Conditions | Yield |
---|---|
With boron trifluoride at 65℃; for 0.333333h; | 100% |
With toluene-4-sulfonic acid In chloroform Heating; | 94% |
With sulfuric acid for 2h; Heating; | 90% |
α-ketoglutaric acid
dimethyl 2-ketoglutarate
Conditions | Yield |
---|---|
In methanol; benzene for 0.5h; Ambient temperature; | 85% |
methanol
α-ketoglutaric acid
A
dimethyl 2-ketoglutarate
B
2-Oxoglutarsaeure-1-methylester
Conditions | Yield |
---|---|
With 2,2-dimethoxy-propane for 144h; Ambient temperature; | A 81% B 7% |
diazomethane
α-ketoglutaric acid
dimethyl 2-ketoglutarate
Conditions | Yield |
---|---|
In diethyl ether at 0℃; for 4h; | 76% |
dimethyl 2-ketoglutarate
Conditions | Yield |
---|---|
With pyridine In tetrahydrofuran; water at 60℃; | 28% |
dimethyl 2-ketoglutarate
Conditions | Yield |
---|---|
With pyridine In tetrahydrofuran; water at 60℃; | 22% |
2,5-dimethoxy-2,5-dihydro-furan-2-carboxylic acid methyl ester
A
4-oxobutanoic acid methyl ester
B
dimethyl 2-ketoglutarate
Conditions | Yield |
---|---|
With hydrogenchloride at 90℃; Erwaermen des Reaktionsprodukts mit Schwefelsaeure enthaltendem Methanol.; |
dimethyl 2-ketoglutarate
Conditions | Yield |
---|---|
With hydrogenchloride |
dimethyl 2-ketoglutarate
Conditions | Yield |
---|---|
at 360℃; |
dimethyl 2-ketoglutarate
Conditions | Yield |
---|---|
at 360℃; |
N-(1-Methoxy-5,5-dimethyl-3-oxocyclohex-1-yl)benzamid
A
dimethyl 2-ketoglutarate
B
benzamide
Conditions | Yield |
---|---|
With hydrogenchloride; ozone 1.) methylenechlorid, -60 deg C; 2.) methanol, room temp, 90 min.; Yield given. Multistep reaction. Yields of byproduct given; |
1,3-dicarbomethoxy-1-(trimethylsilyloxy)propene
dimethyl 2-ketoglutarate
Conditions | Yield |
---|---|
With 1-methoxy-2-(2-nitrovinyl)benzene; tin(IV) chloride other reagents: boron trifluoride etherate/2-methoxy-β-nitrostyrene, benzaldehyde, benzaldehyde, benzaldehyde dimethyl acetal; |
hydrogenchloride
2,5-dimethoxy-2,5-dihydro-furan-2-carboxylic acid methyl ester
A
4-oxobutanoic acid methyl ester
B
dimethyl 2-ketoglutarate
Conditions | Yield |
---|---|
Erwaermen des Reaktionsprodukts mit Methanol und wenig Schwefelsaeure; |
N-(1-Methoxy-5,5-dimethyl-3-oxo-1-cyclohexen-1-yl)benzamid
dimethyl 2-ketoglutarate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 30 percent / H2 / Pd/C / methanol / 48 h 2: 1.) Ozon; 2.) HCl / 1.) methylenechlorid, -60 deg C; 2.) methanol, room temp, 90 min. View Scheme |
2-furoic acid methyl ester
dimethyl 2-ketoglutarate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sulfuric acid / Electrolysis 2: aqueous hydrochloric acid , 35 percent / 90 °C / Erwaermen des Reaktionsprodukts mit Schwefelsaeure enthaltendem Methanol. View Scheme |
dimethyl 2-ketoglutarate
3-bromo-2-oxopentane-1,5-dioic acid dimethyl ester
Conditions | Yield |
---|---|
With copper(ll) bromide In chloroform; ethyl acetate for 18h; Heating; | 100% |
With copper(ll) bromide In chloroform; ethyl acetate at 20℃; Reflux; | 100% |
With copper(ll) bromide In chloroform; ethyl acetate for 18h; Heating; | 90% |
dimethyl 2-ketoglutarate
methyl 6-oxo-1,4,5,6-tetrahydropyridazine-3-carboxylate
Conditions | Yield |
---|---|
With acetic acid; hydrazine In methanol at 70℃; for 18h; | 100% |
With hydrazine hydrate; acetic acid In methanol at 70℃; | 100% |
With acetic acid; hydrazine In methanol for 5h; Reflux; Inert atmosphere; | 100% |
With acetic acid; hydrazine In methanol for 12h; Heating; | 92% |
With acetic acid; hydrazine In methanol Heating; | 92% |
tryptamine
dimethyl 2-ketoglutarate
methyl 2,3,5,6,11,11b-hexahydro-3-oxo-1H-indolizino<8,7-b>indole-11b-carboxylate
Conditions | Yield |
---|---|
With acetic acid for 4h; Reflux; Inert atmosphere; | 97% |
