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114-76-1

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114-76-1 Usage

Uses

Different sources of media describe the Uses of 114-76-1 differently. You can refer to the following data:
1. Sodium phenylpyruvate is a substrate for phenylpyruvate decarboxylase and phenylpyruvate tautomerase.It inhibits amino acid formation and depresses oxygen consumption.
2. Phenylpyruvic acid, sodium salt is a substrate for phenylpyruvate decarboxylase and phenylpyruvate tautomerase.

Biological Activity

Sodium phenylpyruvate (Phenylpyruvic acid sodium salt) inhibits amino acid formation and depresses oxygen consumption.

Enzyme inhibitor

This aromatic a-keto acid and PKU biomarker (FWfree-acid = 164.16 g/mol; CAS 156-06-9 for acid; CAS 114-76-1 for sodium salt; CAS 51828-93-4 for calcium salt); lmax = 320 nm, e = 17500 M–1 cm–1 in 0.7 M NaOH), also known as 2-oxo-3-phenylpropanoic acid and a-oxohydrocinnamic acid, is readily formed by the action of a number of aminotransferases on phenylalanine. Phenylpyruvate is only slightly soluble in boiling water but is soluble in ethanol and diethyl ether. The solid oxidizes in air and decomposes on storage, if not dry. Sodium phenylpyruvate is a watersoluble monohydrate salt. Phenylketonuria: Phenylpyruvate is present at high urinary concentrations in phenylalanine monooxygenase deficiency, better known as Phenylketonuria. Indeed, individuals suffering PKU tend to excrete urine containing large quantities of phenyl-pyruvate, phenyl-acetate and phenyl-lactate, along with phenylalanine. If untreated, mental retardation and microcephaly are evident by the first year, along with irritability, epileptic seizures, and skin lesions. Target(s): acetolactate synthase; aldehyde reductase; apyrase; branched-chain a-keto acid dehydrogenase; [branched-chain a-keto-acid dehydrogenase] kinase, or [3-methyl-2-oxobutanoate dehydrogenase (acetyl-transferring)] kinase; carnitine-acylcarnitine translocase; cathepsin D; choline acetyltransferase; 3-deoxy-7-phosphoheptulonate synthase, or 3-deoxy-D-arabino-heptulosonate 7-phosphate synthetase; dihydropteridine reductase; diphosphomevalonate decarboxylase; glutamate decarboxylase; glutamine:pyruvate aminotransferase; glycerate dehydrogenase, weakly inhibited; hexokinase (human brain), Ki = 2 mM; histidine decarboxylase; 4- hydroxyphenylpyruvate dioxygenase; 3a-hydroxysteroid dihydrogenase; 3b-hydroxysteroid dehydrogenase; hypothalamus acid proteinase; indolepyruvate decarboxylase, Ki = 50 μM; kynureninase; L-lactate dehydrogenase; L-lactate dehydrogenase (cytochrome); mercaptopyruvate sulfurtransferase; mevalonate-5-pyrophosphate decarboxylase; oxaloacetate tautomerase; phenylalanine ammonia-lyase; phenylalanyltRNA synthetase, weakly inhibited, Ki = 7.6 mM; pyruvate carboxylase; pyruvate decarboxylase; pyruvate dehydrogenase; pyruvate kinase (human), Ki = 8.5 mM; pyruvate oxidase; pyruvate transport; stearoyl-CoA 9-desaturase; tryptophan 2- monooxygenase; tryptophan 5-monooxygenase; tyrosinase; and tyrosine 2,3-aminomutase.

Purification Methods

The salt should have no OH broad bands in the IR at ~3000cm-1. If these are present, then they are due either to water contamination or to the presence of free acid. For the first case dry the solid thoroughly in a vacuum over P2O5, and in the latter case wash the salt well with Et2O in vacuo till free of acid. Alternatively add a slight excess of the free acid (cf p 332) in EtOH to ethanolic NaOH, evaporate to dryness and extract excess acid from the salt with dry Et2O. [Beilstein 10 I 325.]

