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1071-46-1 Usage

Chemical Properties

Yellow liquid

Uses

Different sources of media describe the Uses of 1071-46-1 differently. You can refer to the following data:
1. Ethyl Hydrogen Malonate has been shown to impair brain mitochondrial succinate and malate transport. It is also found in the extract of Hericum erinaceus mushroom which shows antitumor effects in tumo r-bearing mice.
2. Ethyl hydrogen malonate is used as a reactant for the preparation of tetramic acids through Dieckmann ring closure and organocatalytic decarboxylative Doebner-Knoevenagel reactions. It is involved in the acylation reactions and Knoevenagel condensation with aldehydes. It is also used in the preparation of gamma-lactones from olefins by intermolecular carbolactonization in presence of Mn(III) acetate as a catalyst.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 4, p. 417, 1963Tetrahedron Letters, 26, p. 1411, 1985 DOI: 10.1016/S0040-4039(00)99058-0

Check Digit Verification of cas no

The CAS Registry Mumber 1071-46-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,0,7 and 1 respectively; the second part has 2 digits, 4 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 1071-46:
(6*1)+(5*0)+(4*7)+(3*1)+(2*4)+(1*6)=51
51 % 10 = 1
So 1071-46-1 is a valid CAS Registry Number.
InChI:InChI=1/C5H8O4/c1-2-9-5(8)3-4(6)7/h2-3H2,1H3,(H,6,7)

1071-46-1 Well-known Company Product Price

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  • Alfa Aesar

  • (44692)  Ethyl hydrogen malonate, 90+%   

  • 1071-46-1

  • 5g

  • 277.0CNY

  • Detail
  • Alfa Aesar

  • (44692)  Ethyl hydrogen malonate, 90+%   

  • 1071-46-1

  • 25g

  • 1088.0CNY

  • Detail
  • Alfa Aesar

  • (44692)  Ethyl hydrogen malonate, 90+%   

  • 1071-46-1

  • 100g

  • 3506.0CNY

  • Detail
  • Alfa Aesar

  • (44692)  Ethyl hydrogen malonate, 90+%   

  • 1071-46-1

  • 500g

  • 14662.0CNY

  • Detail
  • Alfa Aesar

  • (A12627)  Ethyl hydrogen malonate, 96%   

  • 1071-46-1

  • 10g

  • 507.0CNY

  • Detail
  • Alfa Aesar

  • (A12627)  Ethyl hydrogen malonate, 96%   

  • 1071-46-1

  • 50g

  • 2135.0CNY

  • Detail
  • Alfa Aesar

  • (A12627)  Ethyl hydrogen malonate, 96%   

  • 1071-46-1

  • 250g

  • 5422.0CNY

  • Detail

1071-46-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Ethyl hydrogen malonate

1.2 Other means of identification

Product number -
Other names 3-ethoxy-3-oxapropanoic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1071-46-1 SDS

1071-46-1Synthetic route

ethyl potassium malonate
6148-64-7

ethyl potassium malonate

hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

Conditions
ConditionsYield
With hydrogenchloride In water at 5℃; for 1h;100%
With hydrogenchloride In water at 0℃; for 0.666667h;99%
With hydrogenchloride In water Inert atmosphere; Cooling with ice;91%
diethyl malonate
105-53-3

diethyl malonate

hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water at 25℃; for 1h;94%
With potassium hydroxide In tetrahydrofuran at 0℃; for 1h;90%
Stage #1: diethyl malonate With potassium hydroxide; water In tetrahydrofuran at 0℃; for 1h;
Stage #2: With hydrogenchloride; water In tetrahydrofuran at 0℃; Product distribution / selectivity;
90%
ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

