benzyl (2S)-4-oxoazetidine-2-carboxylate

• ChemBase ID: 150030
• Molecular Formular: C11H11NO3
• Molecular Mass: 205.20994
• Monoisotopic Mass: 205.07389322
• SMILES: c1ccc(cc1)COC(=O)[C@@H]1CC(=O)N1
• Canonical SMILES: O=C([C@@H]1CC(=O)N1)OCc1ccccc1
• InChI: InChI=1S/C11H11NO3/c13-10-6-9(12-10)11(14)15-7-8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H,12,13)/t9-/m0/s1
• InChIKey: WGLLBHSIXLWVFU-VIFPVBQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl (2S)-4-oxoazetidine-2-carboxylate
• IUPAC Traditional name: benzyl (2S)-4-oxoazetidine-2-carboxylate
• Synonyms: Benzyl (S)-(-)-4-oxo-2-azetidinecarboxylate; (S)-4-氧代-2-氮杂环丁烷羧酸苄酯

Database IDs

• CAS Number: 72776-05-7
• MDL Number: MFCD00798164
• PubChem SID: 162244192; 24870544
• PubChem CID: 717310

CALCULATED PROPERTIES

• Rotatable Bonds: 4
• Lipinski's Rule of Five: true
• Acid pKa: 10.929173
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.69203484
• LogD (pH = 7.4): 0.6919225
• Log P: 0.6920363
• Molar Refractivity: 52.7145 cm^3
• Polarizability: 20.800291 Å^3
• Polar Surface Area: 55.4 Å^2

PROPERTIES

Physical Property

• Melting Point: 137-140 °C(lit.)
• Optical Rotation: [α]21/D -44°, c = 3.3 in chloroform

Safety Information

• German water hazard class: 3

Product Information

• Purity: 97%
• Empirical Formula (Hill Notation): C11H11NO3

DETAILS

Sigma Aldrich - 468975

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
Packaging
5 g in glass bottle