(6R)-6-[(R)-2-ethoxyphenoxy(phenyl)methyl]morpholin-3-one

• ChemBase ID: 168357
• Molecular Formular: C19H21NO4
• Molecular Mass: 327.37434
• Monoisotopic Mass: 327.14705816
• SMILES: c1cc(c(cc1)O[C@@H]([C@@H]1OCC(=O)NC1)c1ccccc1)OCC
• Canonical SMILES: CCOc1ccccc1O[C@H](c1ccccc1)[C@H]1CNC(=O)CO1
• InChI: InChI=1S/C19H21NO4/c1-2-22-15-10-6-7-11-16(15)24-19(14-8-4-3-5-9-14)17-12-20-18(21)13-23-17/h3-11,17,19H,2,12-13H2,1H3,(H,20,21)/t17-,19-/m1/s1
• InChIKey: BXLPJKGEJVAHON-IEBWSBKVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R)-6-[(R)-2-ethoxyphenoxy(phenyl)methyl]morpholin-3-one
• IUPAC Traditional name: (6R)-6-[(R)-2-ethoxyphenoxy(phenyl)methyl]morpholin-3-one
• Synonyms: (6R)-rel-6-[(R)-(2-Ethoxyphenoxy)phenylmethyl]-3-morpholinone; (R*,R*)-(+/-)-6-[(R)-(2-Ethoxyphenoxy)phenylmethyl]-3-morpholinone; 6-[(2-Ethoxyphenoxy)phenylmethyl]-3-morpholinone; rel-(2R,3R)-6-[α-(2-Ethoxyphenoxy)benzyl]morpholin-3-one

Database IDs

• CAS Number: 98769-79-0
• PubChem SID: 162262489
• PubChem CID: 29979578

CALCULATED PROPERTIES

• Acid pKa: 12.775506
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.5349348
• LogD (pH = 7.4): 2.534933
• Log P: 2.5349348
• Molar Refractivity: 89.564 cm^3
• Polarizability: 35.335262 Å^3
• Polar Surface Area: 56.79 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Benzene; Dichloromethane; Ethyl Acetate; Toluene
• Apperance: Off-White to Yellow Solid
• Melting Point: 108-111°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - E892650

An intermediate in the synthesis of Reboxetine (R142000).

REFERENCES

• Melloni, P., et al.: Tetrahedron, 41, 1393 (1985)