(S)-(6-methoxyquinolin-4-yl)[(2R,4S)-5-oxo-1-azabicyclo[2.2.2]octan-2-yl]methyl acetate

• ChemBase ID: 159051
• Molecular Formular: C20H22N2O4
• Molecular Mass: 354.39968
• Monoisotopic Mass: 354.15795719
• SMILES: c1(ccc2c(c1)c(ccn2)[C@@H]([C@@H]1N2CC[C@@H](C1)C(=O)C2)OC(=O)C)OC
• Canonical SMILES: COc1ccc2c(c1)c(ccn2)[C@@H]([C@H]1C[C@@H]2CCN1CC2=O)OC(=O)C
• InChI: InChI=1S/C20H22N2O4/c1-12(23)26-20(18-9-13-6-8-22(18)11-19(13)24)15-5-7-21-17-4-3-14(25-2)10-16(15)17/h3-5,7,10,13,18,20H,6,8-9,11H2,1-2H3/t13-,18+,20-/m0/s1
• InChIKey: JYRRDLVMUWTZKM-VIZZQPHQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (S)-(6-methoxyquinolin-4-yl)[(2R,4S)-5-oxo-1-azabicyclo[2.2.2]octan-2-yl]methyl acetate
• IUPAC Traditional name: (S)-(6-methoxyquinolin-4-yl)[(1S,2R,4S)-5-oxo-1-azabicyclo[2.2.2]octan-2-yl]methyl acetate
• Synonyms: (9S)-9-(Acetyloxy)-6'-methoxy-10,11-dinorcinchonan-3-one; (8R,9S)-6-Methoxy-3-oxo-9-rubanol Acetate; (8R, 9S)-6'-Methoxy-3-oxoruban-9-yl Acetate; 6'-Methoxy-3-oxo-9-rubanol Acetate; ICQ 9; 9-Acetoxy Rubanone

Database IDs

• CAS Number: 60723-43-5
• PubChem SID: 162253186
• PubChem CID: 10861157

CALCULATED PROPERTIES

• Acid pKa: 18.178755
• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 1.7798647
• LogD (pH = 7.4): 1.8877139
• Log P: 1.8892487
• Molar Refractivity: 95.1433 cm^3
• Polarizability: 38.77209 Å^3
• Polar Surface Area: 68.73 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: WHite Solid
• Melting Point: 162-163°C

DETAILS

Toronto Research Chemicals - A167700

An intermediate for the preparation of (3S)-3-Hydroxy Quinidine.

REFERENCES

• Carrol, F.I., et al.: J. CHem. Soc. Perkin Trans. 1, 12, 3017 (1991).