52937-71-0

Basic information

• Product Name: 5-(1-Methylbutyl)-5-(2-propenyl)-1,3-bis(trimethylsilyl)-2,4,6(1H,3H,5H)-pyrimidinetrione
• Synonyms: 5-(1-Methylbutyl)-5-(2-propenyl)-1,3-bis(trimethylsilyl)-2,4,6(1H,3H,5H)-pyrimidinetrione
• CAS NO: 52937-71-0
• Molecular Formula: C18H34N2O3Si2
• Molecular Weight: 382.65
• Mol File: 52937-71-0.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-(1-Methylbutyl)-5-(2-propenyl)-1,3-bis(trimethylsilyl)-2,4,6(1H,3H,5H)-pyrimidinetrione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(1-Methylbutyl)-5-(2-propenyl)-1,3-bis(trimethylsilyl)-2,4,6(1H,3H,5H)-pyrimidinetrione(52937-71-0)
• EPA Substance Registry System: 5-(1-Methylbutyl)-5-(2-propenyl)-1,3-bis(trimethylsilyl)-2,4,6(1H,3H,5H)-pyrimidinetrione(52937-71-0)

Safety Data

• Hazardous Substances Data: 52937-71-0(Hazardous Substances Data)

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 76-73-3 5-Allyl-5-(1-methyl-butyl)-barbitursaeure; Secobarbital 

Relevant articles and documents

N-Glucosylation of 5,5-Disubstituted Barbiturates by Mouse Liver Microsomes

The structure-substrate relationships of the imide N-glucosylation pathway were investigated in mouse liver microsomes by testing 5,5-disubstituted barbiturates (amobarbital, aprobarbital, barbital, barbituric acid, butabarbital, butalbital, pentobarbital, and secobarbital) for their ability to inhibit phenobarbital N-glucosylation. After inhibition of phenobarbital N-glucosylation was demonstrated, evidence for formation of new barbiturate N-glucosides was obtained. Aprobarbital and secobarbital N-glucosides were synthesized to verify their formation by mouse liver microsomes. The apparent Km and Vmax values for formation of amobarbital, aprobarbital, (1'R,S)-secobarbital, (1'R,S)-, (1'R)-, and (1'S)-pentobarbital N-glucoside conjugates were obtained. Increasingly lipophilic barbiturates exhibited increasing inhibition of phenobarbital N-glucosylation and this was associated with a lower Km for N-glucosylation of the respective barbiturate. Changing the C-5 ethyl to a C-5 allyl had no effect on the efficiency of the conjugation reaction (Vmax/Km). Product enantioselectivity was observed for all of the barbiturate N-glucosides for which separation of the diastereomers was achieved. Approximately a two-fold substrate enantioselectivity for N-glucosylation was observed for (R)-pentobarbital(S)-pentobarbital and the product enantioselectivity was different for each isomer. The formation of N-glucoside conjugates appears to be a general enzymatic pathway for the biotransformation of 5,5-disubstituted barbiturates in mouse liver microsomes.