Check Digit Verification of cas no

The CAS Registry Mumber 114-76-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 4 respectively; the second part has 2 digits, 7 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 114-76:
(5*1)+(4*1)+(3*4)+(2*7)+(1*6)=41
41 % 10 = 1
So 114-76-1 is a valid CAS Registry Number.
InChI:InChI=1/C9H8O3.Na.H2O/c10-8(9(11)12)6-7-4-2-1-3-5-7;;/h1-5H,6H2,(H,11,12);;1H2/q;+1;/p-1

114-76-1 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • Price
  • Detail
  • Alfa Aesar

  • (H56767)  Sodium phenylpyruvate, 98%   

  • 114-76-1

  • 5g

  • 393.0CNY

  • Detail
  • Alfa Aesar

  • (H56767)  Sodium phenylpyruvate, 98%   

  • 114-76-1

  • 25g

  • 1224.0CNY

  • Detail
  • Aldrich

  • (P8001)  Sodiumphenylpyruvate  powder

  • 114-76-1

  • P8001-5G

  • 582.66CNY

  • Detail
  • Aldrich

  • (P8001)  Sodiumphenylpyruvate  powder

  • 114-76-1

  • P8001-25G

  • 2,701.53CNY

  • Detail

114-76-1SDS

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 Sodium phenylpyruvate

1.2 Other means of identification

Product number -
Other names Sodium Phenylpyruvate

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:114-76-1 SDS

114-76-1Synthetic route

(Z)-5'-benzylidenecyclohexanespiro-2'-(1',3'-dioxolan)-4'-one
93831-17-5

(Z)-5'-benzylidenecyclohexanespiro-2'-(1',3'-dioxolan)-4'-one

A

cyclohexanone
108-94-1

cyclohexanone

B

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; water for 18h; Ambient temperature;A n/a
B 89%
5-benzylidenehydantoin
3775-01-7, 74805-60-0, 109754-06-5

5-benzylidenehydantoin

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

Conditions
ConditionsYield
With sodium hydroxide In water at 140℃; for 3h; Hydrolysis;77%
L-phenylalanine
63-91-2

L-phenylalanine

sodium pyruvate
113-24-6

sodium pyruvate

A

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

B

rac-Ala-OH
302-72-7

rac-Ala-OH

Conditions
ConditionsYield
With acetate buffer; N(1+)C5His2C16; PL(1+)2C16; copper(II) perchlorate In water at 30℃; for 48h; Kinetics; var. catalysts;A n/a
B 27%
L-phenylalanine
63-91-2

L-phenylalanine

α-ketoglutarate monosodium salt
22202-68-2

α-ketoglutarate monosodium salt

A

Glutamic acid
617-65-2

Glutamic acid

B

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

Conditions
ConditionsYield
With acetate buffer; N(1+)C5His2C16; PL(1+)2C16; copper(II) perchlorate In water at 30℃; for 48h; Kinetics;
(Z)-4-benzylidene-2-methyl-5(4H)-oxazolone
38879-46-8

(Z)-4-benzylidene-2-methyl-5(4H)-oxazolone

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

Conditions
ConditionsYield
With hydrogenchloride; sodium methylate In methanol for 3h; Product distribution; Mechanism;
benzaldehyde
100-52-7

benzaldehyde

HI, I2

HI, I2

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 76 percent / sodium acetate / acetic acid / 5 h / Heating
2: 77 percent / NaOH / H2O / 3 h / 140 °C
View Scheme
5-benzylidenehydantoin
3775-01-7

5-benzylidenehydantoin

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

Conditions
ConditionsYield
With sodium hydroxide In propan-1-ol; water at 125 - 130℃; under 2250.23 Torr; Temperature; Pressure; Inert atmosphere;
cobalt(II) chloride hexahydrate

cobalt(II) chloride hexahydrate

dichloromethane
75-09-2

dichloromethane

tris[(6-methyl-2-pyridyl)methyl]amine
25599-08-0

tris[(6-methyl-2-pyridyl)methyl]amine

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

[{(6Me3TPA)CoII}2(PP)](BPh4)2

[{(6Me3TPA)CoII}2(PP)](BPh4)2

Conditions
ConditionsYield
In methanol at 20℃; for 5h;95%
sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

