(1S,2R,5R)-3-[(tert-butoxy)carbonyl]-3-azabicyclo[3.1.0]hexane-2-carboxylic acid

• ChemBase ID: 162608
• Molecular Formular: C11H17NO4
• Molecular Mass: 227.25698
• Monoisotopic Mass: 227.11575803
• SMILES: [C@@H]12[C@@H]([C@@H](N(C1)C(=O)OC(C)(C)C)C(=O)O)C2
• Canonical SMILES: OC(=O)[C@H]1[C@H]2C[C@H]2CN1C(=O)OC(C)(C)C
• InChI: InChI=1S/C11H17NO4/c1-11(2,3)16-10(15)12-5-6-4-7(6)8(12)9(13)14/h6-8H,4-5H2,1-3H3,(H,13,14)/t6-,7-,8+/m0/s1
• InChIKey: RTWMQNSZCUYSJJ-BIIVOSGPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5R)-3-[(tert-butoxy)carbonyl]-3-azabicyclo[3.1.0]hexane-2-carboxylic acid
• IUPAC Traditional name: (1S,2R,5R)-3-(tert-butoxycarbonyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid
• Synonyms: (1S,2R,5R)-3-Azabicyclo[3.1.0]hexane-2,3-dicarboxylic Acid 3-(1,1-Dimethylethyl) Ester; N-Boc-cis-3,4-methylene D-Proline

Database IDs

• CAS Number: 937244-10-5
• PubChem SID: 162256743
• PubChem CID: 49760041

CALCULATED PROPERTIES

• Acid pKa: 3.8976936
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.60021555
• LogD (pH = 7.4): -2.2070785
• Log P: 1.0077027
• Molar Refractivity: 55.5994 cm^3
• Polarizability: 22.048151 Å^3
• Polar Surface Area: 66.84 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B656985

Used in the pyrrolidine carboxamides preparation and SAR as 11β-HSD1 inhibitors.

REFERENCES

• Davani, B., et al.: J. Biol. Chem., 275, 34841 (2000)
• Kershaw, E., et al.: Diabetes, 54, 1023 (2000)
• Patel, J., et al.: Bioorg. Med. Chem. Lett., 17, 750 (2000)