38014-52-7

Usage

InChI:InChI=1/C5H12N2O/c1-3-4-7-5(8)6-2/h3-4H2,1-2H3,(H2,6,7,8)

Upstream product

• 107-10-8 propylamine 
• 624-83-9 methyl isocyanate 
• 110-78-1 Propyl isocyanate 
• 74-89-5 methylamine 
• 84996-79-2 7-cyano-1-imino-2-methyl-2,3-dihydro-1H-imidazo<3,4-c>imidazol-3-one 
• 64-17-5 ethanol 
• 556-61-6 methyl thioisocyanate 
• 13256-32-1 1,3 dimethyl 1 nitrosourea 

Downstream Products

• 53681-48-4 6-amino-3-methyl-1-propyl-1H-pyrimidine-2,4-dione 
• 118024-67-2 1-methyl-3-propylxanthine 
• 1255650-81-7 N-methyl-N-(propylcarbamoyl)benzamide 
• 1255650-82-8 N-(methylcarbamoyl)-N-propylbenzamide 

Relevant academic research and scientific papers

Inherently Chiral Bambus[4]urils

A new class of bambus[4]urils (BU[4]s) composed of asymmetric N,N′-disubstituted glycoluril subunits with different alkyl groups were designed, synthesized, and fully characterized by NMR techniques and X-ray crystallography. Structural studies showed that four macrocyclic diastereoisomers are possible: two Sn symmetric achiral macrocycles and two macrocycles that are inherently chiral. The relative head-to-tail arrangement of the N-substituents in Bn4Me4BU[4], 5a, clearly observed by X-ray spectroscopy analysis, determines the overall symmetry of the bambusuril structure. Chiral Pr4Me4BU[4], 4b, was resolved by chiral high-performance liquid chromatography (HPLC) into its enantiomers, and all four inherently chiral bambusuril pairs (two Pr4Me4BU[4] and two Bn4Me4BU[4] stereoisomers, 4b, 4d, 5b, and 5d) were clearly observed by 1H NMR spectroscopy with the aid of (R)-BINOL as a chiral solvating agent. This latter methodology provides a rapid and powerful approach for investigating the enantiopurity of inherently chiral cavitands, which complements and augments the conventional chromatographic approaches.

Reactions of 4,5-Dicyanoimidazoles with Isocyanates. Novel Formation of the Condensed Tricyclic Imidazoles

The reactions of 4,5-dicyanoimidazoles with methyl isocyanate gave 7-cyano-1-imino-2-methyl-2,3-dihydro-1H-imidazoimidazol-3-oens (2), while the similar reactions with phenyl isocyanate resulted in the formation of the tricyclic imidazoles, 11-imino-6,10-diphenyl-2,4,6,8,10-pentaazatricyclo4,12>dodeca-1(12),2,7-triene-5,9-diones (3) and the same type of the tricyclic imidazoles 4 were obtained by carbamoylation of 2 with phenyl isocyanate.The reactions of 2, 3, and 4 with amines were further investigated.

Conformational Preferences in Alkylnitrosoureas

The spectroscopic properties of several N-alkyl-N-nitrosoureas, N,N'-dialkyl-N-nitrosoureas, and N,N',N'-trialkyl-N-nitrosoureas have been studied in carbon disulfide and chloroform solutions.The NH stretching frequencies in the IR spectra have been observed in both concentrated and dilute solution and in the presence of added dioxane.The results indicate that there is a strong intramolecular hydrogen bond in the mono- and dialkylnitrosoureas.The chemical shifts and line widths of the NMR spectra have also been studied in these solvents.The large chemical shift differences, about 1.3 ppm, for the NH protons in the monoalkylnitrosoureas and other spectroscopic features in the monoalkyl- and dialkylnitrosoureas also indicate that an intramolecular hydrogen bond contributes to a strong conformational preference.The temperature dependence of the NMR spectra of several N,N',N'-trialkyl-N-nitrosoureas establishes that the energy barrier for rotation about the carbon dialkylamide bond is about 13 kcal mol-1.Dipolar resonance interactions are primarily responsible for this barrier.This interaction is augmented by a strong, 8-10 kcal mol-1, hydrogen bond in the mono- and dialkylnitrosoureas.