<15N>-L-phenylalanine
29700-34-3

<15N>-L-phenylalanine

Conditions
ConditionsYield
With formate dehydrogenase; 1,4-dihydronicotinamide adenine dinucleotide; 15N-ammonium formate; phenylalanine dehydrogenase; diothiothreitol Ambient temperature; TRIS, pH=6.5-7.0, 0.1M HCl;92%
sodium tetrachloropalladate(II)

sodium tetrachloropalladate(II)

N-methoxylamine hydrochloride
593-56-6

N-methoxylamine hydrochloride

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

Pd{O2CC(CH2C6H5)N(OCH3)}2
154070-59-4

Pd{O2CC(CH2C6H5)N(OCH3)}2

Conditions
ConditionsYield
With NaOH In water N2; soln. of sodium-α-oxocarboxylate and O-alkylhydroxylamine stirred at room temp. for 10-24 h; soln. of Na2PdCl4 added slowly;; washed with cold water; dried in high vacuum;; recrystd. from EtOH/H2O; elem. anal.;;90%
methanol
67-56-1

methanol

p-hydroxybenzoic acid hydrazone

p-hydroxybenzoic acid hydrazone

dibenzyltin(IV) dichloride
3002-01-5

dibenzyltin(IV) dichloride

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

C31H30N2O5Sn

C31H30N2O5Sn

Conditions
ConditionsYield
at 45 - 65℃; for 15h; Time; Inert atmosphere;89.9%
di(n-butyl)tin oxide
818-08-6

di(n-butyl)tin oxide

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

p-toluic hydrazide
3619-22-5

p-toluic hydrazide

2-carbonyl-3-phenylpropionic acid p-methylbenzoylhydrazone bis-n-butyltin complex

2-carbonyl-3-phenylpropionic acid p-methylbenzoylhydrazone bis-n-butyltin complex

Conditions
ConditionsYield
In methanol at 45 - 65℃; for 24h; Time; Inert atmosphere;88.8%
methanol
67-56-1

methanol

4-methoxybenzoic acid hydrazide
3290-99-1

4-methoxybenzoic acid hydrazide

di(n-butyl)tin oxide
818-08-6

di(n-butyl)tin oxide

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

C52H72N4O10Sn2

C52H72N4O10Sn2

Conditions
ConditionsYield
at 45 - 65℃; for 8h; Inert atmosphere;88.5%
di(n-butyl)tin oxide
818-08-6

di(n-butyl)tin oxide

2-Hydroxybenzoylhydrazine
936-02-7

2-Hydroxybenzoylhydrazine

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

Sn(4+)*C16H12N2O4(2-)*2C4H9(1-)

Sn(4+)*C16H12N2O4(2-)*2C4H9(1-)

Conditions
ConditionsYield
In methanol at 45 - 65℃; for 5h; Inert atmosphere;85.5%
sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

methyl iodide
74-88-4

methyl iodide

sodium 2-oxo-3-phenylbutanoate
125116-72-5

sodium 2-oxo-3-phenylbutanoate

Conditions
ConditionsYield
With sodium hydroxide In methanol; diethyl ether85%
methanol
67-56-1

methanol

diphenyltin(IV) dichloride
1135-99-5

diphenyltin(IV) dichloride

4-hydroxybenzoic acid hydrazide
5351-23-5

4-hydroxybenzoic acid hydrazide

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

C58H52N4O10Sn2

C58H52N4O10Sn2

Conditions
ConditionsYield
at 45 - 65℃; for 5h; Inert atmosphere;84.5%
4-tert-butylbenzoic acid hydrazide
43100-38-5

4-tert-butylbenzoic acid hydrazide

dibenzyltin dichloride
70335-32-9

dibenzyltin dichloride

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

C70H76N4O8Sn2

C70H76N4O8Sn2

Conditions
ConditionsYield
In methanol at 50 - 65℃; for 20h; Concentration; Inert atmosphere;82.8%
sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

