(3aR,4S,5R,6aS)-4-(hydroxymethyl)-2-oxo-hexahydro-2H-cyclopenta[b]furan-5-yl benzoate

• ChemBase ID: 164964
• Molecular Formular: C15H16O5
• Molecular Mass: 276.28454
• Monoisotopic Mass: 276.09977361
• SMILES: [C@H]12[C@H](C[C@H]([C@@H]1CO)OC(=O)c1ccccc1)OC(=O)C2
• Canonical SMILES: OC[C@H]1[C@@H](C[C@H]2[C@@H]1CC(=O)O2)OC(=O)c1ccccc1
• InChI: InChI=1S/C15H16O5/c16-8-11-10-6-14(17)19-12(10)7-13(11)20-15(18)9-4-2-1-3-5-9/h1-5,10-13,16H,6-8H2/t10-,11-,12+,13-/m1/s1
• InChIKey: OBRRYUZUDKVCOO-FVCCEPFGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3aR,4S,5R,6aS)-4-(hydroxymethyl)-2-oxo-hexahydro-2H-cyclopenta[b]furan-5-yl benzoate
• IUPAC Traditional name: (3aR,4S,5R,6aS)-4-(hydroxymethyl)-2-oxo-hexahydrocyclopenta[b]furan-5-yl benzoate
• Synonyms: (3aR,4S,5R,6aS)-5-(Benzoyloxy)hexahydro-4-(hydroxymethyl)-2H-cyclopenta[b]furan-2-one; [3aR-(3aα,4α,5β,6aα)]-5-(Benzoyloxy)hexahydro-4-(hydroxymethyl)-2H-cyclopenta[b]furan-2-one; PGX 4; (-)-Corey Lactone Benzoate

Database IDs

• CAS Number: 39746-00-4
• PubChem SID: 162259098
• PubChem CID: 2724454

CALCULATED PROPERTIES

• Acid pKa: 15.374329
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.9955339
• LogD (pH = 7.4): 0.9955339
• Log P: 0.9955339
• Molar Refractivity: 69.6697 cm^3
• Polarizability: 27.620045 Å^3
• Polar Surface Area: 72.83 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C694990

(-)-Corey Lactone Benzoate is a corey lactone derivative used in the preparation prostaglandin analogues for use as vasolidator as well as EP4 receptor agonists.

REFERENCES

• Ohta, C. et al.: J. Org. Chem., 74, 8298 (2009)
• Skuballa, W. et al.: Angew. Chem., 93, 1080 (2009)
• Andersen, N.H. et al.: Prostaglandins, 22, 809 (2009)