Compounds > diethyl (ethoxymethylene)malonate
Page last updated: 2024-12-05

diethyl (ethoxymethylene)malonate

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Diethyl (ethoxymethylene)malonate, also known as Knoevenagel's reagent, is a versatile reagent in organic synthesis. It is a key component in the Knoevenagel condensation reaction, a widely used method for forming carbon-carbon bonds. This reaction involves the condensation of an aldehyde or ketone with an active methylene compound, such as diethyl (ethoxymethylene)malonate, in the presence of a base. The resulting product is an α,β-unsaturated carbonyl compound, which can be further functionalized in various ways. The reagent is also used in other reactions like Michael addition and Claisen condensation. The study of diethyl (ethoxymethylene)malonate is important due to its role in the synthesis of various organic compounds, including pharmaceuticals, natural products, and agrochemicals.'

Cross-References

ID SourceID
PubMed CID6871
SCHEMBL ID50838
MeSH IDM0129865

Synonyms (98)

Synonym
diethyl (ethoxymethylidene)propanedioate
2-(ethoxy-methylene)-propanedioic acid diethyl ester
propanedioic acid, (ethoxymethylene)-, diethyl ester
malonic acid, (ethoxymethylene)-, diethyl ester
ai3-04025
brn 0880058
einecs 201-725-7
diethyl emme
nsc 62117
diethyl ethoxymethylenemalonate
tl 1483
ethoxymethylenemalonic acid, ethyl ester
nsc-62117
nsc62117
nsc9068
ethoxymethylenemalonic acid diethyl ester
87-13-8
diethyl (ethoxymethylene)malonate
nsc-9068
diethyl 2-(ethoxymethylene)propanedioate
(ethoxy-methylene)malonic acid, diethyl ester
inchi=1/c10h16o5/c1-4-13-7-8(9(11)14-5-2)10(12)15-6-3/h7h,4-6h2,1-3h
diethyl ethoxymethylenemalonate, 99%
NCIOPEN2_003690
diethyl 2-(ethoxymethylidene)propanedioate
E0255
diethyl(ethoxymethylene)malonate
AKOS000120084
1,3-diethyl 2-(ethoxymethylidene)propanedioate
ethyl ethoxymethylene malonate
(ethoxymethylene)propanedioic acid diethyl ester
2-(1-sec-butoxypropylidene)malonic acid;diethyl ethoxymethylenemalonate
6kf8220sz8 ,
propanedioic acid, 2-(ethoxymethylene)-, 1,3-diethyl ester
4-03-00-01192 (beilstein handbook reference)
ec 201-725-7
unii-6kf8220sz8
ethyl 3-ethoxy-2-(ethoxymethylene)-3-oxopropanoate
diethyl 2-(ethoxymethylene)malonate
diethyl ethoxymethylidenemalonate
(ethoxymethylene)malonic acid diethyl ester
FT-0624839
SCHEMBL50838
BBL027740
2-ethoxy-1,1-bis-(ethoxycarbonyl)ethene
diethyl [(ethyloxy)methylidene]propanedioate
2-ethoxy-1,1-bis(ethoxycarbonyl)ethene
diethyl-ethoxymethylene-malonate
diethyl-2-(ethoxymethylene)malonate
ethoxymethylenemalonic diethylester
diethyl ethoxy-methylene-malonate
diethyl (ethoxymethylidene)-malonate
2-ethoxymethylene malonic acid diethyl ester
ethoxymethylene-malonic acid diethyl ester
diethyl ethoxymethylene malonate
diethyl ethoxymethylene-malonate
diethyl ethoxymethylenepropanediate
ethoxymethylene malonic acid diethyl ester
2-ethoxymethylenemalonic acid diethyl ester
diethyl(ethoxymethylidene)propanedioate
1,1-bis(ethoxycarbonyl)-2-ethoxyethylene
diethyl ethoxymethylenepropanedioate
diethyl 2-(ethoxymethylene)-malonate
diethyl ethoxymethylenepropandioate
diethyl ethoxymethylenmalonate
2-ethoxymethylene-malonic acid diethyl ester
diethyl 2-ethoxymethylenemalonate
2-(ethoxymethylene)-malonic acid diethyl ester
(ethoxymethylene)propanedioic acid, diethyl ester
ethoxymethylene malonic acid-diethyl ester
dtxsid5052591 ,
tox21_303975
cas-87-13-8
NCGC00357199-01
dtxcid2031164
diethyl 2-(ethoxymethylene)malonate #
diethyl((ethyloxy)methylidene)propanedioate
2-(ethoxymethylene)malonic acid diethyl ester
diethyl 2-ethoxymethylidene malonate
F0001-2159
mfcd00009148
sr-01000944699
SR-01000944699-1
diethyl ethoxymethylenemalonate, for lc-ms derivatization, >=98.0% (gc)
nalidixic acid impurity c, europepharmacopoeia (ep) reference standard
SY001564
DS-6667
BCP04784
CS-0019402
EN300-19129
STL185546
AMY402
AC7837
Q27265050
deemm
PB43640
diethyl2-(ethoxymethylene)malonate
nalidixic acid impurity c
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (13)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (7.69)18.7374
1990's2 (15.38)18.2507
2000's1 (7.69)29.6817
2010's8 (61.54)24.3611
2020's1 (7.69)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 38.25

