Conditions | Yield |
---|---|
for 2h; Reflux; | 100% |
at 90℃; for 10h; | 68% |
at 90 - 160℃; |
[2-(Methoxycarbonyl-hydrazono)-propyl]-phosphonic acid diethyl ester
Diethyl (2-oxopropyl)phosphonate
Conditions | Yield |
---|---|
With hydrogenchloride; acetone for 3h; Ambient temperature; | 94% |
phosphonic acid diethyl ester
1-bromoacetone
Diethyl (2-oxopropyl)phosphonate
Conditions | Yield |
---|---|
With C30H36B10CuO4P2; potassium carbonate at 20℃; for 7h; Time; Reagent/catalyst; | 93% |
Diethyl (2-oxopropyl)phosphonate
Conditions | Yield |
---|---|
With dipotassium peroxodisulfate; silver(I) acetate In water; N,N-dimethyl-formamide at 85℃; for 24h; Inert atmosphere; Schlenk technique; chemoselective reaction; | 91% |
diethyl (2-methylallyl)phosphonate
Diethyl (2-oxopropyl)phosphonate
Conditions | Yield |
---|---|
With dimethylsulfide; ozone In dichloromethane Oxidation; | 88% |
acetic acid methyl ester
Diethyl methylphosphonate
Diethyl (2-oxopropyl)phosphonate
Conditions | Yield |
---|---|
With lithium diisopropyl amide In tetrahydrofuran at 0℃; for 4.5h; | 87% |
With n-butyllithium In tetrahydrofuran at -78 - 20℃; |
Conditions | Yield |
---|---|
Stage #1: chloroacetone With potassium iodide In acetone at 20℃; for 2h; Stage #2: triethyl phosphite In diethyl ether; acetone for 2h; Reflux; | 85% |
With potassium iodide In acetone; acetonitrile at 20 - 50℃; for 10h; | 83% |
With sodium iodide In acetonitrile at 20℃; | 51% |
diethyl 1-methylthio-2-oxo-n-propylphosphonate
Diethyl (2-oxopropyl)phosphonate
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In toluene for 1h; Heating; | 81% |
Diethyl (2-oxopropyl)phosphonate
Conditions | Yield |
---|---|
With oxalic acid; silica gel In dichloromethane for 1h; Ambient temperature; | 80% |
Conditions | Yield |
---|---|
With hydrogenchloride; water; oxygen; palladium dichloride at 85℃; for 20h; | 80% |
Conditions | Yield |
---|---|
With n-butyllithium; lithium diisopropyl amide In tetrahydrofuran; hexane at -60℃; | 78% |
N-Acetylimidazole
diethylphosphonoacetic acid
Diethyl (2-oxopropyl)phosphonate
Conditions | Yield |
---|---|
With triethylamine; magnesium chloride In acetonitrile at 20℃; for 24h; Acylation; | 77% |
phosphonic acid diethyl ester
acetylacetone
Diethyl (2-oxopropyl)phosphonate
Conditions | Yield |
---|---|
With dipotassium peroxodisulfate; silver(I) acetate In water; N,N-dimethyl-formamide at 85℃; for 24h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; Schlenk technique; chemoselective reaction; | 76% |
Conditions | Yield |
---|---|
In diethyl ether Arbuzov reaction; | 75% |
E-1-Methyl-3-oxo-1-pentenylphosphonsaeurediethylester
A
Diethyl (2-oxopropyl)phosphonate
Conditions | Yield |
---|---|
With dihydrogen peroxide; sodium carbonate In methanol; water for 30h; Ambient temperature; | A 6.9% B 74% |
E-1-Methyl-3-oxo-1-butenylphosphonsaeurediethylester
A
Diethyl (2-oxopropyl)phosphonate
Conditions | Yield |
---|---|
With dihydrogen peroxide; sodium carbonate In methanol; water at 20℃; for 48h; | A 8.2% B 72% |
Conditions | Yield |
---|---|
With dipotassium peroxodisulfate; silver(I) acetate In water at 85℃; Inert atmosphere; Schlenk technique; chemoselective reaction; | 72% |
