(R)-5-phenylmorpholin-2-one

Base Information

• Chemical Name: (R)-5-phenylmorpholin-2-one
• CAS No.: 121269-45-2
• Molecular Formula: C10H11NO2
• Molecular Weight: 177.203
• DSSTox Substance ID: DTXSID80456127
• Nikkaji Number: J998.118G
• Wikidata: Q72506533
• Mol file: 121269-45-2.mol

Synonyms:121269-45-2;(R)-5-phenylmorpholin-2-one;(5R)-5-PHENYLMORPHOLIN-2-ONE;(5R)-3,4,5,6-tetrahydro-5-phenyl-4(H)-1,4-oxazin-2-one;(R)-5-Phenyl-morpholin-2-one;5alpha-Phenylmorpholine-2-one;SCHEMBL739240;(R)-5-Phenylmorpholine-2-One;DTXSID80456127;CMYHFJFAHHKICH-VIFPVBQESA-N;MFCD00269692;AKOS006275519;AKOS015855488;PS-16453;CS-0442401;EN300-4274923;(5R)-3,4,5,6-Tetrahydro-5-phenyl-2(H)-1,4-oxazin-2-one

Chemical Property of (R)-5-phenylmorpholin-2-one

Chemical Property:

• Appearance/Colour: White crystalline
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 53.5-54.5 °C
• Refractive Index: 1.535
• Boiling Point: 364.33 °C at 760 mmHg
• PKA: 6.14±0.40(Predicted)
• Flash Point: 174.141 °C
• PSA: 38.33000
• Density: 1.149 g/cm³
• LogP: 1.20290
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 177.078978594
• Heavy Atom Count: 13
• Complexity: 187

Purity/Quality:

97% ^*data from raw suppliers

(R)-5-Phenylmorpholin-2-one 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(NCC(=O)O1)C2=CC=CC=C2
• Isomeric SMILES: C1[C@H](NCC(=O)O1)C2=CC=CC=C2

Technology Process of (R)-5-phenylmorpholin-2-one

There total 4 articles about (R)-5-phenylmorpholin-2-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 78.0%

phenyl 2-bromoacetate (620-72-4) + D-2-phenylglycinol (56613-80-0) → (R)-5-phenyl-3,4,5,6-tetrahydro-2H-1,4-oxazin-2-one (121269-45-2,134872-85-8)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; for 18h; Ambient temperature;

DOI:10.1021/jo00277a032

Reference yield:

(5S)-5-phenyl-5,6-dihydro-2H-1,4-oxazin-2-one (175226-64-9) → (R)-5-phenyl-3,4,5,6-tetrahydro-2H-1,4-oxazin-2-one (121269-45-2,134872-85-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 3h; under 760 Torr; Yield given; Ambient temperature;

DOI:10.1021/jo952144f

Reference yield:

D-2-phenylglycinol (56613-80-0) → (R)-5-phenyl-3,4,5,6-tetrahydro-2H-1,4-oxazin-2-one (121269-45-2,134872-85-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent

2: 72 percent / selenium dioxide / dioxane / 2 h / Heating

3: hydrogen / 10percent Pd-C / ethyl acetate / 3 h / 760 Torr / Ambient temperature

With selenium(IV) oxide; hydrogen; palladium on activated charcoal; In 1,4-dioxane; ethyl acetate;

DOI:10.1021/jo952144f

upstream raw materials:

phenyl 2-bromoacetate

D-2-phenylglycinol

(5S)-5-phenyl-5,6-dihydro-2H-1,4-oxazin-2-one

(R)-2-methyl-4-phenyl-Δ²-oxazoline

Downstream raw materials:

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

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

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

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