1-({[2-(ethenesulfonyl)ethoxy]carbonyl}oxy)pyrrolidine-2,5-dione

• ChemBase ID: 163664
• Molecular Formular: C9H11NO7S
• Molecular Mass: 277.25114
• Monoisotopic Mass: 277.0256227
• SMILES: O(C(=O)OCCS(=O)(=O)C=C)N1C(=O)CCC1=O
• Canonical SMILES: C=CS(=O)(=O)CCOC(=O)ON1C(=O)CCC1=O
• InChI: InChI=1S/C9H11NO7S/c1-2-18(14,15)6-5-16-9(13)17-10-7(11)3-4-8(10)12/h2H,1,3-6H2
• InChIKey: SJPUQNFPDYCHBX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-({[2-(ethenesulfonyl)ethoxy]carbonyl}oxy)pyrrolidine-2,5-dione
• IUPAC Traditional name: 1-({[2-(ethenesulfonyl)ethoxy]carbonyl}oxy)pyrrolidine-2,5-dione
• Synonyms: Carbonic Acid 2,5-Dioxo-1-pyrrolidinyl 2-(Ethenylsulfonyl)ethyl Ester; [[2-(Ethenylsulfonyl)ethoxy]carbonyl]oxy]-2,5-pyrrolidinedione; Succinimidyl 2-(Vinylsulfonyl)ethyl Carbonate; SVEC; Carbonic Acid 2,5-Dioxo-1-pyrrolidinyl 2-(Ethenylsulfonyl)ethyl Ester

Database IDs

• CAS Number: 918822-70-5
• PubChem SID: 162257799
• PubChem CID: 16095500

CALCULATED PROPERTIES

• Acid pKa: 17.634207
• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): -0.82242876
• LogD (pH = 7.4): -0.82242876
• Log P: -0.82242876
• Molar Refractivity: 56.4251 cm^3
• Polarizability: 23.603403 Å^3
• Polar Surface Area: 107.05 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C176635

A cleavable amino-thiol cross-linker used for reversible linking of amines to thiol-modified DNA

REFERENCES

• Hojfeldt, J.W. et al.: J. Org. Chem., 71, 9556 (2006)