4-{[(tert-butoxy)carbonyl]amino}-1-[(9H-fluoren-9-ylmethoxy)carbonyl]piperidine-4-carboxylic acid

• ChemBase ID: 162511
• Molecular Formular: C26H30N2O6
• Molecular Mass: 466.5262
• Monoisotopic Mass: 466.21038669
• SMILES: C1CC(CCN1C(=O)OCC1c2c(c3c1cccc3)cccc2)(NC(=O)OC(C)(C)C)C(=O)O
• Canonical SMILES: O=C(NC1(CCN(CC1)C(=O)OCC1c2ccccc2c2c1cccc2)C(=O)O)OC(C)(C)C
• InChI: InChI=1S/C26H30N2O6/c1-25(2,3)34-23(31)27-26(22(29)30)12-14-28(15-13-26)24(32)33-16-21-19-10-6-4-8-17(19)18-9-5-7-11-20(18)21/h4-11,21H,12-16H2,1-3H3,(H,27,31)(H,29,30)
• InChIKey: SHJZHFAOEGNFGY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{[(tert-butoxy)carbonyl]amino}-1-[(9H-fluoren-9-ylmethoxy)carbonyl]piperidine-4-carboxylic acid; 4-{[(tert-butoxy)carbonyl]amino}-1-{[(9H-fluoren-9-yl)methoxy]carbonyl}piperidine-4-carboxylic acid
• IUPAC Traditional name: 4-[(tert-butoxycarbonyl)amino]-1-[(9H-fluoren-9-ylmethoxy)carbonyl]piperidine-4-carboxylic acid
• Synonyms: 4-[[(1,1-Dimethylethoxy)carbonyl]amino]-1,4-piperidinedicarboxylic Acid 1-(9H-Fluoren-9-ylmethyl) Ester; 4-[(tert-Butoxycarbonyl)amino]-1-[[(9H-fluoren-9-yl)methoxy]carbonyl]piperidine-4-carboxylic Acid; 4-(Boc-amino)-1-(Fmoc-piperidinyl)-4-carboxylic Acid; 4-(BOC-AMINO)-1-FMOC-PIPERIDINE-4-CARBOXYLIC ACID

Database IDs

• CAS Number: 368866-07-3
• PubChem SID: 162256646
• PubChem CID: 2734589

CALCULATED PROPERTIES

• Acid pKa: 3.6531768
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.7876182
• LogD (pH = 7.4): 0.30791605
• Log P: 3.6316512
• Molar Refractivity: 125.2745 cm^3
• Polarizability: 49.90869 Å^3
• Polar Surface Area: 105.17 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Product Information

• Purity: 98%

DETAILS

Toronto Research Chemicals - B619260

4-(Boc-amino)-1-(Fmoc-piperidinyl)-4-carboxylic acid is used in the preparation of synthetic peptide amides as kappa opioid receptor agonists for treatment of pain, pruritis and inflammation associated with a variety of diseases.

REFERENCES

• Ghosh, S., et al.: J. Med. Chem., 49, 2669 (2006)