(2S,3R)-3-(2-ethoxyphenoxy)-2-hydroxy-3-phenylpropyl 4-nitrobenzoate

• ChemBase ID: 168361
• Molecular Formular: C24H23NO7
• Molecular Mass: 437.44192
• Monoisotopic Mass: 437.14745208
• SMILES: c1cc(c(cc1)O[C@@H]([C@H](COC(=O)c1ccc(cc1)[N+](=O)[O-])O)c1ccccc1)OCC
• Canonical SMILES: CCOc1ccccc1O[C@H](c1ccccc1)[C@H](COC(=O)c1ccc(cc1)[N+](=O)[O-])O
• InChI: InChI=1S/C24H23NO7/c1-2-30-21-10-6-7-11-22(21)32-23(17-8-4-3-5-9-17)20(26)16-31-24(27)18-12-14-19(15-13-18)25(28)29/h3-15,20,23,26H,2,16H2,1H3/t20-,23+/m0/s1
• InChIKey: WDILXXVWAWRMBW-NZQKXSOJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R)-3-(2-ethoxyphenoxy)-2-hydroxy-3-phenylpropyl 4-nitrobenzoate
• IUPAC Traditional name: (2S,3R)-3-(2-ethoxyphenoxy)-2-hydroxy-3-phenylpropyl 4-nitrobenzoate
• Synonyms: (2R,3S)-rel-3-(2-Ethoxyphenoxy)-3-phenyl-1,2-propanediol 1-(4-Nitrobenzoate); (R*,S*)-(+/-)-3-(2-Ethoxyphenoxy)-3-phenyl-1,2-propanediol 1-(4-Nitrobenzoate); (2RS,3RS)-3-(2-Ethoxyphenoxy)-2-hydroxy-1-(4-nitrobenzoyloxy)-3-phenylpropane

Database IDs

• CAS Number: 98769-70-1
• PubChem SID: 162262493
• PubChem CID: 71316527

CALCULATED PROPERTIES

• Acid pKa: 13.271836
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 4.9137983
• LogD (pH = 7.4): 4.913798
• Log P: 4.9137983
• Molar Refractivity: 117.4173 cm^3
• Polarizability: 45.156048 Å^3
• Polar Surface Area: 110.81 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate
• Apperance: Yellow Solid
• Melting Point: 94-95°C

DETAILS

Toronto Research Chemicals - E892665

An intermediate in the synthesis of Reboxetine (R142000).0

REFERENCES

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