dilute acids as against the conventional highly acidic medium with ease of product recovery and yield.Experimental results for a case example of D-(-)-N-carbamoyl phenyl glycine to phenyl hydantoin are presented and analysed.

Footprint catalysis. IX. Molecular footprint catalytic cavities imprinted with chiral hydantoins; enantioselective hydantoinase mimics

Imprinting using chiral 5-phenyhydantoins ((5R)- and (5S)-5-pheny-2,4-imidazolinedione) as templates could mark chiral molecular footprint-like cavities on a silica (alumina) gel surface. These cavities displayed evident enantioselective catalyses in reac