121269-45-2

Basic information

• Product Name: (5R)-3,4,5,6-Tetrahydro-5-phenyl-4(H)-1,4-oxazin-2-one
• Synonyms: (5R)-3,4,5,6-TETRAHYDRO-5-PHENYL-2(H)-1,4-OXAZIN-2-ONE;(5R)-3,4,5,6-TETRAHYDRO-5-PHENYL-4(H)-1,4-OXAZIN-2-ONE;R-5-PHENYL-MORPHOLIN-2-ONE;(5R)-5-phenylMorpholin-2-one;(R)-5-Phenyl-morpholin-2-one HCl;(5R)-3,4,5,6-TETRAHYDRO-5-PHENYL-4(H)-1,4-OXAZIN-2,-ONE(RS20013826)
• CAS NO: 121269-45-2
• Molecular Formula: C₁₀H₁₁NO₂
• Molecular Weight: 177.2
• Mol File: 121269-45-2.mol

Chemical Properties

• Melting Point: 53.5-54.5 °C
• Boiling Point: 364.33 °C at 760 mmHg
• Flash Point: 174.141 °C
• Appearance: /
• Density: 1.149 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.535
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• PKA: 6.14±0.40(Predicted)
• CAS DataBase Reference: (5R)-3,4,5,6-Tetrahydro-5-phenyl-4(H)-1,4-oxazin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (5R)-3,4,5,6-Tetrahydro-5-phenyl-4(H)-1,4-oxazin-2-one(121269-45-2)
• EPA Substance Registry System: (5R)-3,4,5,6-Tetrahydro-5-phenyl-4(H)-1,4-oxazin-2-one(121269-45-2)

Safety Data

• Hazardous Substances Data: 121269-45-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(5R)-3,4,5,6-Tetrahydro-5-phenyl-4(H)-1,4-oxazin-2-one is used as a key intermediate in the synthesis of pharmaceutical compounds for its unique structural features. Its chiral nature allows for the development of enantiomer-specific drugs, which can exhibit different biological activities and reduce potential side effects.
Used in Drug Synthesis:
(5R)-3,4,5,6-Tetrahydro-5-phenyl-4(H)-1,4-oxazin-2-one is used as a building block in the creation of novel bioactive molecules, contributing to the advancement of drug discovery and development. Its heterocyclic structure provides a versatile platform for chemical modifications and functionalization, enabling the design of new therapeutic agents with improved pharmacological properties.
Used in Research and Development:
(5R)-3,4,5,6-Tetrahydro-5-phenyl-4(H)-1,4-oxazin-2-one serves as a valuable research tool in the study of heterocyclic chemistry and its applications in medicinal chemistry. It aids in understanding the structure-activity relationships of oxazinone-containing compounds and their potential therapeutic effects, guiding the development of more effective and safer drugs.

InChI:InChI=1/C10H11NO2/c12-10-6-11-9(7-13-10)8-4-2-1-3-5-8/h1-5,9,11H,6-7H2/t9-/m0/s1

Upstream product

• 620-72-4 phenyl 2-bromoacetate 
• 56613-80-0 D-2-phenylglycinol 
• 175226-64-9 (5S)-5-phenyl-5,6-dihydro-2H-1,4-oxazin-2-one 
• 116173-81-0 (R)-2-methyl-4-phenyl-Δ²-oxazoline 

