(1S,2R,10R,11S,15R)-15-ethyltetracyclo[8.7.0.02,7.011,15]heptadec-6-ene-5,14-dione

• ChemBase ID: 168588
• Molecular Formular: C19H26O2
• Molecular Mass: 286.40854
• Monoisotopic Mass: 286.19328007
• SMILES: C1C(=O)C=C2[C@H](C1)[C@@H]1[C@@H](CC2)[C@H]2[C@@](CC1)(C(=O)CC2)CC
• Canonical SMILES: CC[C@]12CC[C@H]3[C@H]([C@@H]2CCC1=O)CCC1=CC(=O)CC[C@H]31
• InChI: InChI=1S/C19H26O2/c1-2-19-10-9-15-14-6-4-13(20)11-12(14)3-5-16(15)17(19)7-8-18(19)21/h11,14-17H,2-10H2,1H3/t14-,15+,16+,17-,19+/m0/s1
• InChIKey: SBLHOJQRZNGHLQ-WAXPSYRMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,15R)-15-ethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-ene-5,14-dione
• IUPAC Traditional name: (1S,2R,10R,11S,15R)-15-ethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-ene-5,14-dione
• Synonyms: 13-Ethyl-gon-4-ene-3,17-dione; (+)-13-Ethylgon-4-ene-3,17-dione; (+)-13-β-Ethylgon-4-ene-3,17-dione; 18-Methyl-19-norandrost-4-ene-3,17-dione; 18-Methylestr-4-ene-3,17-dione; D-Ethyl Gonendione

Database IDs

• CAS Number: 21800-83-9
• PubChem SID: 162262720
• PubChem CID: 71316596

CALCULATED PROPERTIES

• Acid pKa: 19.186764
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 4.0734725
• LogD (pH = 7.4): 4.0734725
• Log P: 4.0734725
• Molar Refractivity: 83.7334 cm^3
• Polarizability: 32.712193 Å^3
• Polar Surface Area: 34.14 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White Solid
• Melting Point: 166-167°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - E918600

Norgestrel intermediate.

REFERENCES

• Hiraga, K., et al.: Chem. Pharm. Bull., 13, 1289 (1965)
• Bergink, F.W., et al.: J. Steroid Biochem., 14, 175 (1965)
• Phillips, A., et al.: Contraception, 36, 181 (1965)
• Corson, S.L., et al.: Am. J. Obstet. Gynecol., 168, 1017 (1965)