1-[4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-1,2,3,4-tetrahydropyrazin-1-yl]ethan-1-one

• ChemBase ID: 165651
• Molecular Formular: C26H26Cl2N4O4
• Molecular Mass: 529.41504
• Monoisotopic Mass: 528.13311069
• SMILES: C1=CN(CCN1C(=O)C)c1ccc(cc1)OC[C@H]1CO[C@@](O1)(c1ccc(cc1Cl)Cl)Cn1cncc1
• Canonical SMILES: Clc1ccc(c(c1)Cl)[C@]1(OC[C@@H](O1)COc1ccc(cc1)N1CCN(C=C1)C(=O)C)Cn1cncc1
• InChI: InChI=1S/C26H26Cl2N4O4/c1-19(33)31-10-12-32(13-11-31)21-3-5-22(6-4-21)34-15-23-16-35-26(36-23,17-30-9-8-29-18-30)24-7-2-20(27)14-25(24)28/h2-10,12,14,18,23H,11,13,15-17H2,1H3/t23-,26-/m0/s1
• InChIKey: GHVFISLXKPKRQU-OZXSUGGESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-1,2,3,4-tetrahydropyrazin-1-yl]ethan-1-one
• IUPAC Traditional name: 1-[4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-2,3-dihydropyrazin-1-yl]ethanone
• Synonyms: rel-1-[4-[4-[[(2R,4S)-2-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-3,4-dihydro-1(2H)-pyrazinyl]ethanone; rel-1-Acetyl-4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1,2,3,4-tetrahydropyrazine; R 049223; 2,3-Dehydro Ketoconazole

Database IDs

• CAS Number: 254912-63-5
• PubChem SID: 162259784
• PubChem CID: 71315319

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 3.73799
• LogD (pH = 7.4): 4.2027392
• Log P: 4.2656627
• Molar Refractivity: 137.4448 cm^3
• Polarizability: 53.014847 Å^3
• Polar Surface Area: 69.06 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D229700

Ketoconazole (K186000) impurity.

REFERENCES

• Heel, R., et al.: Drugs, 23, 1 (1982)
• Ballard, S., et al.: Biochem. Pharmacol., 37, 4643 (1982)