Conditions
ConditionsYield
With potassium phosphate buffer; nitrilase from Alcaligenes faecalis ATCC8750 at 30℃; for 7h; pH=7.3;94%
With benzene-1,2-dicarboxylic acid at 250℃; under 7600 Torr; for 0.25h; microwave irradiation;53%
With benzene-1,2-dicarboxylic acid at 240℃; under 3040 Torr; for 1h;10%
With copper(II) sulfate at 240℃; for 1h;9%
ethanol
64-17-5

ethanol

malonic acid
141-82-2

malonic acid

hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

Conditions
ConditionsYield
With boric acid Heating;80%
With sulfuric acid
With sulfuric acid In acetone for 168h;
With boric acid for 18h; Reflux;
at 80℃;
diethyl malonate
105-53-3

diethyl malonate

A

malonic acid
141-82-2

malonic acid

B

hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

Conditions
ConditionsYield
Stage #1: diethyl malonate With water; potassium hydroxide In tetrahydrofuran at 0℃; for 0.5h;
Stage #2: In tetrahydrofuran; water Acidic conditions;
A 8.3%
B 76.9%
Stage #1: diethyl malonate With water; potassium hydroxide at 0℃; for 6h;
Stage #2: Acidic aq. solution;
A 36.6%
B 35.6%
malonic acid
141-82-2

malonic acid

ethyl acetate
141-78-6

ethyl acetate

hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

Conditions
ConditionsYield
With iron(III) perchlorate for 2h; Ambient temperature;76%
ethyl malonamate
7597-56-0

ethyl malonamate

A

acetamide
60-35-5

acetamide

B

malonic acid
141-82-2

malonic acid

C

hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

D

acetic acid
64-19-7

acetic acid

Conditions
ConditionsYield
With phthalic anhydride at 240 - 250℃; under 3040 Torr; for 1h; Hydrolysis;A n/a
B n/a
C 53%
D n/a
carbon monoxide
201230-82-2

carbon monoxide

ethyl iodoacetae
623-48-3

ethyl iodoacetae

hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

Conditions
ConditionsYield
With dmap; bis-triphenylphosphine-palladium(II) chloride; pyrrole; triethylamine In water; toluene UV-irradiation; Autoclave;52%
malonic acid ethyl ester 2-thioxo-2H-pyridin-1-yl ester

malonic acid ethyl ester 2-thioxo-2H-pyridin-1-yl ester

A

(Ethoxycarbonyl)methyl 2-pyridyl sulfide
28856-92-0

(Ethoxycarbonyl)methyl 2-pyridyl sulfide

B

2,2'-dipyridyldisulphide
2127-03-9

2,2'-dipyridyldisulphide

C

hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

Conditions
ConditionsYield
In benzene photolysis; Irradiation;A 48%
B 3%
C 17%
carbon dioxide
124-38-9

carbon dioxide

ethyl bromoacetate
105-36-2

ethyl bromoacetate

hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

Conditions
ConditionsYield
With tetraethylammonium chloride; silver; magnesium In acetonitrile at 0℃; under 760.051 Torr; Electrolysis;38%
ethyl acetate
141-78-6

ethyl acetate

hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

Conditions
ConditionsYield
With diethyl ether; ammonia; sodium amide nachfolgendes Behandeln mit festem CO2;
With triphenylmethyl sodium at 0℃; nachfolgendes Behandeln mit festem CO2;
ethanol
64-17-5

ethanol

S,S'-diethyl dithiomalonate
16501-24-9

S,S'-diethyl dithiomalonate

hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

Conditions
ConditionsYield
With potassium hydroxide Heating;
ethyl (ethylthio)carbonylacetate
16694-80-7

ethyl (ethylthio)carbonylacetate

hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

Conditions
ConditionsYield
With potassium hydroxide In ethanol Heating;
chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

acetic acid
64-19-7

acetic acid

hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

Conditions
ConditionsYield
(i) LDA, (ii) /BRN= 385653/; Multistep reaction;
cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

ethanol
64-17-5

ethanol

hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

Conditions
ConditionsYield
for 24h; Heating;
In toluene for 2h; Heating; Yield given;
In toluene for 5h; Heating;
diethyl ethylidenemalonate
1462-12-0

diethyl ethylidenemalonate

A

hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

B

2-Eth-(Z)-ylidene-malonic acid monoethyl ester

2-Eth-(Z)-ylidene-malonic acid monoethyl ester

C

2-Eth-(E)-ylidene-malonic acid monoethyl ester

2-Eth-(E)-ylidene-malonic acid monoethyl ester

Conditions
ConditionsYield
With water pH 8;
tert-Butyl ethyl malonate
32864-38-3

tert-Butyl ethyl malonate

hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

Conditions
ConditionsYield
With bromocatecholborane In dichloromethane for 18h; Ambient temperature; Yield given;
carbon dioxide
124-38-9

