bicyclo[2.2.2]octa-2,5-diene-2-carboxylic acid

• ChemBase ID: 162048
• Molecular Formular: C9H10O2
• Molecular Mass: 150.1745
• Monoisotopic Mass: 150.06807956
• SMILES: C1CC2C=C(C1C=C2)C(=O)O
• Canonical SMILES: OC(=O)C1=CC2CCC1C=C2
• InChI: InChI=1S/C9H10O2/c10-9(11)8-5-6-1-3-7(8)4-2-6/h1,3,5-7H,2,4H2,(H,10,11)
• InChIKey: KHKYIHFNQHBFAM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: bicyclo[2.2.2]octa-2,5-diene-2-carboxylic acid
• IUPAC Traditional name: bicyclo[2.2.2]octa-2,5-diene-2-carboxylic acid
• Synonyms: Bicyclo[2.2.2]octa-2,5-diene-2-carboxylic Acid

Database IDs

• CAS Number: 102589-30-0
• PubChem SID: 162256183
• PubChem CID: 14423377

CALCULATED PROPERTIES

• Acid pKa: 4.679769
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.6083719
• LogD (pH = 7.4): -1.1694826
• Log P: 1.4889349
• Molar Refractivity: 43.1334 cm^3
• Polarizability: 15.881185 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Methanol
• Apperance: Off-White to Light Tan Solid
• Melting Point: 91-93°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - B382850

Intermediate in the production of Prazosin and Prazosin analogs.

REFERENCES

• Pitha, J., et al.: J. Med. Chem., 32, 96 (1989)
• Donkor, I., et al.: Eur. J. Med. Chem., 34, 235 (1989)