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

• ChemBase ID: 168363
• Molecular Formular: C25H25NO9S
• Molecular Mass: 515.5323
• Monoisotopic Mass: 515.12500239
• SMILES: c1cc(c(cc1)O[C@@H]([C@H](COC(=O)c1ccc(cc1)[N+](=O)[O-])OS(=O)(=O)C)c1ccccc1)OCC
• Canonical SMILES: CCOc1ccccc1O[C@@H]([C@@H](OS(=O)(=O)C)COC(=O)c1ccc(cc1)[N+](=O)[O-])c1ccccc1
• InChI: InChI=1S/C25H25NO9S/c1-3-32-21-11-7-8-12-22(21)34-24(18-9-5-4-6-10-18)23(35-36(2,30)31)17-33-25(27)19-13-15-20(16-14-19)26(28)29/h4-16,23-24H,3,17H2,1-2H3/t23-,24+/m0/s1
• InChIKey: MKHNDUASQGQRFX-BJKOFHAPSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 98854-88-7
• PubChem SID: 162262495
• PubChem CID: 71316529

CALCULATED PROPERTIES

• H Acceptors: 7
• H Donor: 0
• LogD (pH = 5.5): 4.8499627
• LogD (pH = 7.4): 4.8499627
• Log P: 4.8499627
• Molar Refractivity: 130.1698 cm^3
• Polarizability: 51.307762 Å^3
• Polar Surface Area: 133.95 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate
• Apperance: Yellow Solid
• Melting Point: 118-120°C

DETAILS

Toronto Research Chemicals - E892680

An intermediate in the synthesis of Reboxetine (R142000).

REFERENCES

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