4-amino-1-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid

• ChemBase ID: 16383
• Molecular Formular: C11H20N2O4
• Molecular Mass: 244.2875
• Monoisotopic Mass: 244.14230713
• SMILES: N1(CCC(CC1)(N)C(=O)O)C(=O)OC(C)(C)C
• Canonical SMILES: O=C(N1CCC(CC1)(N)C(=O)O)OC(C)(C)C
• InChI: InChI=1S/C11H20N2O4/c1-10(2,3)17-9(16)13-6-4-11(12,5-7-13)8(14)15/h4-7,12H2,1-3H3,(H,14,15)
• InChIKey: YNHLVALLAURVJF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-1-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid
• IUPAC Traditional name: 4-amino-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid
• Synonyms: 4-Amino-1,4-piperidinedicarboxylic Acid 1-(1,1-Dimethylethyl) Ester; 1-(tert-Butyloxycarbonyl)-4-aminopiperidine-4-carboxylic acid; 4-Aminopiperidine-1,4-dicarboxylic Acid Mono-tert-butyl Ester; 1-Boc-4-aminopiperidine-4-carboxylic Acid; 4-Amino-1-Boc-piperidine-4-carboxylic acid; 4-Amino-1-Boc-piperidine-4-carboxylic acid; 4-Amino-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid; 1-Boc-4-aminopiperidine-4-carboxylic acid; 4-Amino-1-Boc-piperidine-4-carboxylic acid; 4-氨基-1-(叔丁氧羰基)哌啶-4-羧酸; 4-氨基-1-Boc-哌啶-4-羧酸; 1-Boc-4-氨基哌啶-4-羧酸; 4-氨基-1Boc-哌啶-4-羧酸

Database IDs

• CAS Number: 183673-71-4
• EC Number: 000-000-0
• MDL Number: MFCD01318728
• Beilstein Number: 7588844
• PubChem SID: 160979690
• PubChem CID: 693797

CALCULATED PROPERTIES

• Acid pKa: 2.2594976
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -2.2546482
• LogD (pH = 7.4): -2.2589772
• Log P: -2.2546322
• Molar Refractivity: 61.1947 cm^3
• Polarizability: 24.284832 Å^3
• Polar Surface Area: 92.86 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid
• Melting Point: >265°C (Dec.); 289-294 °C; ca 290°C dec.

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3
• TSCA Listed: false; 否

Product Information

• Purity: 97%; 98%
• Empirical Formula (Hill Notation): C11H20N2O4

DETAILS

Sigma Aldrich - 680095

Packaging
500 mg in glass bottle
Application
Involved in investigations of conformational effects on electron-transfer efficientcy in peptide foldamers1Reactant for synthesis of:
• SIRT2 inhibitors2
• Melanin-concentrating hormone receptor 1 antagonists3
• Bradykinin hB2 receptor antagonists4
• Neurokinin-1 receptor ligands5

Toronto Research Chemicals - B621125

An α,α-Disubstituted amino acid for preparation of water-soluble highly helical peptides.

REFERENCES

• Mak, J., et al.: Eur. J. Pharmacol., 194, 37 (1991)
• Fattori, D., et al.: J. Med. Chem., 49, 3602 (1991)