carbon dioxide

chloroacetic acid ethyl ester
105-39-5

chloroacetic acid ethyl ester

hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

Conditions
ConditionsYield
In tetrahydrofuran at 5℃; electrochemical oxidation;
carbon dioxide
124-38-9

carbon dioxide

ethyl acetate
141-78-6

ethyl acetate

hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

Conditions
ConditionsYield
Reaktion des Natriumenolats;
potassium salt of monoethyl ester

potassium salt of monoethyl ester

hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

Conditions
ConditionsYield
With hydrogenchloride
3,4-dibromo-2-oxo-but-3-ene-1,1,4-tricarboxylic acid-1,1-diethyl ester

3,4-dibromo-2-oxo-but-3-ene-1,1,4-tricarboxylic acid-1,1-diethyl ester

alkali, aqueous

alkali, aqueous

A

dibromomaleic acid
608-37-7

dibromomaleic acid

B

hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

Conditions
ConditionsYield
Erwaermen;
oxo-ethane-1,1,2-tricarboxylic acid triethyl ester
861351-52-2

oxo-ethane-1,1,2-tricarboxylic acid triethyl ester

water
7732-18-5

water

hydrochloric acid , concentrated

hydrochloric acid , concentrated

A

hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

B

oxalic acid
144-62-7

oxalic acid

oxo-ethane-1,1,2-tricarboxylic acid triethyl ester
861351-52-2

oxo-ethane-1,1,2-tricarboxylic acid triethyl ester

water
7732-18-5

water

sulfuric acid , aqueous

sulfuric acid , aqueous

A

hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

B

oxalic acid
144-62-7

oxalic acid

Conditions
ConditionsYield
Erhitzen;
diethyl malonate
105-53-3

diethyl malonate

Me3SiCH2C(Me)=CH(CH2)2CH(Me)-X

Me3SiCH2C(Me)=CH(CH2)2CH(Me)-X

A

hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

B

Na2S2O8

Na2S2O8

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 91 percent / KOH / ethanol / 1 h / Heating
2: 100 percent / HCl / H2O / 1 h / 5 °C
View Scheme
diethyl malonate
105-53-3

diethyl malonate

PhCOCH2-X

PhCOCH2-X

hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 50 percent / KOH / ethanol
2: 55 percent / conc. HCl / H2O
View Scheme
ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl-<3-bromo propionate>

ethyl-<3-bromo propionate>

A

hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

B

sodium hydroxide

sodium hydroxide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (i) HCl, benzene, (ii) H2O
2: KOH / ethanol / Heating
View Scheme
sodium monoethyl malonate
43167-10-8

sodium monoethyl malonate

hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

Conditions
ConditionsYield
With hydrogenchloride; water pH=3;52.2 g
2,4-oxetanedione
15159-48-5

2,4-oxetanedione

ethanol
64-17-5

ethanol

hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

Conditions
ConditionsYield
at -65℃;
hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

phenylacetyl chloride
103-80-0

phenylacetyl chloride

ethyl 3-oxo-4-phenylbutyrate
718-08-1

ethyl 3-oxo-4-phenylbutyrate

Conditions
ConditionsYield
Stage #1: hydrogen ethyl malonate With n-butyllithium In tetrahydrofuran; hexane at -78 - -10℃;
Stage #2: phenylacetyl chloride In tetrahydrofuran; hexane at -78℃; for 0.166667h; Further stages.;
100%
With [2,2]bipyridinyl; n-butyllithium In tetrahydrofuran; hexane at -65℃; for 0.0833333h;85%
75%
hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

tert-butyl alcohol
75-65-0

tert-butyl alcohol

tert-Butyl ethyl malonate
32864-38-3

tert-Butyl ethyl malonate

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In dichloromethane at 25℃; for 0.25h;100%
With dicyclohexyl-carbodiimide In acetonitrile for 2h;66%
With diphenyl phosphoryl azide; triethylamine
With 2-chloro-1-methyl-pyridinium iodide; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 2h;
With dicyclohexyl-carbodiimide In acetonitrile at 25℃; for 1h;
hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

