8-(propan-2-yl)-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate

• ChemBase ID: 171936
• Molecular Formular: C19H27NO3
• Molecular Mass: 317.42258
• Monoisotopic Mass: 317.19909373
• SMILES: C(CO)(C(=O)OC1CC2CCC(N2C(C)C)C1)c1ccccc1
• Canonical SMILES: OCC(c1ccccc1)C(=O)OC1CC2CCC(C1)N2C(C)C
• InChI: InChI=1S/C19H27NO3/c1-13(2)20-15-8-9-16(20)11-17(10-15)23-19(22)18(12-21)14-6-4-3-5-7-14/h3-7,13,15-18,21H,8-12H2,1-2H3
• InChIKey: VORSMCHHJRVORT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 8-(propan-2-yl)-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate
• IUPAC Traditional name: 8-isopropyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate
• Synonyms: α-(Hydroxymethyl)benzeneacetic Acid (3-Endo)-8-(1-methylethyl)-8-azabicyclo[3.2.1]-oct-3-yl Ester; α-(Hydroxymethyl)benzeneacetic Acid endo-8-(1-Methylethyl)-8-azabicyclo[3.2.1]oct-3-yl Ester; N-Desmethyl Ipratropium; N-Isopropyl Noratropine

Database IDs

• CAS Number: 22235-81-0
• PubChem SID: 164227846
• PubChem CID: 20625249

CALCULATED PROPERTIES

• Acid pKa: 15.145742
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -1.109304
• LogD (pH = 7.4): -0.15041001
• Log P: 2.344624
• Molar Refractivity: 89.9838 cm^3
• Polarizability: 35.718067 Å^3
• Polar Surface Area: 49.77 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White to Pale Orange Solid
• Melting Point: 112-114°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - I872680

N-Isopropyl Noratropine is a Noratropine derivative, an intermediate in the production of Ipratropium.

REFERENCES

• Simms, P., et al.: J. Pharm. Biomed. Anal., 17, 841 (1998)