144538-22-7

Basic information

• Product Name: (5S,6R)-5,6-Diphenyl-2-morpholinone
• Synonyms: (5S,6R)-5,6-Diphenyl-2-morpholinone;(5S,6R)-2,3,5,6-tetrahydro-5,6- diphenyl-1,4-oxazin;5S,6R-Diphenyl-2-morpholinone;(5S,6R)-5,6-DiphenylMorpholin-2-one;(5S,6R)-Diphenyl-2-morpholinone,99%e.e.
• CAS NO: 144538-22-7
• Molecular Formula: C₁₆H₁₅NO₂
• Molecular Weight: 253.2958
• Product Categories: Heterocycles;Chiral Reagents
• Mol File: 144538-22-7.mol

Chemical Properties

• Boiling Point: 444°C
• Flash Point: 222.348 °C
• Appearance: /Solid
• Density: 1.159
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.577
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 5.68±0.60(Predicted)
• CAS DataBase Reference: (5S,6R)-5,6-Diphenyl-2-morpholinone(CAS DataBase Reference)
• NIST Chemistry Reference: (5S,6R)-5,6-Diphenyl-2-morpholinone(144538-22-7)
• EPA Substance Registry System: (5S,6R)-5,6-Diphenyl-2-morpholinone(144538-22-7)

Safety Data

• Hazardous Substances Data: 144538-22-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(5S,6R)-5,6-Diphenyl-2-morpholinone is used as a key intermediate in the synthesis of (+)and (-)-spirotryprostatin B, which are complex organic molecules with potential pharmaceutical applications. The stereoselective 1,3-dipolar cycloaddition reaction involving (5S,6R)-5,6-Diphenyl-2-morpholinone allows for the creation of novel molecules with specific biological activities, making it a valuable tool in the development of new drugs and therapeutic agents.

InChI:InChI=1/C16H15NO2/c18-14-11-17-15(12-7-3-1-4-8-12)16(19-14)13-9-5-2-6-10-13/h1-10,15-17H,11H2/t15-,16+/m0/s1

Upstream product

• 112741-49-8 tert-butyl (2R,3S)-6-oxo-2,3-diphenylmorpholine-4-carboxylate 

Downstream Products

• 144436-67-9 (2S,5R,6S,8R,9R)-5,6-diphenyl-8,9-dicarbomethoxy-1-aza-4-oxabicyclo<4.3.0>nonan-3-one 
• 282735-73-3 (3R,3'R,4'S,6'R,8'S,8'aS)-1,2,3',4',8',8a'-hexahydro-6'-(2-methoxy-2-methylpropyl)-1',2-dioxo-3',4'-diphenylspiro[3H-indole-3,7'(6'H)-[1H]pyrrolo[2,1-c][1,4]oxazine]-8'-carboxylic acid ethyl ester 
• 897365-80-9 (2'S,3'R,4'R,5'S)-6-Chloro-4'-(3-chloro-2-fluoro-phenyl)-2'-(2,2-dimethyl-propyl)-1'-((1S,2R)-2-hydroxy-1,2-diphenyl-ethyl)-2-oxo-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-5'-carboxylic acid (2-morpholin-4-yl-ethyl)-amide 
• 214628-38-3 (5S,6R)-4-Oxy-5,6-diphenyl-5,6-dihydro-[1,4]oxazin-2-one 
• 144538-23-8 (2S,5R,6S,8R,9R)-5,6-diphenyl-7(S)-ethyl-8,9-dicarbomethoxy-1-aza-4-oxabicyclo<4.3.0>nonan-3-one 
• 144436-70-4 (2S,5R,6S,8R,9R)-5,6,7-triphenyl-8,9-dicarbomethoxy-1-aza-4-oxabicyclo<4.3.0>nonan-3-one 

Relevant articles and documents

Asymmetric, stereocontrolled total synthesis of (+) and (-)-spirotryprostatin B via a diastereoselective azomethine ylide [1,3]-dipolar cycloaddition reaction

The asymmetric, stereocontrolled total syntheses of (+) and (-)-spirotryprostatin B (2) are described. Formation of the core pyrrolidine ring was accomplished via a diastereoselective asymmetric [1,3]-dipolar cycloaddition reaction. Addition of 3-methoxy-

Asymmetric -Dipolar Cycloaddition Reactions: Synthesis of Highly Substituted Proline Derivatives

The asymmetric -dipolar cycloaddition reactions of azomethine ylides derived from (5R,6S)-2,3,5,6-tetrahydro-5,6-diphenyl-1,4-oxazin-2-one with various aldehydes and dimethyl maleate is described.The reactions prove to be highly endo-selective, installing three contiguous stereogenic centers in the newly formed five-membered ring with essentially complete stereochemical control.In the case of aldehydes higher than formaldehyde, a fourth stereogenic center is created; in most cases, poor stereoselectivity is observed at this center; the diastereomers formed in these cases can be separated by chromatography and separately converted into the amino acids.The bicyclic dipolar adducts can be cleaved with either catalytic hydrogenolysis or hydrolytic ring opening, esterification, and lead tetraacetate removal of the chiral auxiliary.