2,4,5-trifluorobenzoyl chloride
88419-56-1

2,4,5-trifluorobenzoyl chloride

ethyl 2,4,5-trifluorobenzoylacetate
98349-24-7

ethyl 2,4,5-trifluorobenzoylacetate

Conditions
ConditionsYield
Stage #1: hydrogen ethyl malonate With n-butyllithium; triphenylmethane In tetrahydrofuran Metallation;
Stage #2: 2,4,5-trifluorobenzoyl chloride In tetrahydrofuran at 20℃; for 1h; Acetylation;
100%
Stage #1: hydrogen ethyl malonate With n-butyllithium In tetrahydrofuran at -75 - -5℃; for 0.0333333h;
Stage #2: 2,4,5-trifluorobenzoyl chloride In tetrahydrofuran at -75 - 20℃;
Stage #3: With hydrogenchloride; water In tetrahydrofuran; ethyl acetate
89%
With n-butyllithium; biquinoline 1.) THF, -30 deg C to - 5 deg C, 2.) -50 deg C, 0.5 h; Yield given. Multistep reaction;
hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

magnesium bis(3-ethoxy-3-oxopropanoate)
37517-78-5

magnesium bis(3-ethoxy-3-oxopropanoate)

Conditions
ConditionsYield
With magnesium(II) chloride hexahydrate; potassium hydroxide In water Cooling with ice;100%
With magnesium In tetrahydrofuran for 4h; Heating / reflux;
With magnesium ethylate In tetrahydrofuran at 20℃; for 2.5h;
hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

(2R)-tetrahydrofuran-2-carboxylic acid chloride
148151-47-7

(2R)-tetrahydrofuran-2-carboxylic acid chloride

ethyl 3-oxo-3-[(2R)-tetrahydrofuran-2-yl]propanoate
1161825-32-6

ethyl 3-oxo-3-[(2R)-tetrahydrofuran-2-yl]propanoate

Conditions
ConditionsYield
Stage #1: hydrogen ethyl malonate With n-butyllithium In tetrahydrofuran; hexanes at -78 - -5℃;
Stage #2: (2R)-tetrahydrofuran-2-carboxylic acid chloride In tetrahydrofuran; hexanes at -65℃; for 1h;
100%
hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

(2S,4R)-1-benzyl 4-methyl 4-amino-2-methylpiperidine-1,4-dicarboxylate
1227685-20-2

(2S,4R)-1-benzyl 4-methyl 4-amino-2-methylpiperidine-1,4-dicarboxylate

1-benzyl 4-methyl (2S,4R)-4-[(3-ethoxy-3-oxopropanoyl)amino]-2-methylpiperidine-1,4-dicarboxylate

1-benzyl 4-methyl (2S,4R)-4-[(3-ethoxy-3-oxopropanoyl)amino]-2-methylpiperidine-1,4-dicarboxylate

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃;100%
hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

m-formylphenyl benzoic acid
619-21-6

m-formylphenyl benzoic acid

(E)-3-(3-ethoxy-3-oxoprop-1-en-1-yl)benzoic acid
91047-79-9

(E)-3-(3-ethoxy-3-oxoprop-1-en-1-yl)benzoic acid

Conditions
ConditionsYield
With piperidine In pyridine at 100℃; for 18h; Inert atmosphere;100%
hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

C20H32N2
1616724-87-8

C20H32N2

C25H38N2O3
1616724-88-9

C25H38N2O3

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0.25℃; for 12h;100%
hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

ethyl 2-((cyclopropylmethyl)amino)benzoate

ethyl 2-((cyclopropylmethyl)amino)benzoate

ethyl 2-(N-(cyclopropylmethyl)-3-ethoxy-3-oxopropanamido)benzoate

ethyl 2-(N-(cyclopropylmethyl)-3-ethoxy-3-oxopropanamido)benzoate

Conditions
ConditionsYield
With pyridine; trichlorophosphate In acetonitrile at 0 - 5℃; for 2h;100%
piperonal
120-57-0

piperonal

hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

ethyl (E)-3-(benzo[d][1,3]dioxol-5-yl)acrylate
24393-66-6

ethyl (E)-3-(benzo[d][1,3]dioxol-5-yl)acrylate

Conditions
ConditionsYield
With poly{styrene-co-[4-(N-methyl-N-vinylbenzyl-amino)pyridine]-co-[1-phenyl-3-(4-vinylbenzyl)piperazine]} In N,N-dimethyl-formamide at 50℃; decarboxylative Doebner-Knoevenagel condensation reaction; optical yield given as %de; stereoselective reaction;99%
With piperidine; pyridine
With piperidine; pyridine at 70℃; for 9h;
hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

