16638-85-0

Usage

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

• 67462-20-8 (1R,2S)-N-amino-2-methylamino-1-phenyl-1-propanol 
• 530-62-1 1,1'-carbonyldiimidazole 
• 105-58-8 Diethyl carbonate 
• 397332-07-9 (5S,6R)-4,5-dimethyl-6-phenyl-3-propionyl-3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-one 
• 104-88-1 4-chlorobenzaldehyde 
• 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 
• 66-99-9 β-naphthaldehyde 
• 620-23-5 m-tolyl aldehyde 
• 1850-89-1 (1S,2S)-N-amino-2-methylamino-1-phenyl-1-propanol 
• 321-98-2 (1S,2R)-(+)-ephedrine 
• 90-81-3 ephedrine 
• 7181-48-8 (1R,2S)-N-nitrosoephedrine 
• 1850-88-0 (1S,2S)-2-amino-N-methyl-N-nitroso-1-phenyl-1-propanol 
• 90-82-4 pseudoephedrine 

Relevant academic research and scientific papers

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-

Towards the development of oxadiazinanones as chiral auxiliaries: synthesis and application of N3-haloacetyloxadiazinanones

Oxadiazinanones derived from (1R,2S)-ephedrine and (1R,2S)-norephedrine were employed in the asymmetric α-halo aldol reaction. The optimized yields and diastereoselectivities for the ephedrine based oxadiazinanone aldol reaction ranged from fair to good.

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

Synthesis of 3,4,5,6-Tetrahydro-2H-1,3,4-oxadiazin-2-ones Employing a Metal Hydride and Diethyl Carbonate: An Alternative Cyclization Method over 1,1′-Carbonyldiimidazole

A series of 3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-ones have been synthesized from valine, leucine, ephedrine, and norephedrine. The synthesis is accomplished through a process of nitrosation, reduction, and cyclization. The cyclization protocol employed involves the use of a metal hydride (LiH or NaH) and diethyl carbonate rather than 1,1′-carbonyldiimidazole.

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.

Toward the development of a structurally novel class of chiral auxiliaries: Diastereoselective Aldol reactions of a (1R,2S)-ephedrine-based 3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-one

(equation Presented) 8 examples Asymmetric aldol addition reactions have been conducted with (1R,2S)-ephedrine-derived 3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-one (2). Diastereoselectivities range from 75:25 to 99:1 for the formation of the crude non-Evan

X-ray crystallographic and 13C nuclear magnetic resonance studies of 3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-ones derived from ephedrine and pseudoephedrine

3,4,5,6-Tetrahydro-2H-1,3,4-oxadiazin-2-ones derived from (1R,2S)-ephedrine and (1S,2S)-pseudoephedrine have been synthesized and their conformational properties have been examined. The ephedrine heterocycles 5-7a appear to favor one set of equilibrating