adamantan-2-one

• ChemBase ID: 69625
• Molecular Formular: C10H14O
• Molecular Mass: 150.21756
• Monoisotopic Mass: 150.10446507
• SMILES: C12C(=O)C3CC(CC(C1)C3)C2
• Canonical SMILES: O=C1C2CC3CC1CC(C2)C3
• InChI: InChI=1S/C10H14O/c11-10-8-2-6-1-7(4-8)5-9(10)3-6/h6-9H,1-5H2
• InChIKey: IYKFYARMMIESOX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: adamantan-2-one
• IUPAC Traditional name: @adamantanone; adamantanone
• Synonyms: Tricyclo[3.3.1.1~3,7~]decan-2-one; 2-Oxotricyclo[3.3.1.1~3,7~]decane; Adamantan-2-one 98%; 2-Adamantanone; 2-Adamantanone; adamantan-2-one; (1r,3r,5r,7r)-adamantan-2-one; 2-金刚烷酮

Database IDs

• CAS Number: 700-58-3
• EC Number: 211-847-2
• MDL Number: MFCD00074737
• Beilstein Number: 1210235
• PubChem SID: 162035351
• PubChem CID: 64151

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 2.2207532
• LogD (pH = 7.4): 2.2207532
• Log P: 2.2207532
• Molar Refractivity: 42.8892 cm^3
• Polarizability: 17.032516 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 257(subl.)°C; ca 257°C subl.

Safety Information

• Storage Warning: IRRITANT; Irritant
• RTECS: AU5018000
• TSCA Listed: false; 否

Product Information

• Purity: 95+%; 97%; 98%

REFERENCES

• Reductive coupling (TiCl₃/Li) gives (adamantylidene)adamantane, an example of a general method for the synthesis of highly-substituted alkenes: Org. Synth. Coll., 7, 1 (1990).
• Preparation of highly-substituted alkenes by the Wittig reaction gives poor yields with adamantanone. The route involving addition of a Grignard or alkyllithium reagent is to be preferred: J. Org. Chem., 54, 1375 (1989).