(10'S,11'S,15'S)-15'-methylspiro[1,3-dioxolane-2,5'-tetracyclo[8.7.0.02,7.011,15]heptadecane]-1'(17'),2'(7')-dien-14'-one

• ChemBase ID: 168196
• Molecular Formular: C20H26O3
• Molecular Mass: 314.41864
• Monoisotopic Mass: 314.18819469
• SMILES: C1CC2(CC3=C1C1=CC[C@]4([C@H]([C@@H]1CC3)CCC4=O)C)OCCO2
• Canonical SMILES: O=C1CC[C@@H]2[C@]1(C)CC=C1[C@H]2CCC2=C1CCC1(C2)OCCO1
• InChI: InChI=1S/C20H26O3/c1-19-8-6-15-14-7-9-20(22-10-11-23-20)12-13(14)2-3-16(15)17(19)4-5-18(19)21/h6,16-17H,2-5,7-12H2,1H3/t16-,17+,19+/m1/s1
• InChIKey: XUOQKQRMICQUQC-AOIWGVFYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (10'S,11'S,15'S)-15'-methylspiro[1,3-dioxolane-2,5'-tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecane]-1'(17'),2'(7')-dien-14'-one
• IUPAC Traditional name: (10'S,11'S,15'S)-15'-methylspiro[1,3-dioxolane-2,5'-tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecane]-1'(17'),2'(7')-dien-14'-one
• Synonyms: 3,3-(Ethylenedioxy)estra-5(10),9(11)-dien-17-one; Cyclic 3-(1,2-Ethanediyl Acetal)-estra-5(10),9(11)-diene-3,17-dione; Estra-5(10),9(11)-diene-3,17-dione 3-Ethylene Ketal; Estradiene dione-3-keta

Database IDs

• CAS Number: 5571-36-8
• MDL Number: MFCD08062585
• PubChem SID: 162262328
• PubChem CID: 7076399

CALCULATED PROPERTIES

• Acid pKa: 19.859175
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.0800617
• LogD (pH = 7.4): 3.0800617
• Log P: 3.0800617
• Molar Refractivity: 89.9887 cm^3
• Polarizability: 34.894592 Å^3
• Polar Surface Area: 35.53 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 152-154°C

Safety Information

• Storage Condition: -20°C Freezer

Product Information

• Purity: 95+%

DETAILS

Toronto Research Chemicals - E668600

Mifepristone intermediate; antiprogestational antiglucocorticoid antagonist steroidal spirooxazole.

REFERENCES

• Agarwai, M., et al.: Pharmacol. Ther., 70, 183 (1996)
• Fuhrmann, U., et al.: J. Med. Chem., 43, 5010 (1996)
• Spitz, I., et al.: Steroids, 65, 807 (1996)
• Tang, O., et al.: Gynecol. Endocrinol., 22, 655 (1996)
• Kang, F., et al.: Bioorg. Med. Chem. Lett.,