chloroacetone
triethyl phosphite
A
Diethyl (2-oxopropyl)phosphonate
B
phosphoric acid diethyl ester isopropenyl ester
Conditions | Yield |
---|---|
With potassium iodide In acetone; acetonitrile at 0℃; for 12h; Michaelis-Arbuzov reaction; | A 70% B n/a |
2-methyl-2-phenylsulphonyloxirane
phosphonic acid diethyl ester
Diethyl (2-oxopropyl)phosphonate
Conditions | Yield |
---|---|
other substituted arylsulfonyl epoxides; multistep reaction: synthesis of β-keto phosphonates; | 70% |
With sodium hydride 1) THF, mineral oil, rt, 10 min, 2) THF, rt, 30 min; Yield given. Multistep reaction; |
-butyl vinyl ether
diethyl 1-methylthio-2-oxo-n-propylphosphonate
A
Diethyl (2-oxopropyl)phosphonate
Conditions | Yield |
---|---|
With n-butyl tin hydride; 2,2'-azobis(isobutyronitrile) In toluene for 1h; Heating; Yields of byproduct given; | A n/a B 70% C n/a |
With n-butyl tin hydride; 2,2'-azobis(isobutyronitrile) In toluene for 1h; Heating; Yields of byproduct given; | A n/a B n/a C 37% |
ethyl acetoacetate
phosphonic acid diethyl ester
Diethyl (2-oxopropyl)phosphonate
Conditions | Yield |
---|---|
With dipotassium peroxodisulfate; silver(I) acetate In water; N,N-dimethyl-formamide at 85℃; for 24h; Inert atmosphere; Schlenk technique; chemoselective reaction; | 70% |
phosphonic acid diethyl ester
N,N-diethyl-3-oxobutanamide
Diethyl (2-oxopropyl)phosphonate
Conditions | Yield |
---|---|
With dipotassium peroxodisulfate; silver(I) acetate In water; N,N-dimethyl-formamide at 85℃; for 24h; Inert atmosphere; Schlenk technique; chemoselective reaction; | 66% |
methyllithium
2-(diethoxyphosphinyl)-2-fluoro-acetic acid chloride
A
Diethyl (2-oxopropyl)phosphonate
B
diethyl (1-fluoro-2-oxopropyl)phosphonate
Conditions | Yield |
---|---|
With copper(l) iodide; dimethylsulfide In tetrahydrofuran; diethyl ether 1.) from -78 deg C to -45 deg C; 2.) -45 deg C, 2.5 h; | A 20% B 62% |
2-(diethoxyphosphinyl)-2-fluoro-acetic acid chloride
A
Diethyl (2-oxopropyl)phosphonate
B
diethyl (1-fluoro-2-oxopropyl)phosphonate
Conditions | Yield |
---|---|
at -78 - -45℃; for 3h; | A 20% B 62% |
N,N-Dimethylacetoacetamid
phosphonic acid diethyl ester
Diethyl (2-oxopropyl)phosphonate
Conditions | Yield |
---|---|
With dipotassium peroxodisulfate; silver(I) acetate In water; N,N-dimethyl-formamide at 85℃; for 24h; Inert atmosphere; Schlenk technique; chemoselective reaction; | 62% |
benzyl acetoacetate
phosphonic acid diethyl ester
Diethyl (2-oxopropyl)phosphonate
Conditions | Yield |
---|---|
With dipotassium peroxodisulfate; silver(I) acetate In water; N,N-dimethyl-formamide at 85℃; for 24h; Inert atmosphere; Schlenk technique; chemoselective reaction; | 60% |
phosphonic acid diethyl ester
acetylacetone
A
Diethyl (2-oxopropyl)phosphonate
Conditions | Yield |
---|---|
With dipotassium peroxodisulfate; silver(I) acetate In water; N,N-dimethyl-formamide at 85℃; for 4h; Time; Inert atmosphere; Schlenk technique; chemoselective reaction; | A 58% B 20% |
With dipotassium peroxodisulfate; silver(I) acetate In water; N,N-dimethyl-formamide at 85℃; for 0.5h; Time; Inert atmosphere; Schlenk technique; chemoselective reaction; | A 23% B 53% |
diethyl (2-chloro-2-oxoethyl)phosphonate
methyllithium
