(2R,4S)-4-cyclohexylpyrrolidine-2-carboxylic acid hydrochloride

• ChemBase ID: 165218
• Molecular Formular: C11H20ClNO2
• Molecular Mass: 233.735
• Monoisotopic Mass: 233.11825657
• SMILES: C1[C@H](CN[C@H]1C(=O)O)C1CCCCC1.Cl
• Canonical SMILES: OC(=O)[C@@H]1NC[C@@H](C1)C1CCCCC1.Cl
• InChI: InChI=1S/C11H19NO2.ClH/c13-11(14)10-6-9(7-12-10)8-4-2-1-3-5-8;/h8-10,12H,1-7H2,(H,13,14);1H/t9-,10-;/m1./s1
• InChIKey: BHGFUQJUTOVQOS-DHTOPLTISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4S)-4-cyclohexylpyrrolidine-2-carboxylic acid hydrochloride
• IUPAC Traditional name: (2R,4S)-4-cyclohexylpyrrolidine-2-carboxylic acid hydrochloride
• Synonyms: trans-4-Cyclohexyl-L-proline Hydrochloride; (4S)-4-Cyclohexyl-L-proline Hydrochloride

Database IDs

• CAS Number: 90657-55-9
• PubChem SID: 162259351
• PubChem CID: 71315086

CALCULATED PROPERTIES

• Acid pKa: 2.2146025
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.6022594
• LogD (pH = 7.4): -0.602108
• Log P: -0.6020914
• Molar Refractivity: 53.6863 cm^3
• Polarizability: 21.574009 Å^3
• Polar Surface Area: 49.33 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 177-180°C

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - C988110

It is an intermediate for the synthesis of angiotensin-converting enzyme inhibitors, e.g. Fosinopril (F727800).

REFERENCES

• Renaud, P., et al.: Helv. Chim. Acta, 69, 1704 (1986)
• Thaisrivongs, S., et al.: J. Med. Chem., 31, 1369 (1986)