(1S,10R,11S,15S)-5-(benzyloxy)-15-methyltetracyclo[8.7.0.02,7.011,15]heptadeca-2,4,6,12-tetraen-14-one

• ChemBase ID: 161476
• Molecular Formular: C25H26O2
• Molecular Mass: 358.47274
• Monoisotopic Mass: 358.19328007
• SMILES: c1c(cc2c(c1)[C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)(C(=O)C=C2)C)OCc1ccccc1
• Canonical SMILES: O=C1C=C[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCc2c1ccc(c2)OCc1ccccc1
• InChI: InChI=1S/C25H26O2/c1-25-14-13-21-20-10-8-19(27-16-17-5-3-2-4-6-17)15-18(20)7-9-22(21)23(25)11-12-24(25)26/h2-6,8,10-12,15,21-23H,7,9,13-14,16H2,1H3/t21-,22-,23+,25+/m1/s1
• InChIKey: UJOCQXHOSBJACO-AHCIIZGASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,10R,11S,15S)-5-(benzyloxy)-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6,12-tetraen-14-one
• IUPAC Traditional name: (1S,10R,11S,15S)-5-(benzyloxy)-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6,12-tetraen-14-one
• Synonyms: 3-(Phenylmethoxy)-estra-1,3,5(10),15-tetraen-17-one; 3-(Benzyloxy)-estra-1,3,5(10),15-tetraen-17-one; 3-O-Benzyl 15,16-Dehydro Estrone

Database IDs

• CAS Number: 138743-03-0
• PubChem SID: 162255611
• PubChem CID: 15097971

CALCULATED PROPERTIES

• Acid pKa: 18.176182
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 6.17722
• LogD (pH = 7.4): 6.17722
• Log P: 6.17722
• Molar Refractivity: 109.2706 cm^3
• Polarizability: 42.05569 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Yellow Solid

DETAILS

Toronto Research Chemicals - B234560

Intermediate in the preparation of Estratrienes.

REFERENCES

• Labaree, D., et al.: J. Med. Chem., 46, 1886 (2003)
• Messinger, J., et al.: Mol. Cell. Endocrinol., 301, 216 (2003)