2,7-dichloro-4-[2-(dibutylamino)-1-hydroxyethyl]-9H-fluoren-9-one

• ChemBase ID: 166202
• Molecular Formular: C23H27Cl2NO2
• Molecular Mass: 420.37198
• Monoisotopic Mass: 419.14188447
• SMILES: c12c3c(C(=O)c1cc(cc2C(O)CN(CCCC)CCCC)Cl)cc(cc3)Cl
• Canonical SMILES: CCCCN(CC(c1cc(Cl)cc2c1c1ccc(cc1C2=O)Cl)O)CCCC
• InChI: InChI=1S/C23H27Cl2NO2/c1-3-5-9-26(10-6-4-2)14-21(27)19-12-16(25)13-20-22(19)17-8-7-15(24)11-18(17)23(20)28/h7-8,11-13,21,27H,3-6,9-10,14H2,1-2H3
• InChIKey: DHSOIDFQNPRZLM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,7-dichloro-4-[2-(dibutylamino)-1-hydroxyethyl]-9H-fluoren-9-one
• IUPAC Traditional name: 2,7-dichloro-4-[2-(dibutylamino)-1-hydroxyethyl]fluoren-9-one
• Synonyms: 2,7-Dichloro-4-[2-(dibutylamino)-1-hydroxyethyl]-9H-fluoren-9-one; Lumefantrine Keto Impurity; 9-Des[(4-chlorophenyl)methylene]-9-oxo Lumefantrine

Database IDs

• CAS Number: 53221-25-3
• PubChem SID: 162260335
• PubChem CID: 57350587

CALCULATED PROPERTIES

• Acid pKa: 14.049762
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.062174
• LogD (pH = 7.4): 4.6456313
• Log P: 6.2735276
• Molar Refractivity: 117.5737 cm^3
• Polarizability: 46.891895 Å^3
• Polar Surface Area: 40.54 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D289035

An impurity of Lumefantrine (L474000) with antimalarial activity.

REFERENCES

• Beutler, U. et al.: Org. Proc. Res. Dev., 11, 341 (2007)
• Atkinson, E. et al.: J. Med. Chem., 17, 1009 (2007)