(2R,4S,5R,6R,7R,9S,18R)-6-(2-chloroacetyl)-6-hydroxy-5,7,18-trimethyl-3-oxapentacyclo[8.8.0.02,4.05,9.013,18]octadeca-13,16-dien-15-one

• ChemBase ID: 170335
• Molecular Formular: C22H27ClO4
• Molecular Mass: 390.90038
• Monoisotopic Mass: 390.15978702
• SMILES: C1=C[C@]2(C(=CC1=O)CCC1C2[C@@H]2[C@H]([C@]3([C@H]1C[C@H]([C@@]3(C(=O)CCl)O)C)C)O2)C
• Canonical SMILES: ClCC(=O)[C@@]1(O)[C@H](C)C[C@@H]2[C@]1(C)[C@@H]1O[C@@H]1C1C2CCC2=CC(=O)C=C[C@]12C
• InChI: InChI=1S/C22H27ClO4/c1-11-8-15-14-5-4-12-9-13(24)6-7-20(12,2)17(14)18-19(27-18)21(15,3)22(11,26)16(25)10-23/h6-7,9,11,14-15,17-19,26H,4-5,8,10H2,1-3H3/t11-,14?,15+,17?,18-,19-,20+,21-,22+/m1/s1
• InChIKey: BFRHEEZSFDINDL-LGYQFSFISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4S,5R,6R,7R,9S,18R)-6-(2-chloroacetyl)-6-hydroxy-5,7,18-trimethyl-3-oxapentacyclo[8.8.0.0^2,^4.0^5,^9.0^1^3,^1^8]octadeca-13,16-dien-15-one
• IUPAC Traditional name: (2R,4S,5R,6R,7R,9S,18R)-6-(2-chloroacetyl)-6-hydroxy-5,7,18-trimethyl-3-oxapentacyclo[8.8.0.0^2,^4.0^5,^9.0^1^3,^1^8]octadeca-13,16-dien-15-one
• Synonyms: 17α-Hydroxy-21-chloro-9β,11β-epoxy-16α-methylpregna-1,4-diene-3,20-dione

Database IDs

• PubChem SID: 164226245
• PubChem CID: 71748928

CALCULATED PROPERTIES

• Acid pKa: 12.421569
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.235262
• LogD (pH = 7.4): 3.2352579
• Log P: 3.235262
• Molar Refractivity: 103.7133 cm^3
• Polarizability: 40.43426 Å^3
• Polar Surface Area: 66.9 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - H915450

An intermediate in the synthesis of deuterated Mometason Furoate, a topical corticosteroid intermediate of used as an anti-inflammatory.

REFERENCES

• Shapiro, E.L., et al.: J. Med. Chem., 30, 1581 (1987)
• Graft, D., et al.: J. Allergy Clin. Immunol., 98, 724 (1996)