With acetic acid at 120℃; for 3h; Pictet-Spengler reaction; | 86% |
In benzene for 1.5h; Heating; | 58% |
2-(5-methoxyindol-3-yl)ethylamine
dimethyl 2-ketoglutarate
methyl 8-methoxy-2,3,5,6,11,11b-hexahydro-3-oxo-1H-indolizino<8,7-b>indole-11b-carboxylate
Conditions | Yield |
---|---|
With acetic acid for 4h; Reflux; Inert atmosphere; | 97% |
dimethyl 2-ketoglutarate
propargyl bromide
dimethyl 2-H-hydroxy-2-<2-(propynyl)>pentanedioate
Conditions | Yield |
---|---|
With aluminium; mercury dichloride In tetrahydrofuran at -78℃; for 4h; | 95% |
With aluminium; mercury dichloride 1.) 40 deg C, 2.) -78 deg C; Yield given. Multistep reaction; |
dimethyl 2-ketoglutarate
1,2-diamino-benzene
3-(3-oxo-3,4-dihydro-quinoxalin-2-yl)-propionic acid methyl ester
Conditions | Yield |
---|---|
In methanol | 94% |
trimethylsilyl cyanide
dimethyl 2-ketoglutarate
dimethyl 2-cyano-2-(trimethylsilyl)oxyglutarate
Conditions | Yield |
---|---|
for 19h; Ambient temperature; | 93% |
dimethyl 2-ketoglutarate
diisopropyl (E)-azodicarboxylate
Conditions | Yield |
---|---|
With triphenylphosphine In tetrahydrofuran at 20℃; | 93% |
dimethyl 2-ketoglutarate
tryptamine hydochloride
methyl 2,3,5,6,11,11b-hexahydro-3-oxo-1H-indolizino<8,7-b>indole-11b-carboxylate
Conditions | Yield |
---|---|
In methanol for 20h; Heating; | 92% |
In methanol Heating; | 92% |
dimethyl 2-ketoglutarate
ethyl 2-diethoxyphosphorylpropionate
C12H18O6
Conditions | Yield |
---|---|
With hydrogen; sodium hydride In tetrahydrofuran at 0℃; Inert atmosphere; | 91% |
With sodium hydride | 71% |
With sodium hydride Horner-Wadsworth-Emmons Olefination; | 71% |
9-aminothioxanthene 10,10-dioxide
dimethyl 2-ketoglutarate
Conditions | Yield |
---|---|
With 4 A molecular sieve In toluene for 17h; Heating; | 86% |
dimethyl 2-ketoglutarate
propynoic acid methyl ester
Conditions | Yield |
---|---|
triethylamine In dichloromethane at 0℃; | 85% |
With triethylamine In dichloromethane at 0℃; | 85% |
dimethyl 2-ketoglutarate
2-amino-6-(1-benzylhydrazinyl)pyrimidin-4(3H)-one
methyl 3-(7-amino-1-benzyl-4,5-dioxo-1,4,5,6-tetrahydropyrimido[4,5-c]pyridazin-3-yl)propanoate
Conditions | Yield |
---|---|
In water for 3h; Reflux; | 85% |
dimethyl 2-ketoglutarate
1,2-diamino-benzene
methyl 3-(3-oxo-3,4-dihydroquinoxalin-2-yl)propanoate
Conditions | Yield |
---|---|
In methanol for 16h; Inert atmosphere; | 84% |
In ethanol Reflux; |
dimethyl 2-ketoglutarate
dimethyl (E)-2-oxoglutaconate
Conditions | Yield |
---|---|
Stage #1: dimethyl 2-ketoglutarate With bromine In dichloromethane for 4.25h; Heating / reflux; Stage #2: With triethylamine In diethyl ether at 35℃; for 0.75h; | 83.1% |
Stage #1: dimethyl 2-ketoglutarate With bromine In dichloromethane for 3h; Reflux; Inert atmosphere; Stage #2: With triethylamine In diethyl ether at 20℃; for 0.5h; | 70% |
Stage #1: dimethyl 2-ketoglutarate With bromine In dichloromethane for 3h; Heating; Stage #2: With triethylamine In diethyl ether for 0.5h; Further stages.; | 3.6 mmol |
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran for 0.5h; | 82% |
Conditions | Yield |
---|---|
Stage #1: ethyl 2-diethoxyphosphorylpropionate With sodium hydride In tetrahydrofuran for 0.5h; Stage #2: dimethyl 2-ketoglutarate In tetrahydrofuran for 0.5h; | 82% |
ethanol
dimethyl 2-ketoglutarate
(2,4-difluorobenzyl)hydrazine
A
methyl 1-(2,4-difluorobenzyl)-6-oxo-1,4,5,6-tetrahydro-pyridazine-3-carboxylate
B
ethyl 1-(2,4-difluorobenzyl)-6-oxo-1,4,5,6-tetrahydropyridazine-3-carboxylate
Conditions | Yield |
---|---|
hydrogenchloride Reflux; | A 82% B 6.1% |
dimethyl 2-ketoglutarate
benzylamine
methyl 5-(benzylamino)-4,5-dioxopentanoate
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 6h; Inert atmosphere; | 82% |
