4-[(1R,2R)-2-(2,2-dichloroacetamido)-1,3-dihydroxypropyl]benzene-1-sulfonyl chloride

• ChemBase ID: 164647
• Molecular Formular: C11H12Cl3NO5S
• Molecular Mass: 376.64068
• Monoisotopic Mass: 374.95017653
• SMILES: c1([C@H]([C@@H](CO)NC(=O)C(Cl)Cl)O)ccc(cc1)S(=O)(=O)Cl
• Canonical SMILES: OC[C@H]([C@@H](c1ccc(cc1)S(=O)(=O)Cl)O)NC(=O)C(Cl)Cl
• InChI: InChI=1S/C11H12Cl3NO5S/c12-10(13)11(18)15-8(5-16)9(17)6-1-3-7(4-2-6)21(14,19)20/h1-4,8-10,16-17H,5H2,(H,15,18)/t8-,9-/m1/s1
• InChIKey: KRVOZFMABPNKAD-RKDXNWHRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(1R,2R)-2-(2,2-dichloroacetamido)-1,3-dihydroxypropyl]benzene-1-sulfonyl chloride
• IUPAC Traditional name: 4-[(1R,2R)-2-(2,2-dichloroacetamido)-1,3-dihydroxypropyl]benzenesulfonyl chloride
• Synonyms: 4-[2-[(2,2-Dichloroacetyl)amino]-1,3-dihydroxypropyl]benzenesulfonyl Chloride; p-[2-(2,2-Dichloroacetamido)-1,3-dihydroxypropyl]benzenesulfonyl Chloride; D-threo-1-(4-Chlorosulfonylphenyl)-2-dichloroacetylamino-1,3-propanediol

Database IDs

• PubChem SID: 162258782
• PubChem CID: 71314817

CALCULATED PROPERTIES

• Acid pKa: 6.8943157
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 0.8698421
• LogD (pH = 7.4): 0.3966179
• Log P: 0.88502234
• Molar Refractivity: 80.0702 cm^3
• Polarizability: 32.04081 Å^3
• Polar Surface Area: 103.7 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane
• Melting Point: 128-129°C

DETAILS

Toronto Research Chemicals - C380050

An analogue of Chloramphenicol (C325030).

REFERENCES

• Shemyakin, M.M., et al.: J. Gen. Chem. U.S.S.R., 25, 1147 (1955)