ethyl (1S,5R,6S)-3-benzyl-2,4-dioxo-3-azabicyclo[3.1.0]hexane-6-carboxylate

• ChemBase ID: 51345
• Molecular Formular: C15H15NO4
• Molecular Mass: 273.2839
• Monoisotopic Mass: 273.10010797
• SMILES: N1(C(=O)[C@@H]2[C@H](C1=O)[C@H]2C(=O)OCC)Cc1ccccc1
• Canonical SMILES: CCOC(=O)[C@@H]1[C@@H]2[C@H]1C(=O)N(C2=O)Cc1ccccc1
• InChI: InChI=1S/C15H15NO4/c1-2-20-15(19)12-10-11(12)14(18)16(13(10)17)8-9-6-4-3-5-7-9/h3-7,10-12H,2,8H2,1H3/t10-,11+,12+
• InChIKey: SFFQYGDIFWFUAF-GDNZZTSVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (1S,5R,6S)-3-benzyl-2,4-dioxo-3-azabicyclo[3.1.0]hexane-6-carboxylate; ethyl (1R,5S,6R)-3-benzyl-2,4-dioxo-3-azabicyclo[3.1.0]hexane-6-carboxylate
• IUPAC Traditional name: ethyl (1S,5R,6S)-3-benzyl-2,4-dioxo-3-azabicyclo[3.1.0]hexane-6-carboxylate; ethyl (1R,5S,6R)-3-benzyl-2,4-dioxo-3-azabicyclo[3.1.0]hexane-6-carboxylate
• Synonyms: ethyl (1 alpha,5 alpha,6 alpha)-3-benzyl-3-azabicyclo[3.1.0]hexane-2,4-dione-6-carboxylate; Ethyl (1S,5R,6R)-3-benzyl-2,4-dioxo-3-azabicyclo-[3.1.0]hexane-6-carboxylate

Database IDs

• CAS Number: 134575-06-7
• MDL Number: MFCD16140349; MFCD16170316
• PubChem SID: 162056108
• PubChem CID: 11033026

CALCULATED PROPERTIES

• Acid pKa: 16.4046
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.85780215
• LogD (pH = 7.4): 0.85780215
• Log P: 0.85780215
• Molar Refractivity: 70.2941 cm^3
• Polarizability: 27.529633 Å^3
• Polar Surface Area: 63.68 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 99 - 100 °C; 99-100°C

Safety Information

• Storage Warning: IRRITANT
• TSCA Listed: false

Product Information

• Purity: >95%