(1'R,5'S,6'S,9'S,10'S,13'R)-5'-methyl-6'-(prop-1-yn-1-yl)-18'-oxaspiro[1,3-dioxolane-2,15'-pentacyclo[11.4.1.01,13.02,10.05,9]octadecan]-2'-en-6'-ol

• ChemBase ID: 168116
• Molecular Formular: C23H30O4
• Molecular Mass: 370.4819
• Monoisotopic Mass: 370.21440944
• SMILES: C1CC2(C[C@@]34[C@@]1(C1=CC[C@]5([C@H]([C@@H]1CC3)CC[C@@]5(O)C#CC)C)O4)OCCO2
• Canonical SMILES: CC#C[C@]1(O)CC[C@@H]2[C@]1(C)CC=C1[C@H]2CC[C@@]23[C@]1(CCC1(C3)OCCO1)O2
• InChI: InChI=1S/C23H30O4/c1-3-7-20(24)9-6-17-16-4-10-21-15-22(25-13-14-26-22)11-12-23(21,27-21)18(16)5-8-19(17,20)2/h5,16-17,24H,4,6,8-15H2,1-2H3/t16-,17-,19-,20-,21+,23+/m0/s1
• InChIKey: NRUIWWWJNIPUBD-XZJZWBLTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1'R,5'S,6'S,9'S,10'S,13'R)-5'-methyl-6'-(prop-1-yn-1-yl)-18'-oxaspiro[1,3-dioxolane-2,15'-pentacyclo[11.4.1.0^1,^1^3.0^2,^1^0.0^5,^9]octadecan]-2'-en-6'-ol
• IUPAC Traditional name: (1'R,5'S,6'S,9'S,10'S,13'R)-5'-methyl-6'-(prop-1-yn-1-yl)-18'-oxaspiro[1,3-dioxolane-2,15'-pentacyclo[11.4.1.0^1,^1^3.0^2,^1^0.0^5,^9]octadecan]-2'-en-6'-ol
• Synonyms: 5α,10α-Epoxy-3,3-(ethylenedioxy)-17β-hydroxy-17α-(1-propynyl)-9(11)-estrene; 5α,10α-Epoxy-17β-hydroxy-17-(1-propynyl)estr-9(11)-en-3-one Cyclic Ethylene Acetal; (5α,10α,17β)-5,10-Epoxy-17-hydroxy-17-(1-propyn-1-yl)-estr-9(11)-en-3-one Cyclic 1,2-Ethanediyl Acetal

Database IDs

• CAS Number: 84371-57-3
• PubChem SID: 162262248
• PubChem CID: 10547150

CALCULATED PROPERTIES

• Acid pKa: 17.926292
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.3193154
• LogD (pH = 7.4): 3.3193154
• Log P: 3.3193154
• Molar Refractivity: 102.0227 cm^3
• Polarizability: 40.083477 Å^3
• Polar Surface Area: 51.22 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 122-125°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - E589210

Intermediate in the preparation of Mifepristone derivatives.

REFERENCES

• Jiang, W., et al.: Bioorg. Med. Chem. Lett., 17, 1471 (2007)