tert-butyl (3aS,7aR)-5-oxo-octahydro-1H-indole-1-carboxylate

• ChemBase ID: 162627
• Molecular Formular: C13H21NO3
• Molecular Mass: 239.31074
• Monoisotopic Mass: 239.15214354
• SMILES: C1(=O)CC[C@@H]2[C@H](C1)CCN2C(=O)OC(C)(C)C
• Canonical SMILES: O=C1CC[C@@H]2[C@H](C1)CCN2C(=O)OC(C)(C)C
• InChI: InChI=1S/C13H21NO3/c1-13(2,3)17-12(16)14-7-6-9-8-10(15)4-5-11(9)14/h9,11H,4-8H2,1-3H3/t9-,11+/m0/s1
• InChIKey: FAFPNFIAMGOSNB-GXSJLCMTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl (3aS,7aR)-5-oxo-octahydro-1H-indole-1-carboxylate
• IUPAC Traditional name: tert-butyl (3aS,7aR)-5-oxo-hexahydro-2H-indole-1-carboxylate
• Synonyms: (3aR,7aS)-rel-Octahydro-5-oxo-1H-indole-1-carboxylic Acid 1,1-Dimethylethyl Ester; cis-(±)-Octahydro-5-oxo-1H-indole-1-carboxylic Acid 1,1-Dimethylethyl Ester; cis-rac-N-Boc-5-oxooctahydro-1H-indole

Database IDs

• CAS Number: 143268-07-9
• PubChem SID: 162256762
• PubChem CID: 10399347

CALCULATED PROPERTIES

• Lipinski's Rule of Five: true
• Acid pKa: 19.29565
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.6018074
• LogD (pH = 7.4): 1.6018074
• Log P: 1.6018074
• Molar Refractivity: 64.0841 cm^3
• Polarizability: 25.213781 Å^3
• Polar Surface Area: 46.61 Å^2
• Rotatable Bonds: 2

DETAILS

Toronto Research Chemicals - B661180

An intermediate in the synthesis of a series of analogs of Manzamine A, an antimalarial agent.

REFERENCES

• Ang, K., et al.: Antimicrob. Agents Chemother., 44, 1645 (2000)
• Bell, A., et al.: Drugs, 3, 310 (2000)
• Marshall, E., et al.: Science, 290, 428 (2000)