Diethyl (2-oxopropyl)phosphonate
Conditions | Yield |
---|---|
With copper(l) iodide; dimethylsulfide In tetrahydrofuran; diethyl ether 1.) from -78 deg C to -45 deg C; 2.) -45 deg C, 2.5 h; | 55% |
diethyl (2-chloro-2-oxoethyl)phosphonate
Diethyl (2-oxopropyl)phosphonate
Conditions | Yield |
---|---|
In tetrahydrofuran; diethyl ether -78 deg C to -40 deg C; -40 deg C, 90 min; | 55% |
Diethyl (2-oxopropyl)phosphonate
Conditions | Yield |
---|---|
With diethylamino-sulfur trifluoride In dichloromethane at -84 - 20℃; for 4h; | 51% |
Conditions | Yield |
---|---|
With potassium carbonate In water at 20℃; for 15h; | 100% |
With potassium carbonate In water at 20℃; for 18h; | 100% |
With potassium carbonate In water at 20℃; for 18h; other aldehyde; | 100% |
Diethyl (2-oxopropyl)phosphonate
(4-methoxyphenoxy)acetaldehyde
Conditions | Yield |
---|---|
With potassium carbonate In water at 0 - 20℃; for 1h; Wadsworth-Emmonds-Horner reaction; | 100% |
3-phenyl-propionaldehyde
Diethyl (2-oxopropyl)phosphonate
(E)-6-phenyl-3-hexen-2-one
Conditions | Yield |
---|---|
Stage #1: Diethyl (2-oxopropyl)phosphonate With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride In acetonitrile at 23℃; for 0.25h; Horner-Wadsworth-Emmons Olefination; Inert atmosphere; Stage #2: 3-phenyl-propionaldehyde In acetonitrile at 0 - 23℃; for 0.5h; Inert atmosphere; | 99% |
With lithium hydroxide monohydrate In tetrahydrofuran at 0℃; for 2h; | 85% |
Stage #1: Diethyl (2-oxopropyl)phosphonate With sodium hydride In tetrahydrofuran for 0.0833333h; Stage #2: 3-phenyl-propionaldehyde In tetrahydrofuran | 82% |
Diethyl (2-oxopropyl)phosphonate
3-Benzyloxypropanal
(E)-6-(benzyloxy)hex-3-en-2-one
Conditions | Yield |
---|---|
With caesium carbonate In 1,4-dioxane; water at 20℃; for 3h; Inert atmosphere; | 99% |
With lithium hydroxide In tetrahydrofuran at 0 - 23℃; Horner-Wadsworth-Emmons reaction; |
Diethyl (2-oxopropyl)phosphonate
4-bromo-benzaldehyde
(E)-4-(4-bromophenyl)but-3-ene-2-one
Conditions | Yield |
---|---|
With caesium carbonate In 1,4-dioxane; water at 20℃; for 3h; Inert atmosphere; | 99% |
Stage #1: Diethyl (2-oxopropyl)phosphonate With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: 4-bromo-benzaldehyde In tetrahydrofuran at 0℃; for 2h; Horner-Emmons reaction; | 81% |
With lithium hydroxide In tetrahydrofuran at 0 - 23℃; Horner-Wadsworth-Emmons reaction; | |
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran Horner-Emmons reaction; |
pyridine-4-carbaldehyde
Diethyl (2-oxopropyl)phosphonate
4-(pyridin-4-yl)-3-buten-2-one
Conditions | Yield |
---|---|
With caesium carbonate In 1,4-dioxane; water at 20℃; for 3h; Inert atmosphere; | 99% |
Diethyl (2-oxopropyl)phosphonate
Conditions | Yield |
---|---|
With RuCl2((R)-binap)(dmf)n; hydrogen In methanol at 50℃; under 3040 Torr; for 50h; | 98% |
With baker's yeast In water at 28 - 30℃; for 120h; | 78% |
With Geotrichum candidum IFO 4597 In water; isopropyl alcohol at 30℃; for 96h; | 72% |
With (R)-TriMe-NAPhePHOS; hydrogen bromide; hydrogen; [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II) In ethanol at 50℃; under 7500.6 Torr; for 24h; | |
With Rhodotorula rubra; chloroacetic acid ethyl ester |
Diethyl (2-oxopropyl)phosphonate
