(2S,6'R)-2',4,6-trimethoxy-6'-methyl-3H-spiro[1-benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dione

• ChemBase ID: 165526
• Molecular Formular: C17H18O6
• Molecular Mass: 318.32122
• Monoisotopic Mass: 318.1103383
• SMILES: c1c(cc2c(c1OC)C(=O)[C@]1(O2)[C@@H](CC(=O)C=C1OC)C)OC
• Canonical SMILES: COc1cc2O[C@@]3(C(=O)c2c(c1)OC)[C@H](C)CC(=O)C=C3OC
• InChI: InChI=1S/C17H18O6/c1-9-5-10(18)6-14(22-4)17(9)16(19)15-12(21-3)7-11(20-2)8-13(15)23-17/h6-9H,5H2,1-4H3/t9-,17+/m1/s1
• InChIKey: QPCYNIYZPDJCMB-XLFHBGCDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,6'R)-2',4,6-trimethoxy-6'-methyl-3H-spiro[1-benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dione
• IUPAC Traditional name: (2S,6'R)-2',4,6-trimethoxy-6'-methylspiro[1-benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dione
• Synonyms: (1'S,6'R)-2',4,6-Trimethoxy-6'-methylspiro[benzofuran-2(3H),1'-[2]cyclohexene]-3,4'-dione; (1'S-trans)-2',4,6-Trimethoxy-6'-methylspiro[benzofuran-2(3H),1'-[2]cyclohexene]-3,4'-dione; 7-Dechlorogriseofulvin; Dechlorogriseofulvin; 7-Dechloro Griseofulvin

Database IDs

• CAS Number: 3680-32-8
• PubChem SID: 162259659
• PubChem CID: 24066885

CALCULATED PROPERTIES

• Acid pKa: 17.687458
• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 1.5680928
• LogD (pH = 7.4): 1.5680928
• Log P: 1.5680928
• Molar Refractivity: 83.0411 cm^3
• Polarizability: 31.794481 Å^3
• Polar Surface Area: 71.06 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Ethyl Acetate
• Apperance: White Solid
• Melting Point: 177-179°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D226450

A major photoproduct (impurity) of Griseofulvin (G787500).

REFERENCES

• Mantle, P., et al.: J. Gen. Microbiol., 130, 1293 (1984)
• Boonphong, S., et al.: J. Nat. Prod., 64, 965 (1984)