(8aS,12aS)-dodecahydro-4,5,1,8-benzodithiadiazecine-2,7-dione

• ChemBase ID: 162342
• Molecular Formular: C10H16N2O2S2
• Molecular Mass: 260.37624
• Monoisotopic Mass: 260.06531976
• SMILES: C1C[C@H]2[C@H](CC1)NC(=O)CSSCC(=O)N2
• Canonical SMILES: O=C1CSSCC(=O)N[C@@H]2[C@@H](N1)CCCC2
• InChI: InChI=1S/C10H16N2O2S2/c13-9-5-15-16-6-10(14)12-8-4-2-1-3-7(8)11-9/h7-8H,1-6H2,(H,11,13)(H,12,14)/t7-,8-/m0/s1
• InChIKey: UFOZXAMKSNONAJ-YUMQZZPRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (8aS,12aS)-dodecahydro-4,5,1,8-benzodithiadiazecine-2,7-dione
• IUPAC Traditional name: (8aS,12aS)-decahydro-4,5,1,8-benzodithiadiazecine-2,7-dione
• Synonyms: rel-N,N'-(1R,2R)-1,2-Cyclohexanediylbis[2-mercapto-acetamide; Vectrase P; BMC; (+/-)-trans-1,2-Bis(2-mercaptoacetamido)cyclohexane

Database IDs

• CAS Number: 257641-01-3
• PubChem SID: 162256477
• PubChem CID: 29974327

CALCULATED PROPERTIES

• Acid pKa: 13.681833
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 0.22768778
• LogD (pH = 7.4): 0.22768757
• Log P: 0.22768778
• Molar Refractivity: 66.7018 cm^3
• Polarizability: 26.322943 Å^3
• Polar Surface Area: 58.2 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White to Off-White Solid
• Melting Point: 193-194°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - B481450

A useful synthetic intermediate. BMC was particularly effective in refolding disulfide-containing proteins.

REFERENCES

• Willis, M.S., et al.: Protein Sci., 14, 7, 1818 (2005)
• Fink, M., et al.: Biophys. Chem., 132, 104 (2005)