2-azabicyclo[2.2.1]hept-5-en-3-one

• ChemBase ID: 68046
• Molecular Formular: C6H7NO
• Molecular Mass: 109.12588
• Monoisotopic Mass: 109.05276385
• SMILES: C12NC(=O)C(C=C1)C2
• Canonical SMILES: C1C2C=CC1NC2=O
• InChI: InChI=1S/C6H7NO/c8-6-4-1-2-5(3-4)7-6/h1-2,4-5H,3H2,(H,7,8)
• InChIKey: DDUFYKNOXPZZIW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-azabicyclo[2.2.1]hept-5-en-3-one
• IUPAC Traditional name: 2-azabicyclo[2.2.1]hept-5-en-3-one
• Synonyms: 2-Azabicyclo[2.2.1]hept-5-en-3-one; (+/-)-2-Azabicyclo[2.2.1]hept-5-en-3-one; (+/-)-Vince Lactam; Vince Lactam; rac 2-Azabicyclo[2.2.1]hept-5-en-3-one

Database IDs

• CAS Number: 49805-30-3
• MDL Number: MFCD00213364
• PubChem SID: 162033778
• PubChem CID: 548678

CALCULATED PROPERTIES

• Acid pKa: 14.183221
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): -0.21183437
• LogD (pH = 7.4): -0.21183443
• Log P: -0.21183437
• Molar Refractivity: 30.3346 cm^3
• Polarizability: 11.299311 Å^3
• Polar Surface Area: 29.1 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 55-57°C

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: IRRITANT
• TSCA Listed: false

Product Information

• Purity: 95+%; 98%

DETAILS

Toronto Research Chemicals - A795200

Abacavir intermediate. Used as an intermediate in the synthesis of carbocyclic sugar amines, carbanucleosides, and carbocyclic dinucleotide analogues.

REFERENCES

• Kam, B.L. et al.: J. Org. Chem., 46, 3268 (1981)
• Slama, J.T., et al.: Biochemistry, 27, 183 (1981)