adamantan-1-ol

• ChemBase ID: 85771
• Molecular Formular: C10H16O
• Molecular Mass: 152.23344
• Monoisotopic Mass: 152.12011513
• SMILES: OC12CC3CC(C1)CC(C2)C3
• Canonical SMILES: OC12CC3CC(C2)CC(C1)C3
• InChI: InChI=1S/C10H16O/c11-10-4-7-1-8(5-10)3-9(2-7)6-10/h7-9,11H,1-6H2
• InChIKey: VLLNJDMHDJRNFK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: adamantan-1-ol
• IUPAC Traditional name: 1-hydroxyadamantane
• Synonyms: 1-Hydroxyadamantane; 1-Adamantanol; Adamantan-1-ol; (3s,5s,7s)-adamantan-1-ol; 1-金刚醇

Database IDs

• CAS Number: 768-95-6
• EC Number: 212-202-8
• MDL Number: MFCD00074729
• Beilstein Number: 1903952
• PubChem SID: 162072887
• PubChem CID: 64152

CALCULATED PROPERTIES

• Acid pKa: 19.73935
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 1.5728291
• LogD (pH = 7.4): 1.5728294
• Log P: 1.5728294
• Molar Refractivity: 43.8781 cm^3
• Polarizability: 17.579895 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 245-247(subl.)°C; ca 245°C subl.

Safety Information

• Storage Warning: Irritant
• RTECS: AU4980000
• TSCA Listed: 否

Product Information

• Purity: 99%

REFERENCES

• Carboxyl groups of amino acids have been protected as 1-adamantyl esters via the amino acid tosylate and dimethyl sulfite. The group is readily cleaved with TFA under mild conditions: Synthesis, 1355 (1996). Has also been applied in blocking the ?-carboxyl group of aspartic acid in peptide synthesis; the 1-adamantyl ester is prepared using DCC-DMAP: J. Chem. Soc., Perkin 1, 2129 (1988). See also Appendix 6.
• Thiol groups may also be protected by formation of the thioether in TFA. Cleavage is by means of Hg(II) salts: Chem. Pharm. Bull., 26, 1576 (1978).
• Reaction with Hydrogen fluoride pyridine complex, L17117, gives 1-fluoroadamantane, a general method for conversion of sec- and tert-alcohols to fluoroalkanes: Org. Synth. Coll., 6, 628 (1988).