(E)-4-(4-Isopropoxy-phenyl)-but-3-en-2-one
70685-50-6

(E)-4-(4-Isopropoxy-phenyl)-but-3-en-2-one

3-Hydroxy-5-(4-isopropoxy-phenyl)-cyclohex-2-enone
111973-93-4

3-Hydroxy-5-(4-isopropoxy-phenyl)-cyclohex-2-enone

Conditions
ConditionsYield
With sodium methylate In methanol99%
hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

isobutyryl chloride
79-30-1

isobutyryl chloride

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran99%
Stage #1: hydrogen ethyl malonate With [2,2]bipyridinyl; n-butyllithium In tetrahydrofuran; hexane at -70 - -10℃; Inert atmosphere;
Stage #2: isobutyryl chloride In tetrahydrofuran; hexane at -65℃; for 0.166667h; Inert atmosphere;
80%
hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

Conditions
ConditionsYield
With dmap In N,N-dimethyl-formamide at 25℃; Doebner-Knoevenagel reaction;99%
With dmap In N,N-dimethyl-formamide at 25℃; Knoevenagel reaction;99%
piperidine; dmap In N,N-dimethyl-formamide at 10 - 20℃; for 24h; Product distribution / selectivity;99%
With poly{styrene-co-[4-(N-methyl-N-vinylbenzyl-amino)pyridine]-co-[1-phenyl-3-(4-vinylbenzyl)piperazine]} In N,N-dimethyl-formamide at 50℃; decarboxylative Doebner-Knoevenagel condensation reaction; optical yield given as %de;97%
thiophene-2-carbaldehyde
98-03-3

thiophene-2-carbaldehyde

hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

ethyl (E)-3-(thiophen-2-yl)acrylate
13979-15-2

ethyl (E)-3-(thiophen-2-yl)acrylate

Conditions
ConditionsYield
With poly{styrene-co-[4-(N-methyl-N-vinylbenzyl-amino)pyridine]-co-[1-phenyl-3-(4-vinylbenzyl)piperazine]} In N,N-dimethyl-formamide at 50℃; decarboxylative Doebner-Knoevenagel condensation reaction; optical yield given as %de; stereoselective reaction;99%
With dmap
hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

glycine ethyl ester hydrochloride
623-33-6

glycine ethyl ester hydrochloride

ethyl 3-((2-ethoxy-2-oxoethyl)amino)-3-oxopropanoate
51925-56-5

ethyl 3-((2-ethoxy-2-oxoethyl)amino)-3-oxopropanoate

Conditions
ConditionsYield
With dmap; triethylamine; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 6.5h; Inert atmosphere;99%
Stage #1: hydrogen ethyl malonate; glycine ethyl ester hydrochloride With dmap; triethylamine In dichloromethane at 0℃; for 0.5h;
Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 7h;
79%
With dicyclohexyl-carbodiimide; trimethylamine In dichloromethane at 0 - 20℃; for 4.5h;78%
With triethylamine; dicyclohexyl-carbodiimide In dichloromethane at 20℃;70%
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

ethyl (E)-3-(pyridin-3-yl)acrylate
59607-99-7, 28447-17-8

ethyl (E)-3-(pyridin-3-yl)acrylate

Conditions
ConditionsYield
With poly{styrene-co-[4-(N-methyl-N-vinylbenzyl-amino)pyridine]-co-[1-phenyl-3-(4-vinylbenzyl)piperazine]} In N,N-dimethyl-formamide at 50℃; decarboxylative Doebner-Knoevenagel condensation reaction; optical yield given as %de; stereoselective reaction;99%
hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

