NAMES AND DATABASE IDS
NAMES AND DATABASE IDS
Names Database IDs
IUPAC name
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1,3-diethyl 2-oxopropanedioate
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IUPAC Traditional name
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1,3-diethyl 2-oxopropanedioate
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Synonyms
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Diethyl 2-oxopropane-1,3-dioate
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Diethyl ketomalonate
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Diethyl 2-oxomalonate 97%
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Diethyl ketomalonate
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Diethyl mesoxalate
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Ketomalonic acid diethyl ester
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Diethyl ketomalonate
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Diethyl mesoxalate
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Diethyl oxomalonate
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Diethyl mesoxalate
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2-氧代丙二酸二乙酯
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二乙基双乙烯酯
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酮基丙二酸二乙酯
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酮基丙二酸二乙酯
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丙酮二酸二乙酯
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CAS Number
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EC Number
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MDL Number
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Beilstein Number
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Merck Index
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PubChem SID
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PubChem CID
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DATA SOURCES
DATA SOURCES
All Sources Commercial Sources Non-commercial Sources
CALCULATED PROPERTIES
CALCULATED PROPERTIES
JChem
H Acceptors
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3
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H Donor
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0
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LogD (pH = 5.5)
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1.4975388
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LogD (pH = 7.4)
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1.4975388
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Log P
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1.4975388
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Molar Refractivity
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38.82 cm3
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Polarizability
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15.412765 Å3
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Polar Surface Area
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69.67 Å2
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Rotatable Bonds
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6
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Lipinski's Rule of Five
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true
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DETAILS
DETAILS
MP Biomedicals
Sigma Aldrich
Sigma Aldrich -
D97401
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Packaging 5, 25 g in glass bottle Application Reagent employed in Wittig and Aza-Wittig reactions for synthesis of triazoles1 and 2-azadienes,2 respectively. |
Sigma Aldrich -
63970
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Other Notes Reactions with olefins to allylcarboxylic acids1; DA cycloaddition to heterocycles2,3 |
REFERENCES
REFERENCES
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- • 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).
- • Thus, the reagent could be regarded as a CO2 equivalent in both the above sequences.
- • 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).
- • 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).
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PATENTS
PATENTS
PubChem Patent
Google Patent