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index38.25 (24.57)
Research Supply Index2.64 (2.92)
Research Growth Index5.17 (4.65)
Search Engine Demand Index48.84 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (38.25)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other13 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
carbamates
[no description available]		2.2510amino-acid anion
histamine
[no description available]		2.0710aralkylamino compound;
imidazoles		human metabolite;
mouse metabolite;
neurotransmitter
mercaptoethanol
Mercaptoethanol: A water-soluble thiol derived from hydrogen sulfide and ethanol. It is used as a reducing agent for disulfide bonds and to protect sulfhydryl groups from oxidation.		2.0610alkanethiol;
primary alcohol		geroprotector
dimercaprol
Dimercaprol: An anti-gas warfare agent that is effective against Lewisite (dichloro(2-chlorovinyl)arsine) and formerly known as British Anti-Lewisite or BAL. It acts as a chelating agent and is used in the treatment of arsenic, gold, and other heavy metal poisoning.. dimercaprol : A dithiol that is propane-1,2-dithiol in which one of the methyl hydrogens is replaced by a hydroxy group. a chelating agent originally developed during World War II as an experimental antidote against the arsenic-based poison gas Lewisite, it has been used clinically since 1949 for the treatment of poisoning by arsenic, mercury and gold. It can also be used for treatment of poisoning by antimony, bismuth and possibly thallium, and (with sodium calcium edetate) in cases of acute leaad poisoning. Administration is by (painful) intramuscular injection of a suspension of dimercaprol in peanut oil, typically every 4 hours for 2-10 days depending on the toxicity. In the past, dimercaprol was also used for the treatment of Wilson's disease, a severely debilitating genetic disorder in which the body tends to retain copper, with resultant liver and brain injury.		1.9610dithiol;
primary alcohol		chelator
lysine
Lysine: An essential amino acid. It is often added to animal feed.. lysine : A diamino acid that is caproic (hexanoic) acid bearing two amino substituents at positions 2 and 6.. L-lysine : An L-alpha-amino acid; the L-isomer of lysine.		1.9810aspartate family amino acid;
L-alpha-amino acid zwitterion;
L-alpha-amino acid;
lysine;
organic molecular entity;
proteinogenic amino acid		algal metabolite;
anticonvulsant;
Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
Saccharomyces cerevisiae metabolite
methionine
Methionine: A sulfur-containing essential L-amino acid that is important in many body functions.. methionine : A sulfur-containing amino acid that is butyric acid bearing an amino substituent at position 2 and a methylthio substituent at position 4.		2.1710aspartate family amino acid;
L-alpha-amino acid;
methionine zwitterion;
methionine;
proteinogenic amino acid		antidote to paracetamol poisoning;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical
methanesulfonic acid
[no description available]		2.1710alkanesulfonic acid;
one-carbon compound		Escherichia coli metabolite
malondialdehyde
Malondialdehyde: The dialdehyde of malonic acid.. malonaldehyde : A dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form.		1.9810dialdehydebiomarker
selenomethionine
[no description available]		2.5120selenoamino acid;
selenomethionines		plant metabolite
1-(9-fluorenyl)methyl chloroformate
1-(9-fluorenyl)methyl chloroformate: used for tagging silica-based derivatization reagents in HPLC		2.110
cefmetazole
Cefmetazole: A semisynthetic cephamycin antibiotic with a broad spectrum of activity against both gram-positive and gram-negative microorganisms. It has a high rate of efficacy in many types of infection and to date no severe side effects have been noted.. cefmetazole : A second-generation cephalosporin antibiotic having N(1)-methyltetrazol-5-ylthiomethyl, {[(cyanomethyl)sulfanyl]acetyl}amino and methoxy side-groups at positions 3, 7beta and 7alpha respectively of the parent cephem bicyclic structure.		1.9610cephalosporinantibacterial drug
selenomethylselenocysteine
selenomethylselenocysteine: RN given refers to parent cpd		2.0610non-proteinogenic alpha-amino acid;
selenocysteines		antineoplastic agent;
human metabolite
canavanine
L-canavanine : A non-proteinogenic L-alpha-amino acid that is L-homoserine substituted at oxygen with a guanidino (carbamimidamido) group. Although structurally related to L-arginine, it is non-proteinogenic.		2.1110amino acid zwitterion;
non-proteinogenic L-alpha-amino acid		phytogenic insecticide;
plant metabolite
6-aminoquinolyl-n-hydroxysuccinimidyl carbamate
6-aminoquinolyl-N-hydroxysuccinimidyl carbamate: structure given in first source		2.2510
diethyl maleate
diethyl maleate : A maleate ester resulting from the formal condensation of both carboxy groups of maleic acid with ethanol. A colourless liquid at room temperature (m.p. -10degreeC) with boiling point 220degreeC at 1 atm., it is commonly used as a dienophile for Diels-Alder-type cycloaddition reactions in organic synthesis.		1.9610ethyl ester;
maleate ester		glutathione depleting agent
cysteine
Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.		2.0610cysteiniumfundamental metabolite
selenocysteine
Selenocysteine: A naturally occurring amino acid in both eukaryotic and prokaryotic organisms. It is found in tRNAs and in the catalytic site of some enzymes. The genes for glutathione peroxidase and formate dehydrogenase contain the TGA codon, which codes for this amino acid.. selenocysteine : An alpha-amino acid that consists of alanine where one of the methyl hydrogens is substituted with a seleno group.		2.0610
muramidase
Muramidase: A basic enzyme that is present in saliva, tears, egg white, and many animal fluids. It functions as an antibacterial agent. The enzyme catalyzes the hydrolysis of 1,4-beta-linkages between N-acetylmuramic acid and N-acetyl-D-glucosamine residues in peptidoglycan and between N-acetyl-D-glucosamine residues in chitodextrin. EC 3.2.1.17.		1.9610
ConditionIndicatedRelationship StrengthStudiesTrials
Sensitivity and Specificity
Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)		02.4720