(1R,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-17-hydroxy-14-{[(iodomethyl)sulfanyl]carbonyl}-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-14-yl (3,3,3-2H3)propanoate

• ChemBase ID: 171683
• Molecular Formular: C25H31F2IO5S
• Molecular Mass: 608.4769164
• Monoisotopic Mass: 608.09049953
• SMILES: C1=C[C@]2(C(=CC1=O)[C@H](C[C@@H]1[C@@]2([C@H](C[C@]2([C@H]1C[C@H]([C@@]2(C(=O)SCI)OC(=O)CC)C)C)O)F)F)C
• Canonical SMILES: ICSC(=O)[C@@]1(OC(=O)CC)[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/C25H31F2IO5S/c1-5-20(31)33-25(21(32)34-12-28)13(2)8-15-16-10-18(26)17-9-14(29)6-7-22(17,3)24(16,27)19(30)11-23(15,25)4/h6-7,9,13,15-16,18-19,30H,5,8,10-12H2,1-4H3/t13-,15+,16+,18+,19+,22+,23+,24+,25+/m1/s1
• InChIKey: HKRIRGIBBWVEFV-CENSZEJFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-17-hydroxy-14-{[(iodomethyl)sulfanyl]carbonyl}-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl (3,3,3-^2H₃)propanoate
• IUPAC Traditional name: (1R,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-17-hydroxy-14-{[(iodomethyl)sulfanyl]carbonyl}-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl (3,3,3-^2H₃)propanoate
• Synonyms: 5-Iodomethyl 6α,9α-Difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-(3,3,3-d3-propionyloxy)-androsta-1,4-diene-17β-carbothioate

Database IDs

• PubChem SID: 164227593
• PubChem CID: 45039582

CALCULATED PROPERTIES

• Acid pKa: 13.557201
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 4.7972775
• LogD (pH = 7.4): 4.7972775
• Log P: 4.7972775
• Molar Refractivity: 134.6256 cm^3
• Polarizability: 52.629223 Å^3
• Polar Surface Area: 80.67 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; DMF; Ethanol; Ethyl Acetate; Methanol
• Apperance: Off-White Solid
• Melting Point: 195-197°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - I709005

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)