5-hydroxyadamantan-2-one

• ChemBase ID: 24952
• Molecular Formular: C10H14O2
• Molecular Mass: 166.21696
• Monoisotopic Mass: 166.09937969
• SMILES: C1(=O)C2CC3(CC1CC(C2)C3)O
• Canonical SMILES: O=C1C2CC3CC1CC(C2)(C3)O
• InChI: InChI=1S/C10H14O2/c11-9-7-1-6-2-8(9)5-10(12,3-6)4-7/h6-8,12H,1-5H2
• InChIKey: TZBDEVBNMSLVKT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-hydroxyadamantan-2-one
• IUPAC Traditional name: kemantan; 5-hydroxyadamantan-2-one
• Synonyms: 5-Hydroxyadamantan-2-one; Kemantane; Idramantone

Database IDs

• CAS Number: 20098-14-0
• MDL Number: MFCD00192211
• PubChem SID: 160988259
• PubChem CID: 64184

CALCULATED PROPERTIES

• Acid pKa: 14.722116
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.905546
• LogD (pH = 7.4): 0.90554595
• Log P: 0.905546
• Molar Refractivity: 44.5713 cm^3
• Polarizability: 17.664183 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 300 - 302°C
• Hydrophobicity(logP): -0.072

Safety Information

• Storage Warning: IRRITANT; Irritant
• TSCA Listed: false

Pharmacology Properties

• Mechanism of Action: T-cell suppressor

Product Information

• Purity: 95%; 97%
• Application(s): Lymphocyte and antibody stimulant in mice

REFERENCES

• Geluk, H.W. et al., Tetrahedron, 1968, 24, 5369, (synth, ir, pmr)
• Geluk, H.W., Synthesis, 1972, 374, (synth)
• Vodicka, L. et al., Coll. Czech. Chem. Comm., 1975, 40, 293, (pmr)
• Czech. Pat., 1976, 163 671; CA, 86, 55081h, (synth)
• Lantvoev, V.I., Zh. Org. Khim., 1976, 12, 236; J. Org. Chem. USSR (Engl. Transl.), 1976, 12, 2292, (synth, ir)
• Morat, C. et al., Tet. Lett., 1979, 4409, (synth, Ac, ir, pmr, cmr)
• Le Noble, W.J. et al., J.O.C., 1983, 48, 1099, (synth)
• Bolte, G. et al., Chem. Ber., 1984, 117, 1982, (synth, pmr, ir, ms)
• Srivastava, S. et al., Synth. Commun., 1984, 14, 65, (synth, bibl)
• Boiko, S.S. et al., CA, 1991, 115, 84695, (glc)