methyl 2-hydroxy-2-[5-oxo-2-(propan-2-yloxy)oxan-4-yl]propanoate

• ChemBase ID: 178354
• Molecular Formular: C12H20O6
• Molecular Mass: 260.2836
• Monoisotopic Mass: 260.12598836
• SMILES: C1OC(CC(C1=O)C(C(=O)OC)(O)C)OC(C)C
• Canonical SMILES: COC(=O)C(C1CC(OCC1=O)OC(C)C)(O)C
• InChI: InChI=1S/C12H20O6/c1-7(2)18-10-5-8(9(13)6-17-10)12(3,15)11(14)16-4/h7-8,10,15H,5-6H2,1-4H3
• InChIKey: XEXIPMYISVSJSK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 2-hydroxy-2-[5-oxo-2-(propan-2-yloxy)oxan-4-yl]propanoate
• IUPAC Traditional name: methyl 2-hydroxy-2-(2-isopropoxy-5-oxooxan-4-yl)propanoate
• Synonyms: Tetrahydro-α-hydroxy-α-methyl-2-(1-methylethoxy)-5-oxo-2H-pyran-4-acetic acid Methyl Ester

Database IDs

• CAS Number: 1044244-99-6
• PubChem SID: 164234264
• PubChem CID: 24970949

CALCULATED PROPERTIES

• Acid pKa: 10.94292
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 0.5135584
• LogD (pH = 7.4): 0.5134365
• Log P: 0.51355994
• Molar Refractivity: 62.2639 cm^3
• Polarizability: 25.080524 Å^3
• Polar Surface Area: 82.06 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate
• Apperance: Colorless Oil

DETAILS

Toronto Research Chemicals - T293660

Used in the preparation of germination stimulant furopyranones.

REFERENCES

• Nagase, R. et al.; Tetrahedron Lett. 49, 4509 (2008)