(1S,2R,10R,11S,14R,15S)-15-ethyl-14-ethynyl-14-[(trimethylsilyl)oxy]tetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one

• ChemBase ID: 175659
• Molecular Formular: C24H36O2Si
• Molecular Mass: 384.62694
• Monoisotopic Mass: 384.24845692
• SMILES: C1C(=O)C=C2[C@H](C1)[C@@H]1[C@@H](CC2)[C@H]2[C@@](CC1)(CC)[C@@](CC2)(C#C)O[Si](C)(C)C
• Canonical SMILES: CC[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O[Si](C)(C)C)CCC1=CC(=O)CC[C@H]31
• InChI: InChI=1S/C24H36O2Si/c1-6-23-14-12-20-19-11-9-18(25)16-17(19)8-10-21(20)22(23)13-15-24(23,7-2)26-27(3,4)5/h2,16,19-22H,6,8-15H2,1,3-5H3/t19-,20+,21+,22-,23-,24-/m0/s1
• InChIKey: ZXHQGVWYEGMCCY-ZUYVPRDGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,14R,15S)-15-ethyl-14-ethynyl-14-[(trimethylsilyl)oxy]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• IUPAC Traditional name: (1S,2R,10R,11S,14R,15S)-15-ethyl-14-ethynyl-14-[(trimethylsilyl)oxy]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• Synonyms: (17α)-13-Ethyl-17-[(trimethylsilyl)oxy]-18,19-dinorpregn-4-en-20-yn-3-one; 17α-Ethynyl-18-methyl-17-(trimethylsiloxy)-19-norandrost-4-en-3-one; D-(-)-Norgestrel Trimethylsilyl Ether

Database IDs

• CAS Number: 39942-01-3
• PubChem SID: 164231569
• PubChem CID: 13368656

CALCULATED PROPERTIES

• Acid pKa: 19.278177
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 5.6435
• LogD (pH = 7.4): 5.6435
• Log P: 5.6435
• Molar Refractivity: 108.1514 cm^3
• Polarizability: 44.379345 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Acetone; Dichloromethane; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - N689545

Protected D-(-)-Norgestrel (N689510), an emergency contraceptive.

REFERENCES

• Fotherby, K., et al.: J. Steroid Biochem., 19(1C), 817 (1983)
• Stanczyk, F. Z., et al.: Contraception, 42, 67 (1983)
• Bednarek, P., et al.: Drugs, 67, 2478 (1983)