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

• ChemBase ID: 159142
• Molecular Formular: C22H26N2O3
• Molecular Mass: 366.45344
• Monoisotopic Mass: 366.1943427
• SMILES: c1(ccc2c(c1)c(ccn2)[C@@H]([C@@H]1N2CC[C@@H](C1)/C(=C/C)/C2)OC(=O)C)OC
• Canonical SMILES: C/C=C/1\CN2CC[C@H]1C[C@@H]2[C@H](c1ccnc2c1cc(OC)cc2)OC(=O)C
• InChI: InChI=1S/C22H26N2O3/c1-4-15-13-24-10-8-16(15)11-21(24)22(27-14(2)25)18-7-9-23-20-6-5-17(26-3)12-19(18)20/h4-7,9,12,16,21-22H,8,10-11,13H2,1-3H3/b15-4+/t16-,21+,22-/m0/s1
• InChIKey: UVUZUZKZOWNTJI-JJJURRGRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (S)-[(2R,4S,5Z)-5-ethylidene-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methyl acetate
• IUPAC Traditional name: (S)-[(1S,2R,4S,5Z)-5-ethylidene-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methyl acetate
• Synonyms: (9S)-3,10-Didehydro-10,11-dihydro-6'-methoxycinchonan-9-ol Acetate; 9-Acetyl Apoquinidine Methyl Ether

Database IDs

• CAS Number: 139239-49-9
• PubChem SID: 162253277
• PubChem CID: 11046784

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 0.71135813
• LogD (pH = 7.4): 2.436873
• Log P: 2.9309516
• Molar Refractivity: 104.574 cm^3
• Polarizability: 42.157692 Å^3
• Polar Surface Area: 51.66 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 102-107°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - A168410

A synthetic quinidine derivative.

REFERENCES

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