Ethyl-{5-[3-formyl-1-(tetrahydro-pyran-2-yl)-1H-indazol-5-yl]-4-methyl-pyridin-3-ylmethyl}-carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran; water at 20℃; for 20h; | 98% |
Diethyl (2-oxopropyl)phosphonate
diethyl (1-diazo-2-oxopropyl)phosphonate
Conditions | Yield |
---|---|
With 4-toluenesulfonyl azide; triethylamine In acetonitrile Inert atmosphere; | 97% |
With 4-acetamidobenzenesulfonyl azide; triethylamine In acetonitrile at 0 - 20℃; | 95% |
With 4-toluenesulfonyl azide; sodium hydride In tetrahydrofuran | 91% |
Diethyl (2-oxopropyl)phosphonate
4-(14-bromo-tetradec-2-ynyloxymethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
4-[17-(diethoxy-phosphoryl)-16-oxo-heptadec-2-ynyloxymethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
Conditions | Yield |
---|---|
Stage #1: Diethyl (2-oxopropyl)phosphonate With n-butyllithium; sodium hydride In tetrahydrofuran at -78℃; Stage #2: 4-(14-bromo-tetradec-2-ynyloxymethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester In tetrahydrofuran Further stages.; | 97% |
Diethyl (2-oxopropyl)phosphonate
4-methoxy-benzaldehyde
4-(4-methoxyphenyl)-3-buten-2-one
Conditions | Yield |
---|---|
With caesium carbonate In 1,4-dioxane; water at 20℃; for 16h; Inert atmosphere; | 97% |
With lithium hydroxide In tetrahydrofuran at 0 - 23℃; Horner-Wadsworth-Emmons reaction; |
Diethyl (2-oxopropyl)phosphonate
m-tolyl aldehyde
(E)-4-(m-tolyl)but-3-en-2-one
Conditions | Yield |
---|---|
With caesium carbonate In 1,4-dioxane; water at 20℃; for 3h; Inert atmosphere; | 97% |
With potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene at 20℃; for 2h; Inert atmosphere; |
Diethyl (2-oxopropyl)phosphonate
2-Phenylpropanal
5-phenyl-3-hexene-2-one
Conditions | Yield |
---|---|
barium dihydroxide In 1,4-dioxane at 70℃; for 0.166667h; Product distribution; further method; further 2-oxoalkanephosphonates; | 96% |
barium dihydroxide In 1,4-dioxane at 70℃; for 0.166667h; | 96% |
Diethyl (2-oxopropyl)phosphonate
(+/-)-3,3-dimethyl-2-phenylbutanal
Conditions | Yield |
---|---|
barium dihydroxide In 1,4-dioxane at 70℃; for 0.25h; | 96% |
Diethyl (2-oxopropyl)phosphonate
hept-2-ynal
trans-3-decen-5-yn-2-one
Conditions | Yield |
---|---|
With potassium carbonate In water | 96% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In acetonitrile for 24h; Biginelli Pyrimidone Synthesis; Reflux; | 96% |
With zinc trifluoromethanesulfonate In toluene for 3h; Reflux; Green chemistry; | 86% |
ytterbium trifluoromethanesulfonate In toluene for 12h; Heating; | 58% |
Diethyl (2-oxopropyl)phosphonate
(R,S)-Diethyl-(2-hydroxypropyl)phosphonat
Conditions | Yield |
---|---|
With sodium tetrahydroborate In ethanol at 0℃; | 95% |
With pyridine; sodium tetrahydroborate In ethanol 1.) -30 deg C, 10 min, 2.) r.t., 45 min; | 89% |
With diethyl ether Irradiation; | |
With sodium tetrahydroborate In ethanol for 2h; Reduction; | |
With sodium tetrahydroborate In methanol at 0 - 20℃; |
Diethyl (2-oxopropyl)phosphonate
N,N-dimethyl-formamide dimethyl acetal
diethoxyphosphinyl-3 N,N-dimethylamino-4 butene-3 one-2
Conditions | Yield |
---|---|
With calcium chloride for 2h; Heating; | 95% |
Diethyl (2-oxopropyl)phosphonate