ethyl (E)-3-(4-bromophenyl)-2-propenoate
24393-53-1, 136265-11-7, 15795-20-7

ethyl (E)-3-(4-bromophenyl)-2-propenoate

Conditions
ConditionsYield
With poly{styrene-co-[4-(N-methyl-N-vinylbenzyl-amino)pyridine]-co-[1-phenyl-3-(4-vinylbenzyl)piperazine]} In N,N-dimethyl-formamide at 50℃; decarboxylative Doebner-Knoevenagel condensation reaction; optical yield given as %de; stereoselective reaction;99%
hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

ortho-anisaldehyde
135-02-4

ortho-anisaldehyde

ethyl 3-(2-methoxyphenyl)prop-2-enoate
24393-54-2

ethyl 3-(2-methoxyphenyl)prop-2-enoate

Conditions
ConditionsYield
With poly{styrene-co-[4-(N-methyl-N-vinylbenzyl-amino)pyridine]-co-[1-phenyl-3-(4-vinylbenzyl)piperazine]} In N,N-dimethyl-formamide at 50℃; decarboxylative Doebner-Knoevenagel condensation reaction; optical yield given as %de; stereoselective reaction;99%
hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

N-methylaniline
100-61-8

N-methylaniline

ethyl 3-(N-methyl-N-phenylamino)-3-oxopropionate
59050-15-6

ethyl 3-(N-methyl-N-phenylamino)-3-oxopropionate

Conditions
ConditionsYield
With 2-chloro-1-methyl-pyridinium iodide; triethylamine In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere;99%
With dicyclohexyl-carbodiimide In dichloromethane at 20℃;90%
With 2-chloro-1-methyl-pyridinium iodide; triethylamine In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere;77%
hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

DL-alanine ethyl ester hydrochloride
617-27-6

DL-alanine ethyl ester hydrochloride

N-Aethoxycarbonylacetylsarcosinaethylester

N-Aethoxycarbonylacetylsarcosinaethylester

Conditions
ConditionsYield
With dmap; triethylamine; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 2.5h; Inert atmosphere;99%
hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

vanillin
121-33-5

vanillin

ethyl 4-hydroxy-3-methoxycinnamate
4046-02-0

ethyl 4-hydroxy-3-methoxycinnamate

Conditions
ConditionsYield
Stage #1: hydrogen ethyl malonate; vanillin With piperidine; pyridine at 100℃; for 24h; Knoevenagel Condensation;
Stage #2: With hydrogenchloride In water at -10 - 0℃; for 24h;
98%
With piperidine In pyridine at 100℃; for 8h; Knoevenagel Condensation;97%
With piperidine; pyridine; aniline
With pyridine Knoevenagel Condensation; Reflux;
hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

(S)-N-[1-(5-oxazoyl)ethyl]-1H-indole-3-ethanamine
196819-38-2

(S)-N-[1-(5-oxazoyl)ethyl]-1H-indole-3-ethanamine

(S)-3-[[2-(1H-indol-3-yl)ethyl][1-(5-oxazoyl)ethyl]amino]-3-oxopropanoic acid ethyl ester
196819-50-8

(S)-3-[[2-(1H-indol-3-yl)ethyl][1-(5-oxazoyl)ethyl]amino]-3-oxopropanoic acid ethyl ester

Conditions
ConditionsYield
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide for 2h; Ambient temperature;98%
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide at 20℃; for 2h; Condensation;98%
hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

benzyl chloroformate
501-53-1

benzyl chloroformate

A

benzyl ethyl malonate
42998-51-6

benzyl ethyl malonate

B

CO2

CO2

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 4℃; for 0.5h;A 98%
B n/a
2,2-dimethylbut-3-enoyl chloride
57690-96-7

2,2-dimethylbut-3-enoyl chloride

hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

ethyl 4,4-dimethyl-3-oxo-hex-5-enoate
66248-79-1

ethyl 4,4-dimethyl-3-oxo-hex-5-enoate

Conditions
ConditionsYield
Stage #1: hydrogen ethyl malonate With [2,2]bipyridinyl; n-butyllithium In tetrahydrofuran; hexane at -70 - -10℃;
Stage #2: 2,2-dimethylbut-3-enoyl chloride In tetrahydrofuran; hexane at -60 - 0℃; for 3h;
98%
With n-butyllithium In tetrahydrofuran; hexane at -65℃; for 1h;8.1 g
Stage #1: hydrogen ethyl malonate With n-butyllithium In tetrahydrofuran; hexanes at -70 - -10℃; Inert atmosphere;
Stage #2: 2,2-dimethylbut-3-enoyl chloride In tetrahydrofuran; hexanes at -60 - 0℃; for 3h;
hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

