138522-39-1

Basic information

• Product Name: 2-Imidazolidinone, 4-(1-methylethyl)-1-phenyl-, (S)-
• CAS NO: 138522-39-1
• Molecular Formula: C12H16N2O
• Molecular Weight: 204.272
• Mol File: 138522-39-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2-Imidazolidinone, 4-(1-methylethyl)-1-phenyl-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Imidazolidinone, 4-(1-methylethyl)-1-phenyl-, (S)-(138522-39-1)
• EPA Substance Registry System: 2-Imidazolidinone, 4-(1-methylethyl)-1-phenyl-, (S)-(138522-39-1)

Safety Data

• Hazardous Substances Data: 138522-39-1(Hazardous Substances Data)

Upstream product

• 223600-52-0 1-((S)-1-hydroxymethyl-2-methyl-propyl)-3-phenyl-urea 
• 1110273-57-8 (S)-2-isopropyl-1-((2-nitrophenyl)sulfonyl)aziridine 
• 129473-55-8 (S)-2-amino-3-methyl-N-phenylbutanamide 
• 72-18-4 L-valine 
• 13734-41-3 t-Boc-L-valine 
• 1375257-35-4 (S)-3-[(S)-3-hydroxy-3-phenylpropanoyl]-4-isopropyl-1-phenylimidazolidin-2-one 
• 1375257-27-4 N-acetyl-(S)-4-isopropyl-1-phenylimidazolidine-2-one 
• 908253-01-0 (S)-N¹-phenyl-3-methylbutane-1,2-diamine 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 126787-26-6 ((S)-2-methyl-1-phenylcarbamoylpropyl)carbamic acid tert-butyl ester 
• 103-71-9 phenyl isocyanate 
• 2026-48-4 (S)-valinol 

Downstream Products

• 195198-27-7 (S)-4-isopropyl-1-phenyl-3-propionyl-imidazolidin-2-one 
• 158724-94-8 (S)-3-(2-Benzyloxy-acetyl)-4-isopropyl-1-phenyl-imidazolidin-2-one 
• 1375257-27-4 N-acetyl-(S)-4-isopropyl-1-phenylimidazolidine-2-one 
• 1375257-35-4 (S)-3-[(S)-3-hydroxy-3-phenylpropanoyl]-4-isopropyl-1-phenylimidazolidin-2-one 
• 868944-62-1 (S)-3-((R)-2-Benzyloxy-3-phenyl-propionyl)-4-isopropyl-1-phenyl-imidazolidin-2-one 
• 868944-63-2 (S)-3-((R)-2-Benzyloxy-pent-4-enoyl)-4-isopropyl-1-phenyl-imidazolidin-2-one 

Relevant articles and documents

Conformationally Programmable Chiral Foldamers with Compact and Extended Domains Controlled by Monomer Structure

Foldamers are an important class of abiotic macromolecules, with potential therapeutic applications in the disruption of protein–protein interactions. The majority adopt a single conformational motif such as a helix. A class of foldamer is now introduced where the choice of heterocycle within each monomer, coupled with a strong conformation-determining dipole repulsion effect, allows both helical and extended conformations to be selected. Combining these monomers into hetero-oligomers enables highly controlled exploration of conformational space and projection of side-chains along multiple vectors. The foldamers were rapidly constructed via an iterative deprotection-cross-coupling sequence, and their solid- and solution-phase conformations were analysed by X-ray crystallography and NMR and CD spectroscopy. These molecules may find applications in protein surface recognition where the interface does not involve canonical peptide secondary structures.

Stereoselective synthesis of quaternary center bearing azetines and their β-amino acid derivatives

(Chemical Equation Presented) We describe here the use of a stable, four-membered azetine heterocycle for the preparation of highly substituted β-amino acid derivatives. Imidazolidinone chiral auxiliaries were found to eliminate a competitive reaction pathway that had been present under previously reported conditions for azetine synthesis. The ephedrine derived imidazolidin-2-one 21 was allowed to react as its chlorotitanium enolate with O-methyl or -benzyl oximes under optimized conditions to gain improved access to azetines at the gram scale. The azetines were further found to undergo alkylation with complete diastereocontrol, affording the creation of a quaternary center. Subsequent ring opening with benzoyl chloride and auxiliary cleavage provided the corresponding β2,2,3-amino carbonyl derivatives in good yields.

Investigation of the Mitsunobu reaction of N-(2-hydroxyethyl)-N'- phenyl-ureas

The Mitsunobu reaction of N-(2-hydroxyethyl)-ureas 1 using PPh3 and EtO2CN=NCO2Et led to the mixture of N- and O-alkylation products or a single isomer depending on the substrates.