benzyl (2R)-2-(hydroxymethyl)piperidine-1-carboxylate

• ChemBase ID: 161783
• Molecular Formular: C14H19NO3
• Molecular Mass: 249.30556
• Monoisotopic Mass: 249.13649347
• SMILES: C1CCCN([C@H]1CO)C(=O)OCc1ccccc1
• Canonical SMILES: OC[C@H]1CCCCN1C(=O)OCc1ccccc1
• InChI: InChI=1S/C14H19NO3/c16-10-13-8-4-5-9-15(13)14(17)18-11-12-6-2-1-3-7-12/h1-3,6-7,13,16H,4-5,8-11H2/t13-/m1/s1
• InChIKey: UDGDHNGWPNSYCD-CYBMUJFWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl (2R)-2-(hydroxymethyl)piperidine-1-carboxylate
• IUPAC Traditional name: benzyl (2R)-2-(hydroxymethyl)piperidine-1-carboxylate
• Synonyms: (2R)-2-(Hydroxymethyl)-1-piperidinecarboxylic Acid Phenylmethyl Ester; (+)-2-(Hydroxymethyl)-1-piperidinecarboxylic Acid Phenylmethyl Ester; (R)-N-Benzyloxycarbonyl-2-piperidinemethanol

Database IDs

• CAS Number: 154499-13-5
• PubChem SID: 162255918
• PubChem CID: 11128697

CALCULATED PROPERTIES

• Acid pKa: 15.090304
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.9808593
• LogD (pH = 7.4): 1.9808593
• Log P: 1.9808593
• Molar Refractivity: 68.6 cm^3
• Polarizability: 26.851816 Å^3
• Polar Surface Area: 49.77 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate
• Apperance: Colourless Oil

DETAILS

Toronto Research Chemicals - B286330

Intermediate for the preparation of 1-hydroxyalkyl-3-phenylthioureas as HDL- and Apo A-I-elevating agents.

REFERENCES

• Coppola, G., Bioorg. Med. Chem. Lett., 12, 2439 (2002)
• Coppola, G., et al.: Bioorg. Med. Chem. Lett., 15, 809 (2005).