Downstream Products

• 139730-42-0 2(R),6(R),7(S),8(R) 2-phenyl-1-aza-4-oxa<4.3.0^1,6>bicyclononan-5-one-7,8-dicarboxylic anhydride 
• 134872-86-9 2(R),6(R),7(S),8(R) 2-phenyl-1-aza-4-oxa<4.3.0^1,6>bicyclononan-5-one-7,8-dicarboximide 
• 139730-41-9 2(R),6(R),7(R),8(S)-N-<(5'(R)-phenylmorpholin-2-onyl)methyl>-2-phenyl-1-aza-4-oxa<4.3.0^1,6>bicyclononan-5-one-7,8-dicarboximide 
• 134932-45-9 N-methyl 2(R),6(R),7(R),8(S) 2-phenyl-1-aza-4-oxa<4.3.0^1,6>bicyclononan-5-one-7,8-dicarboximide 
• 134872-89-2 N-methyl 2(R),6(R),7(S),8(R) 2-phenyl-1-aza-4-oxa<4.3.0^1,6>bicyclononan-5-one-7,8-dicarboximide 
• 152972-17-3 (2R,8R,12S)-12-phenyl-1-aza-10-oxatricyclo<6.4.0.0^2,6>dodec-6-en-9-one 
• 119878-90-9 (5R)-4-(tert-butyloxycarbonyl)-5-phenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one 
• 121269-55-4 (5R)-2,3,5,6-tetrahydro-5-phenyl-N-benzyl-4H-1,4-oxazin-2-one 
• 139730-44-2 2(R),6(R),7(S),8(R),9(R) dimethyl 2,9-diphenyl-1-aza-4-oxa<4.3.0^1,6>bicyclononan-5-one-7,8-dicarboxylate 
• 139892-56-1 2(R),6(R),7(R),8(S) dimethyl 2-phenyl-1-aza-4-oxa<4.3.0^1,6>bicyclononan-5-one-7,8-dicarboxylate 
• 134872-90-5 2(R),6(R),7(S),8(R) dimethyl 2-phenyl-1-aza-4-oxa<4.3.0^1,6>bicyclononan-5-one-7,8-dicarboxylate 
• 121269-46-3 (5R)-2,3,5,6-tetrahydro-5-phenyl-N-(benzyloxycarbonyl)-4H-1,4-oxazin-2-one 
• 182316-01-4 (5R)-5,6-dihydro-5-phenyl-2H-1,4-oxazin-2-one-N-oxide 
• 182316-07-0 (1R,2S,6S,9R)-8-aza-7,11-dioxa-9-phenyltricyclo[6.4.0.0^2,6]dodecan-12-one 

Relevant articles and documents

METHODS FOR TREATING CHRONIC PAIN USING 3-ARYL-3-HYDROXY-2-AMINO-PROPIONIC ACID AMIDES, 3-HETEROARYL-3-HYDROXY-2-AMINO-PROPIONIC ACID AMIDES AND RELATED COMPOUNDS

Disclosed herein are methods of treating a patient suffering from one or more types of chronic pain using compounds of Formulas 1 and 2 wherein the variables have the meaning disclosed in the specification

Oxidative rearrangement of 2-substituted oxazolines. A novel entry to 5,6-dihydro-2H-1,4-oxazin-2-ones and morpholin-2-ones

A novel synthesis of 5,6-dihydro-2H-1,4-oxazin-2-ones by SeO2-promoted oxidative rearrangement of 2-alkyl- and 2-(arylmethyl)oxazolines is described. Yields are good to excellent (up to 94%) with the highest yields obtained for 2-arylmethyl- and 2-neopentyl-substituted oxazolines. This reaction provides convenient access to novel 5-aryl-substituted dihydrooxazinones in high yield. The latter compounds are important 'chiral glycine' synthons for asymmetric synthesis of α-amino acids. Since oxazolines are readily derived from carboxylic acids or their equivalents, this oxidative rearrangement constitutes an entry to synthesis of α-amino acids from carboxylic acids. A mechanism is proposed to account for the rearrangement involving a 'nitrilium to acylium' 1,2-migration.

Enantioselective Synthesis of α-Amino Acid Derivatives via the Stereoselective Alkylation of a Homochiral Glycine Enolate Synthon

A new synthetic method for the enantioselective preparation of α-amino acid derivatives is presented.The key step involves the diastereoselective alkylation of the new chiral glycine enolate synthons 7 and 8 providing alkylation adducts with de of > 97.6percent in good yields (73-90percent).The reactivities of the enolates of 7 and 8 were extraordinarily sensitive to the metal counterion and solvent.Experimental conditions are described to maintain high diastereoselectivities in the alkylation step for electrophiles varying from highly reactive (α-haloacetate esters) to less reactive (n-butyl iodide).The alkylation diastereoselectivities were established to be under kinetic control by equilibration experiments on selected alkylation products.A model is presented which hinges on an A(1,3) interaction between the termini of the N4-acyl protecting group and the C5-phenyl group of 7 and 8 which in turn dictates the ?-facial selectivity of the enolate.The model successfully accounts for the observed results and is corroborated by the conformation of an alkylation adduct as revealed by a single-crystal X-ray determination.A simple one-pot, three-step deprotection procedure provides the desired α-amino acid as the ethyl ester hydrochloride salts (60-80percent overall yield) with no attending racemization as determined by conversion of the amino acid esters to the corresponding (+)- or (-)-Mosher amides.

STEREOSELECTIVE ALKYLATION OF CHIRAL GLYCINE ENOLATE SYNTHONS. THE ENANTIOSELECTIVE SYNTHESIS O α-AMINO ACID DERIVATES

The highly stereoselective alkylation (percentde=99.6 to 97.6) o a new chiral glycine enolate synthon derived from D-2-phenylglycinol is described.Deprotection of the alkylation adducts in a one-pot, three-step procedure provides the ethyl ester hydrochloride salts of the corresponding α-amino acids with no attending racemization.