(1R,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-17-hydroxy-2,13,15-trimethyl-5-oxo-14-(propanoyloxy)tetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-diene-14-carbothioic S-acid

• ChemBase ID: 167411
• Molecular Formular: C24H30F2O5S
• Molecular Mass: 468.5538064
• Monoisotopic Mass: 468.1782015
• SMILES: C1=CC(=O)C=C2[C@]1([C@@]1([C@@H](C[C@@H]2F)[C@H]2[C@](C[C@@H]1O)([C@]([C@@H](C2)C)(C(=O)S)OC(=O)CC)C)F)C
• Canonical SMILES: CCC(=O)O[C@]1(C(=O)S)[C@H](C)C[C@@H]2[C@]1(C)C[C@H](O)[C@]1([C@H]2C[C@@H](C2=CC(=O)C=C[C@]12C)F)F
• InChI: InChI=1S/C24H30F2O5S/c1-5-19(29)31-24(20(30)32)12(2)8-14-15-10-17(25)16-9-13(27)6-7-21(16,3)23(15,26)18(28)11-22(14,24)4/h6-7,9,12,14-15,17-18,28H,5,8,10-11H2,1-4H3,(H,30,32)/t12-,14+,15+,17+,18+,21+,22+,23+,24+/m1/s1
• InChIKey: QGESYFOFLPJDJW-CQRCZTONSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-17-hydroxy-2,13,15-trimethyl-5-oxo-14-(propanoyloxy)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-diene-14-carbothioic S-acid
• IUPAC Traditional name: (1R,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-17-hydroxy-2,13,15-trimethyl-5-oxo-14-(propanoyloxy)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-diene-14-carbothioic S-acid
• Synonyms: (6α,11β,16α,17α)-6,9-Difluoro-11-hydroxy-16-methyl-3-oxo-17-(1-oxopropoxy)-androsta-1,4-diene-17-carbothioic Acid; 6α,9α-Difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-(propionyloxy)-androsta-1,4-diene-17β-carbothioic Acid

Database IDs

• CAS Number: 80474-45-9
• PubChem SID: 162261544
• PubChem CID: 10053741

CALCULATED PROPERTIES

• Acid pKa: 0.38534895
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.3417096
• LogD (pH = 7.4): 2.3416667
• Log P: 3.4846485
• Molar Refractivity: 117.2552 cm^3
• Polarizability: 45.68399 Å^3
• Polar Surface Area: 80.67 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; DMF; Ethanol; Ethyl Acetate; Methanol
• Apperance: White Solid
• Melting Point: 158-160°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D445765

An intermediate in the synthesis of Fluticasone Propionate.

REFERENCES

• Meltzer, E.O., et al.: J. Allergy Clin. Immunol., 86, 221 (1990)
• Mitchison, H.C., et al.: Gut, 32, 260 (1990)
• Phillipps, G.H., et al.: J. Med. Chem., 37, 3717 (1994)