7693-77-8

Basic information

• Product Name: Resedine
• Synonyms: 5-Phenyl-2-oxazolidone;Resedine;5-Phenyl-2-oxazolidinone;5-Phenyloxazolidin-2-one;5-phenyl-1,3-oxazolidin-2-one
• CAS NO: 7693-77-8
• Molecular Formula: C₉H₉NO₂
• Molecular Weight: 163.17326
• Product Categories: Heterocycles series
• Mol File: 7693-77-8.mol
• Article Data: 61

Chemical Properties

• Boiling Point: 407 °C at 760 mmHg
• Flash Point: 200 °C
• Appearance: /
• Density: 1.195 g/cm³
• Vapor Pressure: 7.79E-07mmHg at 25°C
• Refractive Index: 1.548
• CAS DataBase Reference: Resedine(CAS DataBase Reference)
• NIST Chemistry Reference: Resedine(7693-77-8)
• EPA Substance Registry System: Resedine(7693-77-8)

Safety Data

• Hazardous Substances Data: 7693-77-8(Hazardous Substances Data)

Usage

Description

A simple alkaloid, resedine has recently been isolated and characterized byRussian workers who have obtained it from Reseda luteola. The structure given has been elucidated on the basis of ultraviolet, infrared, NMR and mass spectra. Alkaline hydrolysis furnishes 2-hydroxyphenethylamine.

Synthesis Reference(s)

Tetrahedron Letters, 40, p. 6059, 1999 DOI: 10.1016/S0040-4039(99)01256-3

References

Tadzhibaev et al., Khim. Prir. Soedin., 12,270 (1976)

InChI:InChI=1/C9H9NO2/c11-9-10-6-8(12-9)7-4-2-1-3-5-7/h1-5,8H,6H2,(H,10,11)

Upstream product

• 100-42-5 styrene 
• 13698-16-3 ethyl N,N-dichlorocarbamate 
• 39547-65-4 5-methyl-3-nitroso-2-oxazolidinone 
• 70197-04-5 1-ethoxycarbonyl-2-phenylaziridine 
• 7568-93-6 2-Amino-1-phenylethanol 
• 7007-19-4 N-benzoyl-5-phenyl-oxazolidin-2-one 
• 57-13-6 urea 
• 24506-17-0 3-hydroxy-3-phenylpropionamide 
• 75-44-5 phosgene 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 96-09-3 styrene oxide 
• 917-61-3 sodium isocyanate 
• 4248-19-5 tert-butyl carbazate 
• 197020-64-7 (+/-)-(N-tert-Butoxycarbonyl)-2-phenylaziridine 

Downstream Products

• 86238-44-0 N-<(R)-1-(1-Naphthyl)ethyl>-(5S)-phenyl-2-oxazolidone-3-carboxamide 
• 86217-49-4 N-<(R)-1-(1-Naphthyl)ethyl>-(5R)-phenyl-2-oxazolidone-3-carboxamide 
• 7007-19-4 N-benzoyl-5-phenyl-oxazolidin-2-one 
• 1019650-97-5 3-(2-aminopyridin-4-yl)-5-phenyl-1,3-oxazolidin-2-one 
• 1019648-91-9 N-(4-(2-oxo-5-phenyl-1,3-oxazolidin-3-yl)pyridin-2-yl)-N'-(pyridin-2-ylmethyl)urea 
• 1019651-24-1 bis(2,2,2-trichloroethyl)(4-(2-oxo-5-phenyl-1,3-oxazolidin-3-yl)pyridin-2-yl)imidodicarbonate 
• 1325189-13-6 3-[7-(4-methylpiperazin-1-yl)furo[2,3-c]pyridin-5-yl]-5-phenyl-1,3-oxazolidin-2-one 

Relevant articles and documents

Identification of (6S)-cyclopropyl-6,7-dihydropyrazolo[1,5-a]pyrazine-5(4H)-carboxamines as new HBV capsid assembly modulators

GYH2-18 is a type II HBV CAM with 6,7-dihydropyrazolo[1,5-a]pyrazine-5(4H)-carboxamine (DPPC) skeleton discovered by Roche INC. A series of GYH2-18 derivatives were designed, synthesized and evaluated for their anti-HBV activity. Two compounds 2f and 3k exhibited excellent anti-HBV activity, low cytotoxicity and accepted oral PK profiles. Chiral separation of 2f and 3k was conducted successfully, and (6S)-cyclopropyl DPPC isomers 2f-1, 2f-3, 3k-1 and 3k-3 were identified to be much more active than the corresponding (6R)-ones. The preliminary structure-activity relationship, particle gel assay and molecular modeling studies were also discussed, which provide useful indications for guiding the further rational design of new (6S)-cyclopropyl DPPC analogues.

Diethylammonium iodide as catalyst for the metal-free synthesis of 5-aryl-2-oxazolidinones from aziridines and carbon dioxide

The catalytic potential of ammonium halide salts was explored in the coupling reaction of a model aziridine with carbon dioxide, highlighting the superior activity of [NH2Et2]I. Then, working at room temperature, atmospheric CO2 pressure and in the absenc

Regioselective Ring-Opening of Styrene Oxide Derivatives Using Halohydrin Dehalogenase for Synthesis of 4-Aryloxazolidinones

A biocatalytic approach towards a range of 4-aryloxazolidinones is developed using a halohydrin dehalogenase from Ilumatobacter coccineus (HheG) as biocatalyst. The method is based on the HheG-catalyzed α-position regioselective ring-opening of styrene oxide derivatives with cyanate as a nucleophile, producing the corresponding 4-aryloxazolidinones in moderate to good yields. Synthesis of enantiopure 4-aryloxazolidinones is also achievable using chiral epoxide materials. (Figure presented.).