(6R,7R)-7-amino-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 160542
• Molecular Formular: C9H10N2O3S
• Molecular Mass: 226.2523
• Monoisotopic Mass: 226.04121319
• SMILES: [C@@H]12N(C(=C(CS1)C=C)C(=O)O)C(=O)[C@H]2N
• Canonical SMILES: C=CC1=C(C(=O)O)N2[C@H](SC1)[C@@H](C2=O)N
• InChI: InChI=1S/C9H10N2O3S/c1-2-4-3-15-8-5(10)7(12)11(8)6(4)9(13)14/h2,5,8H,1,3,10H2,(H,13,14)/t5-,8-/m1/s1
• InChIKey: GQLGFBRMCCVQLU-SVGQVSJJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-amino-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: (6R,7R)-7-amino-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• Synonyms: (6R,7R)-7-Amino-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; (6R-trans)-7-Amino-3-ethenyl-8-oxo-5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; 7-AVCA; 7-Amino-3-vinyl-3-cephem-4-carboxylic Acid

Database IDs

• CAS Number: 79349-82-9
• PubChem SID: 162254677
• PubChem CID: 7280824

CALCULATED PROPERTIES

• Acid pKa: 3.632503
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -2.828477
• LogD (pH = 7.4): -3.103844
• Log P: -2.8364108
• Molar Refractivity: 56.4573 cm^3
• Polarizability: 21.75603 Å^3
• Polar Surface Area: 83.63 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO (Sparingly)
• Apperance: White Solid
• Melting Point: 215-220°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A632600

A key intermediate in the manufacturing of Cephalosporin compounds.

REFERENCES

• Choi, K., et al.: J. Antibio., 50, 279 (1997)