(5S,7S)-3-aminoadamantan-1-ol

• ChemBase ID: 159796
• Molecular Formular: C10H17NO
• Molecular Mass: 167.24808
• Monoisotopic Mass: 167.13101417
• SMILES: C12(C[C@@H]3C[C@@H](C1)C[C@](C3)(C2)O)N
• Canonical SMILES: NC12C[C@@H]3C[C@@H](C1)C[C@](C2)(C3)O
• InChI: InChI=1S/C10H17NO/c11-9-2-7-1-8(3-9)5-10(12,4-7)6-9/h7-8,12H,1-6,11H2/t7-,8-,9?,10-/m0/s1
• InChIKey: DWPIPTNBOVJYAD-HQRIKABESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5S,7S)-3-aminoadamantan-1-ol
• IUPAC Traditional name: (5S,7S)-3-aminoadamantan-1-ol
• Synonyms: 3-Amino-1-adamantanol; 3-Amino-tricyclo[3.3.1.13,7]decan-1-ol; 1-Amino-3-hydroxyadamantane; (3-Hydroxyadamantan-1-yl)amine; 1-Amino-3-adamantanol

Database IDs

• CAS Number: 702-82-9
• PubChem SID: 162253931
• PubChem CID: 6944935

CALCULATED PROPERTIES

• Acid pKa: 14.705673
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -2.9483817
• LogD (pH = 7.4): -2.6029768
• Log P: 0.07794632
• Molar Refractivity: 47.1741 cm^3
• Polarizability: 19.106407 Å^3
• Polar Surface Area: 46.25 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: 251-257°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - A580300

Reagent used in the preparation of Vildagliptin.

REFERENCES

• Fukushima, H., et al.: Bioorg. Med. Chem., 16, 4093 (2008)
• Anand, R., et al.: J. Med. Chem., 52, 1602 (2008)