para-acetamidobenzaldehyde
122-85-0

para-acetamidobenzaldehyde

ethyl 3-(4-acetylaminophenyl)-2-propenoate
215258-04-1

ethyl 3-(4-acetylaminophenyl)-2-propenoate

Conditions
ConditionsYield
With poly{styrene-co-[4-(N-methyl-N-vinylbenzyl-amino)pyridine]-co-[1-phenyl-3-(4-vinylbenzyl)piperazine]} In N,N-dimethyl-formamide at 50℃; decarboxylative Doebner-Knoevenagel condensation reaction; optical yield given as %de; stereoselective reaction;98%
With dmap In N,N-dimethyl-formamide at 25℃; for 168h; Knoevenagel reaction;92%
hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

ethyl (+/-)-trans-2-oxo-1,4-diphenyl-azetidine-3-carboxylate

ethyl (+/-)-trans-2-oxo-1,4-diphenyl-azetidine-3-carboxylate

Conditions
ConditionsYield
Stage #1: hydrogen ethyl malonate With 1,1'-carbonyldiimidazole In dichloromethane at 25℃; for 1h;
Stage #2: (E)-N-benzylidenebenzenamine In dichloromethane at 25℃; for 1h;
98%
Stage #1: hydrogen ethyl malonate With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 1h; Staudinger reaction; Inert atmosphere;
Stage #2: (E)-N-benzylidenebenzenamine In dichloromethane at 20℃; for 1h; Staudinger reaction; Inert atmosphere; stereoselective reaction;
79%
hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

ethyl (E)-3-(4-chlorophenyl)prop-2-enoate
24393-52-0

ethyl (E)-3-(4-chlorophenyl)prop-2-enoate

Conditions
ConditionsYield
With poly{styrene-co-[4-(N-methyl-N-vinylbenzyl-amino)pyridine]-co-[1-phenyl-3-(4-vinylbenzyl)piperazine]} In N,N-dimethyl-formamide at 50℃; decarboxylative Doebner-Knoevenagel condensation reaction; optical yield given as %de; stereoselective reaction;98%
With dmap
hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

ethyl 2-(butoxyamino)benzoate

ethyl 2-(butoxyamino)benzoate

ethyl 2-(N-butoxy-3-ethoxy-3-oxopropanamido)benzoate

ethyl 2-(N-butoxy-3-ethoxy-3-oxopropanamido)benzoate

Conditions
ConditionsYield
With pyridine; trichlorophosphate In acetonitrile at 0 - 5℃; for 2h;98%
hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

4-(p-isopropylphenyl)-3-buten-2-one
74389-78-9

4-(p-isopropylphenyl)-3-buten-2-one

3-Hydroxy-5-(4-isopropyl-phenyl)-cyclohex-2-enone
111945-86-9

3-Hydroxy-5-(4-isopropyl-phenyl)-cyclohex-2-enone

Conditions
ConditionsYield
With sodium methylate In methanol97%

1071-46-1Relevant articles and documents

Electrocatalytic carboxylation of aliphatic halides at silver cathode in acetonitrile

Niu, Dong-Fang,Xiao, Li-Ping,Zhang, Ai-Jian,Zhang, Gui-Rong,Tan, Qi-Yun,Lu, Jia-Xing

, p. 10517 - 10520 (2008)

A simple and efficient electrocarboxylation reaction of aliphatic halides has been developed using silver as cathode, magnesium as anode and CH3CN saturated CO2 as solvent in an undivided cell. The influence of some key factors (such as the nature of electrode materials, supporting electrolytes and temperature) on this reaction was investigated. Under the optimized condition, the corresponding carboxylic acids were obtained in moderate to good yields (22-89%). The electrochemical behaviour was studied at different electrodes (Ag, Cu, Ni and Ti) by cyclic voltammetry, which showed significant electrocatalytic effect of the silver electrode towards the reductive carboxylation of aliphatic halides.

