27534-88-9 Usage
Description
(5S)-5-phenyl-2,4-imidazolinedione, also known as R-(-)-GMPC, is a chiral chemical compound with the molecular formula C9H8N2O2. It features a phenyl group and an imidazolidine ring in its structure, which contributes to its unique properties and potential applications.
Uses
Used in Organic Synthesis:
(5S)-5-phenyl-2,4-imidazolinedione is used as a reagent in organic synthesis for its ability to participate in various chemical reactions, facilitating the creation of new compounds and molecules.
Used as a Chiral Auxiliary in Asymmetric Synthesis:
In the field of asymmetric synthesis, (5S)-5-phenyl-2,4-imidazolinedione is utilized as a chiral auxiliary. Its specific stereochemistry aids in the selective formation of desired enantiomers, which is crucial in the production of biologically active compounds.
Used in Coordination Chemistry:
(5S)-5-phenyl-2,4-imidazolinedione has the potential to form coordination complexes with metal ions. This property makes it a valuable compound in coordination chemistry, where it can be used to study and develop new metal complexes with potential applications in catalysis, materials science, and other areas.
Used in Pharmaceutical Applications:
Due to its structure and properties, (5S)-5-phenyl-2,4-imidazolinedione may have biological activity and has been investigated for its potential pharmacological effects. It could be used as a starting point for the development of new drugs or as a component in the synthesis of pharmaceutical compounds.
Used in Chemical Research:
The unique structure and properties of (5S)-5-phenyl-2,4-imidazolinedione make it an interesting subject for chemical research. It can be used to study various aspects of chemistry, such as reaction mechanisms, stereochemistry, and the development of new synthetic methods.
Check Digit Verification of cas no
The CAS Registry Mumber 27534-88-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,7,5,3 and 4 respectively; the second part has 2 digits, 8 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 27534-88:
(7*2)+(6*7)+(5*5)+(4*3)+(3*4)+(2*8)+(1*8)=129
129 % 10 = 9
So 27534-88-9 is a valid CAS Registry Number.
27534-88-9Relevant articles and documents
Dibromohydantoins as halogen bond (XB) donors: a route toward the introduction of chirality in halogen bonded systems
Nicolas, Irène,Jeannin, Olivier,Pichon, Delphine,Fourmigué, Marc
, p. 9325 - 9333 (2016)
N,N′-Dibromohydantoins, known as electrophilic bromination reagents, are successfully used here as halogen bond (XB) donors, as demonstrated in their crystalline adducts with para-substituted pyridines acting as halogen bond acceptors. 1:1 adducts of the achiral 5,5-dimethyl-N,N′-dibromohydantoin (DBH) are crystallized with methylisonicotinate, 4-trifluoromethylpyridine and 4-cyanopyridine, while both nitrogen atoms of pyrazine are engaged in halogen bonding in the 2:1 adduct (DBH)2·(pyrazine). A strengthening of the XB interaction between the imidic N-Br group of DBH and the pyridinic nitrogen atom is observed with the more electron rich pyridines in the order Py-CO2Me > Py-CF3 > Py-CN > pyrazine. Chiral hydantoins and their N,N′-dibromo derivatives are obtained in good yields from different amino acids (phenylglycine, phenylalanine, valine and leucine). The ability of such enantiopure N-iodoimide derivatives to act as halogen-bond donors is demonstrated in the 1:1 methylisonicotinate adduct with (S)-5-isobutyl-N,N′-dibromohydantoin.
Mechanochemical preparation of hydantoins from amino esters: Application to the synthesis of the antiepileptic drug phenytoin
Konnert, Laure,Reneaud, Benjamin,De Figueiredo, Renata Marcia,Campagne, Jean-Marc,Lamaty, Frdric,Martinez, Jean,Colacino, Evelina
, p. 10132 - 10142 (2015/02/19)
The eco-friendly preparation of 5- and 5,5-disubstituted hydantoins from various amino ester hydrochlorides and potassium cyanate in a planetary ball-mill is described. The one-pot/two-step protocol consisted in the formation of ureido ester intermediates, followed by a base-catalyzed cyclization to hydantoins. This easy-handling mechanochemical methodology was applied to a large variety of α- and β-amino esters, in smooth conditions, leading to hydantoins in good yields and with no need of purification steps. As an example, the methodology was applied to the "green" synthesis of the antiepileptic drug Phenytoin, with no use of any harmful organic solvent.
