(1S,2R)-2-(2,2-dichloroacetamido)-3-hydroxy-1-(4-nitrophenyl)propyl acetate

• ChemBase ID: 164057
• Molecular Formular: C13H14Cl2N2O6
• Molecular Mass: 365.16606
• Monoisotopic Mass: 364.02289154
• SMILES: c1c(ccc(c1)[C@@H]([C@@H](CO)NC(=O)C(Cl)Cl)OC(=O)C)[N+](=O)[O-]
• Canonical SMILES: OC[C@H]([C@H](c1ccc(cc1)[N+](=O)[O-])OC(=O)C)NC(=O)C(Cl)Cl
• InChI: InChI=1S/C13H14Cl2N2O6/c1-7(19)23-11(10(6-18)16-13(20)12(14)15)8-2-4-9(5-3-8)17(21)22/h2-5,10-12,18H,6H2,1H3,(H,16,20)/t10-,11+/m1/s1
• InChIKey: WEYAPUCXWINQDH-MNOVXSKESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R)-2-(2,2-dichloroacetamido)-3-hydroxy-1-(4-nitrophenyl)propyl acetate
• IUPAC Traditional name: (1S,2R)-2-(2,2-dichloroacetamido)-3-hydroxy-1-(4-nitrophenyl)propyl acetate
• Synonyms: N-[(1R,2R)-2-(Acetyloxy)-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]-2,2-dichloro-acetamide; 1-Acetoxychloramphenicol; 1-Acetylchloramphenicol; 1-O-Acetylchloramphenicol; Chloramphenicol 1-Acetate; Chloramphenicol 1'-Acetate; Chloramphenicol 1-Acetate

Database IDs

• CAS Number: 23214-93-9
• PubChem SID: 162258192
• PubChem CID: 71314672

CALCULATED PROPERTIES

• Acid pKa: 7.586428
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.3166898
• LogD (pH = 7.4): 1.1331861
• Log P: 1.3198289
• Molar Refractivity: 82.3522 cm^3
• Polarizability: 31.6734 Å^3
• Polar Surface Area: 121.45 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: White Solid

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C325090

Found in the metabolic decomposition of Chloramphenicol by Alcaligenes faecalis. A Chloramphenicol (C325030) derivative.

REFERENCES

• Obojska, K. et al.: Microbiologia Generalis 3, 63 (1971)