Tropone

• Catalog No.: L00473
• CAS Number: 539-80-0
• M. F.: C7H6O
• M. W.: 106.12194
• Purity: 97%

SYNONYMS

• Title: 环庚三烯酮
• IUPAC name: cyclohepta-2,4,6-trien-1-one
• IUPAC Traditional name: tropone
• Synonyms: Cycloheptatrienone

DATABASE IDS

• MDL Number: MFCD00014331
• CAS Number: 539-80-0
• EC Number: 208-725-6
• Beilstein Number: 1902335

PROPERTIES

• Purity: 97%
• Boiling Point: 91-92°C/4mm
• Density: 1.094
• Flash Point: >110°C(230°F)
• Refractive Index: 1.6150
• TSCA Listed: 否

REFERENCES

• Reacts as a diene in the Diels-Alder reaction with electron-rich alkenes (inverse electron-demand); see, e.g.: Org. Synth. Coll., 9, 396 (1998):
  
• Alternatively, reaction can occur with electron-deficient alkenes, as exemplified by phenyl vinyl sulfoxide. In this case, cyclic elimination leads directly to bicyclo[3.2.2]nona-3,6,8-trien-2-one in low yield: J. Org. Chem., 48, 3591 (1983). For a review of cycloadducts of tropone and its analogs with sulfenes and ketenes, see: Heterocycles, 18, 343 (1982).
• For cycloaddition reactions with kinetically stabilized phosphaalkynes, leading to tetracyclic phosphorus-carbon cage compounds, see: J. Org. Chem., 60, 5884 (1995); Synthesis, 87 (1996).
• Reacts with Grignard reagents at the 2-position (1,6-addition) as in the first step of a synthesis of the hydroazulene skeleton: Tetrahedron Lett., 23, 1863 (1982). Addition of various Li enolates again leads to 2-substituted 2,6-dihydrotropones in good yield: J. Org. Chem., 53, 4596 (1988).