9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-yl 2-hydroxy-2,2-bis(thiophen-2-yl)acetate

• ChemBase ID: 177716
• Molecular Formular: C18H19NO4S2
• Molecular Mass: 377.47776
• Monoisotopic Mass: 377.07555009
• SMILES: C12C3C(C(N1C)CC(C2)OC(=O)C(c1cccs1)(c1sccc1)O)O3
• Canonical SMILES: CN1C2CC(CC1C1C2O1)OC(=O)C(c1cccs1)(c1cccs1)O
• InChI: InChI=1S/C18H19NO4S2/c1-19-11-8-10(9-12(19)16-15(11)23-16)22-17(20)18(21,13-4-2-6-24-13)14-5-3-7-25-14/h2-7,10-12,15-16,21H,8-9H2,1H3
• InChIKey: VPJFFOQGKSJBAY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 9-methyl-3-oxa-9-azatricyclo[3.3.1.0^2,^4]nonan-7-yl 2-hydroxy-2,2-bis(thiophen-2-yl)acetate
• IUPAC Traditional name: 9-methyl-3-oxa-9-azatricyclo[3.3.1.0^2,^4]nonan-7-yl 2-hydroxy-2,2-bis(thiophen-2-yl)acetate
• Synonyms: N-Demethyl Tiotropium; α-Hydroxy-α-2-thienyl-2-thiopheneacetic Acid (1α,2β,4β,5α,7β)-9-Methyl-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-yl Ester; Scopine Di(2-thienylglycolate)

Database IDs

• CAS Number: 136310-64-0
• PubChem SID: 164233626
• PubChem CID: 23553456

CALCULATED PROPERTIES

• Acid pKa: 10.35137
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.94037557
• LogD (pH = 7.4): 2.271813
• Log P: 2.405053
• Molar Refractivity: 93.2684 cm^3
• Polarizability: 37.141212 Å^3
• Polar Surface Area: 62.3 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White Solid
• Melting Point: 138-140°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - S199965

Precursor to Tiotropium Bromide.

REFERENCES

• Buchwald, P., et al.: Pharmazie., 55, S210 (2000)