N-butylamine
N-[(1-methyl-2-diethoxyphosphoryl)ethyl]-N-n-butylamine
Conditions | Yield |
---|---|
With hydrogenchloride; sodium cyanoborohydride In methanol for 4h; Ambient temperature; | 95% |
Conditions | Yield |
---|---|
at 130℃; for 8h; | 95% |
Diethyl (2-oxopropyl)phosphonate
4-acetamidobenzenesulfonyl azide
diethyl (1-diazo-2-oxopropyl)phosphonate
Conditions | Yield |
---|---|
With triethylamine In acetonitrile at 0 - 20℃; Inert atmosphere; | 95% |
Diethyl (2-oxopropyl)phosphonate
ethyl (phenylhydrazono)chloroacetate
5-methyl-1-phenyl-1H-pyrazole-3-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With lithium hydroxide In 1,2-dimethoxyethane at 20℃; for 10h; regioselective reaction; | 95% |
With lithium hydroxide In 1,2-dimethoxyethane at 20℃; for 10h; regioselective reaction; | 95% |
With lithium hydroxide In 1,2-dimethoxyethane at 20℃; for 10h; |
Conditions | Yield |
---|---|
With sodium hydride | 94% |
2-Ethylbutyraldehyde
Diethyl (2-oxopropyl)phosphonate
5-ethyl-hept-3-en-2-one
Conditions | Yield |
---|---|
With potassium carbonate In water at 100℃; for 0.166667h; | 93% |
Diethyl (2-oxopropyl)phosphonate
α-diethoxyphosphoryl-α,α-dichloroacetone
Conditions | Yield |
---|---|
With sulfuryl dichloride In dichloromethane for 2h; | 93% |
With chlorine In tetrachloromethane at 0℃; for 2h; | 93% |
Conditions | Yield |
---|---|
With indium In tetrahydrofuran at 20℃; for 0.583333h; | 93% |
With zinc 1.) THF, room temperature, 2.) THF, -78 deg C, 30 min; Yield given; Multistep reaction; |
Diethyl (2-oxopropyl)phosphonate
8,8-dimethyl-2-methylene-6-oxabicyclo[3.2.1]octan-7-ol
1-(8,8-dimethyl-2-methylene-6-oxabicyclo[3.2.1]oct-7-yl)acetone
Conditions | Yield |
---|---|
Stage #1: Diethyl (2-oxopropyl)phosphonate With barium dihydroxide at 140℃; for 2h; Stage #2: 3-hydroxy-2,2-dimethyl-6-methylenecyclohexanecarbaldehyde; 8,8-dimethyl-2-methylene-6-oxabicyclo[3.2.1]octan-7-ol In tetrahydrofuran; water at 20℃; for 30h; Further stages.; | 92% |
Molecule structure of Phosphonic acid,P-(2-oxopropyl)-, diethyl ester (CAS NO.1067-71-6):
IUPAC Name: 1-Diethoxyphosphorylpropan-2-one
Molecular Weight: 194.165361 [g/mol]
Molecular Formula: C7H15O4P
Index of Refraction: 1.417
Molar Refractivity: 44.87 cm3
Molar Volume: 178 cm3
Surface Tension: 33.1 dyne/cm
Density: 1.09 g/cm3
Flash Point: 126.9 °C
Enthalpy of Vaporization: 50.09 kJ/mol
Melting Point: 126 °C at 9 mm Hg(lit.)
Boiling Point: 263.1 °C at 760 mmHg
Vapour Pressure: 0.0105 mmHg at 25 °C
H-Bond Acceptor: 4
Rotatable Bond Count: 6
Tautomer Count: 3
Exact Mass: 194.070795
MonoIsotopic Mass: 194.070795
Topological Polar Surface Area: 52.6
Heavy Atom Count: 12
Canonical SMILES: CCOP(=O)(CC(=O)C)OCC
InChI: InChI=1S/C7H15O4P/c1-4-10-12(9,11-5-2)6-7(3)8/h4-6H2,1-3H3
InChIKey: RSAFKRSMGOSHRK-UHFFFAOYSA-N
Product Categories: C-C Bond Formation; Horner-Wadsworth-Emmons Reagents; Olefination
Safety Statements: 24/25
S24/25:Avoid contact with skin and eyes.
WGK Germany: 3
Phosphonic acid,P-(2-oxopropyl)-, diethyl ester (CAS NO.1067-71-6) is also called Diethyl acetonylphosphonate ; Diethyl (2-oxopropyl)phosphonate ; (2-Oxo-propyl)-phosphonicaciddiethylester .
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