(2S)-4-oxoazetidine-2-carboxylic acid

• ChemBase ID: 148307
• Molecular Formular: C4H5NO3
• Molecular Mass: 115.0874
• Monoisotopic Mass: 115.02694303
• SMILES: C1[C@H](NC1=O)C(=O)O
• Canonical SMILES: O=C1C[C@H](N1)C(=O)O
• InChI: InChI=1S/C4H5NO3/c6-3-1-2(5-3)4(7)8/h2H,1H2,(H,5,6)(H,7,8)/t2-/m0/s1
• InChIKey: YSPMLLKKKHCTBN-REOHCLBHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-4-oxoazetidine-2-carboxylic acid
• IUPAC Traditional name: (2S)-4-oxoazetidine-2-carboxylic acid
• Synonyms: (S)-(-)-4-Oxo-2-azetidinecarboxylic acid; (S)-(-)-4-氧代-2-吖丁啶羧酸

Database IDs

• CAS Number: 16404-94-7
• MDL Number: MFCD00799571
• PubChem SID: 162242483; 24870891
• PubChem CID: 13469007

CALCULATED PROPERTIES

• Acid pKa: 3.4079607
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -3.25829
• LogD (pH = 7.4): -4.5792174
• Log P: -1.1783309
• Molar Refractivity: 23.3328 cm^3
• Polarizability: 9.3078575 Å^3
• Polar Surface Area: 66.4 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 99-102 °C(lit.)
• Optical Rotation: [α]20/D -46°, c = 1 in methanol

Safety Information

• German water hazard class: 3

Product Information

• Purity: 98%
• Empirical Formula (Hill Notation): C4H5NO3

DETAILS

Sigma Aldrich - 473278

Packaging
1 g in glass bottle
Application
Important building block for the synthesis of NMDA receptor antagonists,1 3-alkyl-L-aspartic acids,2 and orally active β-lactam inhibitors.3