Substance
ID:715873
Names and Identifiers
IUPAC Traditional name
1,3-diethyl 2-oxopropanedioate
IUPAC name
1,3-diethyl 2-oxopropanedioate
Synonyms
Diethyl mesoxalateDiethyl ketomalonate酮基丙二酸二乙酯Diethyl oxomalonate
Registration numbers
MDL Number
CAS Number
Beilstein Number
EC Number
Merck Index
Properties
Physical Property
Melting Point
ca -70°C
Refractive Index
1.4175
Boiling Point
208-210°C
Density
0.927
Flash Point
>110°C(230°F)
Safety Information
Storage Warning
Moisture Sensitive
TSCA Listed
是
Product Information
Purity
95%
Molecule Details
No Data Available
Click here to submit data
Molecular Spectra
No Data Available
Click here to submit data
References
• Undergoes the Baylis-Hillman reaction in which a carbanionic species, generated by the reversible addition of 1,4-Diazabicyclo[2.2.2]octane, A14003, to a Michael acceptor, adds to the carbonyl group: Synth. Commun., 19, 2461 (1989).
• Thus, the reagent could be regarded as a CO2 equivalent in both the above sequences.
• Reacts with activated arenes under Friedel-Crafts conditions, or with aryllithium or Grignard derivatives, to give aryl hydroxymalonates, hydrolysis and decarboxylation of which gives substituted mandelic acids: Org. Synth. Coll., 3, 326 (1955). Alternatively, they may be transformed reductively to arylmalonates and hence to ester enolates: J. Org. Chem., 47, 4692 (1982).
• The carbonyl group behaves as a heterodienophile towards simple dienes. Curtius degradation of the gem-diester to carbonyl completes a synthesis of ?-unsaturated δ-lactones: Rocz. Chem., 38, 707 (1964); J. Am. Chem. Soc., 97, 6892 (1975); J. Org. Chem., 42, 4095 (1977):
• Ene-addition to alkenes occurs at the less-substituted carbon. Oxidative degradation leads to ?-unsaturated carboxylic acids: J. Am. Chem. Soc., 102, 2473 (1980); 106, 3797 (1984):
• For asymmetric Diels-Alder reaction, see: J. Chem. Soc., Chem. Commun., 676 (1987). For addition to aza-dienes, see: Tetrahedron Lett, 30, 2685 (1989).