(5R)-6,8-dioxabicyclo[3.2.1]oct-2-en-4-one

• ChemBase ID: 172282
• Molecular Formular: C6H6O3
• Molecular Mass: 126.11004
• Monoisotopic Mass: 126.03169405
• SMILES: C1=CC(=O)[C@@H]2OC1CO2
• Canonical SMILES: O=C1C=CC2O[C@@H]1OC2
• InChI: InChI=1S/C6H6O3/c7-5-2-1-4-3-8-6(5)9-4/h1-2,4,6H,3H2/t4?,6-/m1/s1
• InChIKey: HITOXZPZGPXYHY-BAFYGKSASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5R)-6,8-dioxabicyclo[3.2.1]oct-2-en-4-one
• IUPAC Traditional name: (5R)-6,8-dioxabicyclo[3.2.1]oct-2-en-4-one
• Synonyms: (1S,5R)-6,8-Dioxabicyclo[3.2.1]oct-2-en-4-one; 1,6-Anhydro-3,4-dideoxy-β-D-glycero-hex-3-enopyranose-2-ulose; Levoglucosenone

Database IDs

• CAS Number: 37112-31-5
• PubChem SID: 164228192
• PubChem CID: 12898918

CALCULATED PROPERTIES

• Acid pKa: 17.642475
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.55552113
• LogD (pH = 7.4): 0.55552113
• Log P: 0.55552113
• Molar Refractivity: 30.1336 cm^3
• Polarizability: 11.618892 Å^3
• Polar Surface Area: 35.53 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Colourless to Yellow Oil

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - L375000

(-)-Form is a pyrolysis product of cellulose and cellulose-containing materials including pulp and paper waste products.Known as a pyrolytic product of cellulose, its very useful as a chiral source for synthesizing natural products because of its highly f

REFERENCES

• Essig, M.G., et al.: Carbohydr. Res., 156, 225 (1986)
• Taniguchi, T., et al.: Synlett, 971 (1986)