[(2R,4R)-2-(bromomethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl]methyl benzoate

• ChemBase ID: 162971
• Molecular Formular: C18H15BrCl2O4
• Molecular Mass: 446.1193
• Monoisotopic Mass: 443.95307632
• SMILES: C1O[C@@](O[C@H]1COC(=O)c1ccccc1)(c1ccc(cc1Cl)Cl)CBr
• Canonical SMILES: BrC[C@@]1(OC[C@@H](O1)COC(=O)c1ccccc1)c1ccc(cc1Cl)Cl
• InChI: InChI=1S/C18H15BrCl2O4/c19-11-18(15-7-6-13(20)8-16(15)21)24-10-14(25-18)9-23-17(22)12-4-2-1-3-5-12/h1-8,14H,9-11H2/t14-,18-/m0/s1
• InChIKey: OXUPOIXSQGXRGF-KSSFIOAISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,4R)-2-(bromomethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl]methyl benzoate
• IUPAC Traditional name: [(2R,4R)-2-(bromomethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl]methyl benzoate
• Synonyms: (2R,4R)-rel-2-(Bromomethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolane-4-methanol Benzoate; 2-(Bromomethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolane-4-methanol; cis-[2-Bromomethyl-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl]methyl Benzoate

Database IDs

• CAS Number: 61397-56-6
• PubChem SID: 162257106
• PubChem CID: 1390983

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 6.1137466
• LogD (pH = 7.4): 6.1137466
• Log P: 6.1137466
• Molar Refractivity: 99.2657 cm^3
• Polarizability: 38.955425 Å^3
• Polar Surface Area: 44.76 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 118-120°C

Safety Information

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

DETAILS

Toronto Research Chemicals - B685405

cis-[2-Bromomethyl-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl]methyl Benzoate is an intermediate in the preparation of antifungal agents such as Ketoconazole (K186000), Itraconazole (I937500) and Terconazole.

REFERENCES

• Heeres, J. et al.: J. Med. Chem., 26, 611 (1983)