4,10-dioxatricyclo[5.2.1.0^{2,6}]dec-8-ene-3,5-dione

• ChemBase ID: 83974
• Molecular Formular: C8H6O4
• Molecular Mass: 166.13084
• Monoisotopic Mass: 166.02660867
• SMILES: O1C(=O)C2C(C1=O)C1OC2C=C1
• Canonical SMILES: O=C1OC(=O)C2C1C1C=CC2O1
• InChI: InChI=1S/C8H6O4/c9-7-5-3-1-2-4(11-3)6(5)8(10)12-7/h1-6H
• InChIKey: QQYNRBAAQFZCLF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4,10-dioxatricyclo[5.2.1.0^{2,6}]dec-8-ene-3,5-dione; 4,10-dioxatricyclo[5.2.1.0^2,^6]dec-8-ene-3,5-dione
• IUPAC Traditional name: 4,10-dioxatricyclo[5.2.1.0^{2,6}]dec-8-ene-3,5-dione; 4,10-dioxatricyclo[5.2.1.0^2,^6]dec-8-ene-3,5-dione
• Synonyms: 4,10-dioxatricyclo[5.2.1.0~2,6~]dec-8-ene-3,5-dione; exo-3,6-Epoxy-1,2,3,6-tetrahydrophthalic anhydride; exo-7-Oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride; exo-7-氧杂二环[2.2.1]庚基-5-烯-2,3-二羧酸酐

Database IDs

• CAS Number: 5426-09-5; 6118-51-0
• EC Number: 226-570-2
• MDL Number: MFCD00151506; MFCD00077442
• Beilstein Number: 10355
• PubChem SID: 162071090
• PubChem CID: 98484

CALCULATED PROPERTIES

• Acid pKa: 18.15247
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.13038106
• LogD (pH = 7.4): 0.13038106
• Log P: -0.10295227
• Molar Refractivity: 37.2099 cm^3
• Polarizability: 14.710263 Å^3
• Polar Surface Area: 52.6 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 118-119°C

Safety Information

• Storage Warning: Moisture Sensitive
• RTECS: KC9650000
• European Hazard Symbols: Irritant (Xi)
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A

Product Information

• Purity: 98+%

REFERENCES

• Intermediate in a useful synthesis of 4,4-dialkyl-2-butenolides, based on reaction with two moles of Grignard reagent, followed by cycloreversion (elimination of furan) to release the double bond: J. Org. Chem., 47, 3953 (1982); Tetrahedron Lett., 24,1929 (1983):
  
• For a review of cycloreversion reactions in organic synthesis, see: Synthesis, 121 (1985).