Conditions | Yield |
---|---|
Stage #1: ethyl 2-diethoxyphosphorylpropionate With sodium hydride In tetrahydrofuran; mineral oil Stage #2: dimethyl 2-ketoglutarate In tetrahydrofuran; mineral oil for 0.5h; | 82% |
dimethyl 2-ketoglutarate
6-methoxytryptamine-2-carboxylic acid
methyl 9-methoxy-2,3,5,6,11,11b-hexahydro-3-oxo-1H-indolizino<8,7-b>indole-11b-carboxylate
Conditions | Yield |
---|---|
With trifluoroacetic acid In 1,4-dioxane; benzene Heating; | 80% |
With trifluoroacetic acid In 1,4-dioxane; benzene for 24h; Heating; | 80% |
dimethyl 2-ketoglutarate
ethyl 2-diethoxyphosphorylpropionate
2-propionic-3-methylmaleic anhydride
Conditions | Yield |
---|---|
Stage #1: dimethyl 2-ketoglutarate; ethyl 2-diethoxyphosphorylpropionate With sodium hydride In tetrahydrofuran for 0.5h; Stage #2: With water; potassium hydroxide In ethanol for 1h; Reflux; | 80% |
dimethyl 2-ketoglutarate
benzylhydrazine dihydrochloride
methyl 1-benzyl-6-oxo-1,4,5,6-tetrahydropyridazine-3-carboxylate
Conditions | Yield |
---|---|
hydrogenchloride In ethanol for 15h; Inert atmosphere; Reflux; | 79% |
dimethyl 2-ketoglutarate
methyl 2-hydroxy-4-(metoxycarbonyl)butanoate
Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol at 0 - 20℃; for 24h; Inert atmosphere; | 78% |
With sodium tetrahydroborate In methanol; dichloromethane for 0.5h; Ambient temperature; | 74% |
With sodium tetrahydroborate | 65% |
With sodium tetrahydroborate In methanol |
dimethyl 2-ketoglutarate
di-isopropyl azodicarboxylate
Conditions | Yield |
---|---|
With 9-phenyl-9-phosphafluorene; Bis(p-nitrophenyl) phosphate; phenylsilane; N-ethyl-N,N-diisopropylamine In toluene at 90℃; for 3.5h; Inert atmosphere; | 76% |
dimethyl 2-ketoglutarate
5-chloro-2-nitrophenylhydrazine
dimethyl (E)-2-(5-chloro-2-nitrophenylhydrazono)glutarate
Conditions | Yield |
---|---|
With hydrogenchloride In methanol at 20℃; for 1h; | 75% |
The Pentanedioic acid,2-oxo-,1,5-dimethyl ester with CAS registry number of 13192-04-6 belongs to the classes of Amino Acids 13C, 2H, 15N; Amino Acids & Derivatives; Miscellaneous Reagents; C6 to C7; Carbonyl Compounds; Esters. The IUPAC name is dimethyl 2-oxopentanedioate. In addition, the molecula formula is C7H10O5 and the molecular weight is 174.15. It is a kind of slight yellow liquid.
Physical properties about this chemical are: (1)ACD/LogP: -0.22; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.21; (4)ACD/LogD (pH 7.4): -0.21; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 18.21; (8)ACD/KOC (pH 7.4): 18.21; (9)#H bond acceptors: 5; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 6; (12)Polar Surface Area: 69.67 Å2; (13)Index of Refraction: 1.427; (14)Molar Refractivity: 38.05 cm3; (15)Molar Volume: 148.1 cm3; (16)Polarizability: 15.08 ×10-24cm3; (17)Surface Tension: 36.8 dyne/cm; (18)Density: 1.175 g/cm3; (19)Flash Point: 105 °C; (20)Enthalpy of Vaporization: 48.66 kJ/mol; (21)Boiling Point: 249.4 °C at 760 mmHg; (22)Vapour Pressure: 0.023 mmHg at 25°C.
Preparation of Pentanedioic acid,2-oxo-,1,5-dimethyl ester: this chemical can be prepared by 2-oxo-pentanedioic acid. This reaction will need solvents methanol and benzene. The reaction time is 30 minutes. The yield is about 85%.
Uses of Pentanedioic acid,2-oxo-,1,5-dimethyl ester: it can react with betrimethyl-silanecarbonitrile to get dimethyl 2-cyano-2-(trimethylsilyl)oxyglutarate. The reaction time is 19 hours at ambient temperature. The yield is about 93%.
You can still convert the following datas into molecular structure:
(1)SMILES: O=C(C(=O)OC)CCC(=O)OC
(2)InChI: InChI=1/C7H10O5/c1-11-6(9)4-3-5(8)7(10)12-2/h3-4H2,1-2H3
(3)InChIKey: TXIXSLPEABAEHP-UHFFFAOYAN
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