[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl 4-methylbenzene-1-sulfonate

• ChemBase ID: 167130
• Molecular Formular: C21H20Cl2N2O5S
• Molecular Mass: 483.3649
• Monoisotopic Mass: 482.04699811
• SMILES: c1cc(cc(c1C1(OCC(O1)COS(=O)(=O)c1ccc(cc1)C)Cn1cncc1)Cl)Cl
• Canonical SMILES: Cc1ccc(cc1)S(=O)(=O)OCC1COC(O1)(Cn1ccnc1)c1ccc(cc1Cl)Cl
• InChI: InChI=1S/C21H20Cl2N2O5S/c1-15-2-5-18(6-3-15)31(26,27)29-12-17-11-28-21(30-17,13-25-9-8-24-14-25)19-7-4-16(22)10-20(19)23/h2-10,14,17H,11-13H2,1H3
• InChIKey: WAXNIYHZFWRPGS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl 4-methylbenzene-1-sulfonate; [2-(2,4-dichlorophenyl)-2-[(1H-imidazol-1-yl)methyl]-1,3-dioxolan-4-yl]methyl 4-methylbenzene-1-sulfonate
• IUPAC Traditional name: [2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl 4-methylbenzenesulfonate
• Synonyms: (2R,4R)-rel-2-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolane-4-methanol 4-(4-Methylbenzenesulfonate); cis-[2-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl p-Tolylsulfonate; cis-(2-(2,4-dichlorophenyl)-2-(1h-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl)methyl-4-methylbenzenesulphonate

Database IDs

• CAS Number: 134071-44-6
• PubChem SID: 162261263
• PubChem CID: 10390553

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 4.711972
• LogD (pH = 7.4): 5.1765785
• Log P: 5.2395
• Molar Refractivity: 117.0001 cm^3
• Polarizability: 46.560226 Å^3
• Polar Surface Area: 79.65 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White Solid
• Melting Point: 120-122°C

Safety Information

• Storage Condition: -20°C Freezer

Product Information

• Purity: 97%

DETAILS

Toronto Research Chemicals - D435718

An intermediate in the synthesis of the drug Ketoconazole (K186000).

REFERENCES

• McManus, O., et al.: Biochemistry, 32, 6128 (1993)
• Olesen, S., et al.: Eur. J. Pharmacol., 251, 53 (1993)
• Assano, M., et al.: J. Pharm. Exp. Ther., 275, 775 (1993)
• Hewawasam, P., et al.: J. Med. Chem., 45, 1487 (1993)