16638-85-0

Basic information

• Product Name: (5R,6S)-4,5-dimethyl-6-phenyl-1,3,4-oxadiazinan-2-one
• CAS NO: 16638-85-0
• Molecular Formula: C₁₁H₁₄N₂O₂
• Molecular Weight: 206.2411
• Mol File: 16638-85-0.mol
• Article Data: 8

Chemical Properties

• Density: 1.113g/cm³
• Refractive Index: 1.52
• CAS DataBase Reference: (5R,6S)-4,5-dimethyl-6-phenyl-1,3,4-oxadiazinan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (5R,6S)-4,5-dimethyl-6-phenyl-1,3,4-oxadiazinan-2-one(16638-85-0)
• EPA Substance Registry System: (5R,6S)-4,5-dimethyl-6-phenyl-1,3,4-oxadiazinan-2-one(16638-85-0)

Safety Data

• Hazardous Substances Data: 16638-85-0(Hazardous Substances Data)

Usage

Description

(5R,6S)-4,5-dimethyl-6-phenyl-1,3,4-oxadiazinan-2-one is a chiral chemical compound belonging to the class of oxadiazine derivatives. It features a cyclic structure with a five-membered ring composed of an oxygen and two nitrogen atoms. (5R,6S)-4,5-dimethyl-6-phenyl-1,3,4-oxadiazinan-2-one's stereochemistry is defined by two stereocenters at the 5th and 6th positions, with the 5R and 6S configurations. Its unique structural features suggest potential pharmaceutical applications, and it may possess biological activity. Further research is necessary to fully understand its potential uses and properties.

Uses

Used in Pharmaceutical Applications:
(5R,6S)-4,5-dimethyl-6-phenyl-1,3,4-oxadiazinan-2-one is used as a potential pharmaceutical agent due to its unique structural features and possible biological activity. Its chiral nature and oxadiazine ring system may contribute to its effectiveness in targeting specific biological pathways or receptors, making it a candidate for the development of new drugs.
Used in Chemical Research:
In the field of chemical research, (5R,6S)-4,5-dimethyl-6-phenyl-1,3,4-oxadiazinan-2-one serves as a subject for studying the synthesis, properties, and reactivity of chiral oxadiazine derivatives. Understanding its behavior in various chemical reactions can provide insights into the broader class of oxadiazine compounds and their potential applications.
Used in Drug Design and Development:
(5R,6S)-4,5-dimethyl-6-phenyl-1,3,4-oxadiazinan-2-one is used as a starting material or a structural motif in drug design and development. Its unique stereochemistry and ring system can be exploited to create novel molecules with specific biological activities, potentially leading to the discovery of new therapeutic agents.

Upstream product

• 100-52-7 benzaldehyde 
• 612817-40-0 (5S,6R)-3,4,5,6-tetrahydro-4,5-dimethyl-3-(2-phenoxyacetyl)-6-phenyl-2H-1,3,4-oxadiazin-2-one 
• 123-11-5 4-methoxy-benzaldehyde 
• 612817-42-2 (5S,6R)-3-(2-methoxyacetyl)-4,5-dimethyl-3,4,5,6-tetrahydro-6-phenyl-2H-1,3,4-oxadiazin-2-one 
• 299-42-3 ephedrine 
• 105-58-8 Diethyl carbonate 
• 90-81-3 ephedrine 
• 7181-48-8 (1R,2S)-N-nitrosoephedrine 
• 321-98-2 (1S,2R)-(+)-ephedrine 
• 1850-88-0 (1S,2S)-2-amino-N-methyl-N-nitroso-1-phenyl-1-propanol 
• 90-82-4 pseudoephedrine 
• 1850-89-1 (1S,2S)-N-amino-2-methylamino-1-phenyl-1-propanol 
• 530-62-1 1,1'-carbonyldiimidazole 
• 1850-61-9 (1R,2S)-N-methyl-N-nitroso-2-amino-1-phenyl-1-propanol 

Relevant articles and documents

An improved procedure for the asymmetric aldol reaction of the titanium enolate of an N3-propionyl-3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-one

The direct formation of the titanium enolate of N3-propionyl-3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-one has been achieved through complexation with titanium tetrachloride at 25°C, followed by deprotonation with triethylamine (-78 to 25°C). The preformed titanium enolate has been reacted with D2O/DCl to afford deuterated derivative 6 and also reacted with a series of aromatic and aliphatic aldehydes affording aldol adducts 4a-f with crude diastereoselectivities ranging from 8:1 to 38:1.

Formation of Complex Hydrazine Derivatives via Aza-Lossen Rearrangement

The development of a broadly applicable procedure for the aza-Lossen rearrangement is reported. This process converts amines into complex hydrazine derivatives in two steps under safe, mild conditions. This method allows the chemoselective formation of N-

Synthesis, X-ray crystallography and computational studies concerning an oxadiazinone derived from D-camphor: A structural limitation of oxadiazinones as chiral auxiliaries

A camphor-based oxadiazinone was prepared by reaction of the N-nitroimine of d-camphor with (1R,2S)-norephedrine; the reduction of the resultant imine; N-nitrosation of the amine; reduction to the corresponding hydrazine and cyclization. The conformationa

Oxadiazinones as chiral auxiliaries: Diastereoselective aldol addition reactions of N3-glycolyl-3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-ones

Asymmetric aldol reactions have been conducted with a series of N 3-glycolyl-3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-ones derived from (1R,2S)-ephedrine. These reactions afford the non-Evans syn-adducts in 43-97% yield and diastereoselectivities ranging from 62:38 to 99:1. Oxadiazinone substrates substituted with either the phenoxyacetyl or p-methoxyphenoxyacetyl groups gave the best results whereas the methoxyacetyl substituted oxadiazinone afforded diastereoselectivities that were modest.