ALKYLIMINOMALONIC ACID AND 2-ALKYLOXAZIRIDINE-3,3-DICARBOXYLIC ACID ESTERS

Prosyanik, A.V.,Moskalenko, A.S.,Moretti, J.,Forni, A.,Torre, G.,Kostyanovskii, R.G.

, p. 431 - 437 (1986)

2-Alkyloxaziridine-3,3-dicarboxylic acid esters have been obtained by oxidizing alkylaminomalonic acid ester by monoperphtalic acid.The activation parameters for the inversion of the nitrogen atom have been obtained for a number of alkyliminomalonic acid and 2-alkyloxaziridine-3,3-dicarboxylic acid ester.

Highly efficient selective monohydrolysis of dialkyl malonates and their derivatives

Niwayama, Satomi,Cho, Hanjoung,Lin, Chunlei

, p. 4434 - 4436 (2008)

The highly efficient selective monohydrolysis of symmetric diesters has been applied to monohydrolysis of several dialkyl malonates and their derivatives. The best conditions apply 0.8-1.2 equiv of aqueous KOH with a co-solvent, THF or acetonitrile, at 0 °C. The procedure is highly practical, yielding the corresponding half-esters in high yields in a straightforward manner, without inducing decarboxylation. It was found that the selectivity tends to become higher with increased hydrophobicity.

Synthesis of diverse N, O-bridged calix[1]arene[4]pyridine-C60 dyads and triads and formation of intramolecular self-inclusion complexes

Wu, Jin-Cheng,Wang, De-Xian,Huang, Zhi-Tang,Wang, Mei-Xiang

, p. 8604 - 8614 (2010)

Starting from both the bridging nitrogen atom-functionalized and the upper rim-functionalized N,O-bridged calix[1]arene[4]pyridine reactants, different types of heteracalixaromatics-C60 dyads and triads of varied spacers were expediently synthesized using mainly the click reaction as the key step. By means of various spectroscopic methods, the heteracalixaromatics-C60 dyads and triads obtained have been shown to form intramolecular self-inclusion complexes rather than oligomers or polymers in solution because of a flexible spacer in between the heteracalixaromatic ring and C60 moiety. The current study, coupled with previous investigations, would provide the guideline for the construction of supramolecular fullerene motifs based on molecular design of the dyads and triads.

Selective monoesterification of malonic acid catalyzed by boric acid

Levonis, Stephan M.,Bornaghi, Laurent F.,Houston, Todd A.

, p. 821 - 823 (2007)

Boric acid catalyzes the monoesterification of malonic acid, likely through a chelation mechanism that is not available to the monoester product. Under more forcing conditions, diesters form to some extent, but conditions can be optimized to favour the monoester product (56?80%). With the easily handled solid acid catalyst, these reactions can be run with excess alcohol as solvent or with stoichiometric amounts of alcohol in acetonitrile with moderate heating. CSIRO 2007.

-

Breslow,Baumgarten,Hauser

, p. 1286 (1944)

-

A stereocontrolled total synthesis of (±)-saframycin A

Kimura, Shinya,Saito, Naoki

, p. 4504 - 4514 (2018/07/21)

A thirteen-step total synthesis of (±)-saframycin A from a tricyclic lactam intermediate is described. The key step of this total synthesis is the stereocontrolled construction of a pentacyclic saframycin framework via a modified Pictet-Spengler type cyclization generating a bis-carboxylic acid ester derivative, followed by decarboxylation. The cytotoxicity profiles are also presented.

Development of catalytic deacylative alkylations (DaA) of 3-acyl-2-oxindoles: total synthesis of meso-chimonanthine and related alkaloids

Kumar, Nivesh,Das, Mrinal Kanti,Ghosh, Santanu,Bisai, Alakesh

supporting information, p. 2170 - 2173 (2017/02/19)

We present an effective deacylative alkylation strategy for the construction of a variety of 2-oxindoles bearing an all-carbon quaternary center at the pseudobenzylic position. A wide variety of products with quaternary centers could be accessed by employing simple Pd(0) catalysis under mild reaction conditions. Importantly, the same strategy works equally well for the dimeric 2-oxindole system, furnishing products with a vicinal quaternary center in favour of meso-isomer as the major product. Eventual application to the total syntheses of meso-chimonanthine and meso-folicanthine very well demonstrates the synthetic potential of this strategy.

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