(2S,3R)-3-(2-ethoxyphenoxy)-3-phenylpropane-1,2-diol

• ChemBase ID: 168359
• Molecular Formular: C17H20O4
• Molecular Mass: 288.3383
• Monoisotopic Mass: 288.13615912
• SMILES: c1cc(c(cc1)O[C@@H]([C@H](CO)O)c1ccccc1)OCC
• Canonical SMILES: CCOc1ccccc1O[C@H](c1ccccc1)[C@H](CO)O
• InChI: InChI=1S/C17H20O4/c1-2-20-15-10-6-7-11-16(15)21-17(14(19)12-18)13-8-4-3-5-9-13/h3-11,14,17-19H,2,12H2,1H3/t14-,17+/m0/s1
• InChIKey: XSHMFDVTMXNQSJ-WMLDXEAASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R)-3-(2-ethoxyphenoxy)-3-phenylpropane-1,2-diol
• IUPAC Traditional name: (2S,3R)-3-(2-ethoxyphenoxy)-3-phenylpropane-1,2-diol
• Synonyms: (2R,3S)-rel-3-(2-Ethoxyphenoxy)-3-phenyl-1,2-propanediol; (R*,S*)-(+/-)-3-(2-Ethoxyphenoxy)-3-phenyl-1,2-propanediol; (2RS,3RS)-3-(2-Ethoxyphenoxy)-1,2-dihydroxy-3-phenylpropane

Database IDs

• CAS Number: 98769-69-8
• PubChem SID: 162262491
• PubChem CID: 57354869

CALCULATED PROPERTIES

• Acid pKa: 13.285068
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.4785144
• LogD (pH = 7.4): 2.478514
• Log P: 2.4785144
• Molar Refractivity: 80.2706 cm^3
• Polarizability: 31.715826 Å^3
• Polar Surface Area: 58.92 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: White Solid
• Melting Point: 78-79°C

DETAILS

Toronto Research Chemicals - E892660

An intermediate in the synthesis of Reboxetine (R142000).

REFERENCES

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