(1R,2S,4S,6S)-9-(4-methoxyphenyl)-3,8,10-trioxatricyclo[4.4.0.02,4]decane

• ChemBase ID: 169713
• Molecular Formular: C14H16O4
• Molecular Mass: 248.27444
• Monoisotopic Mass: 248.10485899
• SMILES: [C@H]12[C@H](C[C@@H]3[C@H]1OC(OC3)c1ccc(cc1)OC)O2
• Canonical SMILES: COc1ccc(cc1)C1OC[C@H]2[C@@H](O1)[C@H]1O[C@H]1C2
• InChI: InChI=1S/C14H16O4/c1-15-10-4-2-8(3-5-10)14-16-7-9-6-11-13(17-11)12(9)18-14/h2-5,9,11-14H,6-7H2,1H3/t9-,11-,12+,13-,14?/m0/s1
• InChIKey: IBFVDAHLIIWJTI-UUJNGGQRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,4S,6S)-9-(4-methoxyphenyl)-3,8,10-trioxatricyclo[4.4.0.0^2,^4]decane
• IUPAC Traditional name: (1R,2S,4S,6S)-9-(4-methoxyphenyl)-3,8,10-trioxatricyclo[4.4.0.0^2,^4]decane
• Synonyms: (1aS,1bR,5aS,6aS)-Hexahydro-3-(4-methoxyphenyl)-oxireno[4,5]cyclopenta[1,2-d][1,3]dioxin

Database IDs

• CAS Number: 905580-85-0
• PubChem SID: 162263845
• PubChem CID: 58944649

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 1.8252801
• LogD (pH = 7.4): 1.8252801
• Log P: 1.8252801
• Molar Refractivity: 63.5357 cm^3
• Polarizability: 25.640457 Å^3
• Polar Surface Area: 36.92 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - H294140

Used in the preparation of nucleoside derivatives as antitumor agents, E1 activating enzymes and MLN4924, an inhibitor of NEDD8-activating enzyme.

REFERENCES

• Soucy, T. et al.; Nature 458, 732 (2009)