(1R)-2-amino-1-[(2S)-6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl]ethan-1-ol

• ChemBase ID: 160291
• Molecular Formular: C11H14FNO2
• Molecular Mass: 211.2327632
• Monoisotopic Mass: 211.10085691
• SMILES: c1c(cc2c(c1)O[C@@H](CC2)[C@@H](CN)O)F
• Canonical SMILES: NC[C@H]([C@@H]1CCc2c(O1)ccc(c2)F)O
• InChI: InChI=1S/C11H14FNO2/c12-8-2-4-10-7(5-8)1-3-11(15-10)9(14)6-13/h2,4-5,9,11,14H,1,3,6,13H2/t9-,11+/m1/s1
• InChIKey: XEWOKAJCYBGRTK-KOLCDFICSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R)-2-amino-1-[(2S)-6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl]ethan-1-ol
• IUPAC Traditional name: (1R)-2-amino-1-[(2S)-6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl]ethanol
• Synonyms: (2S,αR)-α-(Aminomethyl)-6-fluoro-chroman-2-methanol; (2S,αR)-α-(Aminomethyl)-6-fluoro-3,4-dihydro-2H-1-benzopyran-2-methanol

Database IDs

• CAS Number: 303176-42-3
• PubChem SID: 162254426
• PubChem CID: 11458498

CALCULATED PROPERTIES

• Acid pKa: 13.830478
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -1.891015
• LogD (pH = 7.4): -0.8095001
• Log P: 1.075182
• Molar Refractivity: 54.2307 cm^3
• Polarizability: 21.240446 Å^3
• Polar Surface Area: 55.48 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Methanol
• Apperance: Off-White Solid
• Melting Point: 109-112°C

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A616195

(+)-Nebivolol intermediate.

REFERENCES

• Bowden, C., et al.: J. Pharmacol. Exp. Ther., 251, 599 (1989)