Conditions
ConditionsYield
With phosphate buffer; D-glucose; 2-hydroxyethanethiol; sodium chloride; formate dehydrogenase; 1,4-dihydronicotinamide adenine dinucleotide; benzoylformate reductase; bovine serum albumin; yeast alcohol dehydrogenase In ethanol; water; toluene at 30℃; for 48h;80%
With hydrogenchloride; Candida boidinii formate dehydrogenase; ethylenediaminetetraacetic acid; Staphylococcus epidermis D-lactate dehydrogenase; NAD; ammonium formate; 2-hydroxyethanethiol In water for 24h; pH=7; Enzymatic reaction; enantioselective reaction;
potassium 3-phenyl-5-methylhydrido-trispyrazol-1-ylborate

potassium 3-phenyl-5-methylhydrido-trispyrazol-1-ylborate

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

iron(II) chloride

iron(II) chloride

[(hydrotris(3-phenyl-5-methylpyrazolyl)borate)FeII(phenylpyruvate)]

[(hydrotris(3-phenyl-5-methylpyrazolyl)borate)FeII(phenylpyruvate)]

Conditions
ConditionsYield
Stage #1: potassium hydrotris(3-phenyl-5-methyl-pyrazol-1-yl)borate; iron(II) chloride In dichloromethane for 1h;
Stage #2: sodium phenylphyruvate In methanol; dichloromethane for 8h;
80%
sodium tetrachloropalladate(II)

sodium tetrachloropalladate(II)

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

rac-methylbenzylamine
618-36-0

rac-methylbenzylamine

Pd{O2CC(CH2C6H5)N(CH(CH3)C6H5)}2
154070-66-3

Pd{O2CC(CH2C6H5)N(CH(CH3)C6H5)}2

Conditions
ConditionsYield
In methanol N2;α-oxocarboxylate and amine in MeOH stirred at room temp.; Na2PdCl4 added; stirred at room temp. for 1 h;; evapd.; stirred in hexane; crystd.; washed with hexane and water; dried in high vacuo; elem. anal.;;79%
ethanol
64-17-5

ethanol

dibenzyltin(IV) dichloride
3002-01-5

dibenzyltin(IV) dichloride

2-Hydroxybenzoylhydrazine
936-02-7

2-Hydroxybenzoylhydrazine

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

2-carbonyl-3-phenylpropionic acid salicyloyl hydrazone dibenzyltin complex

2-carbonyl-3-phenylpropionic acid salicyloyl hydrazone dibenzyltin complex

Conditions
ConditionsYield
at 45 - 65℃; for 15h; Concentration; Inert atmosphere;78.6%
methanol
67-56-1

methanol

dibenzyltin(IV) dichloride
3002-01-5

dibenzyltin(IV) dichloride

benzoic acid hydrazide
613-94-5

benzoic acid hydrazide

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

C62H60N4O8Sn2

C62H60N4O8Sn2

Conditions
ConditionsYield
at 45 - 65℃; for 15h; Concentration;78.2%
sodium tetraphenyl borate
143-66-8

sodium tetraphenyl borate

tris[(2-pyridylmethyl)amine]
16858-01-8

tris[(2-pyridylmethyl)amine]

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

cobalt(II) perchlorate hexahydrate

cobalt(II) perchlorate hexahydrate

[(TPA)CoII(PPH)](BPh4)
1418284-81-7

[(TPA)CoII(PPH)](BPh4)

Conditions
ConditionsYield
In methanol at 20℃; for 5h;78%
methanol
67-56-1

methanol

di-p-methylbenzyltin(IV) dichloride

di-p-methylbenzyltin(IV) dichloride

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

p-toluic hydrazide
3619-22-5

p-toluic hydrazide

C68H74N4O8Sn2

C68H74N4O8Sn2

Conditions
ConditionsYield
at 50 - 65℃; for 5h; Time;77.9%
methanol
67-56-1

methanol

dibenzyltin(IV) dichloride
3002-01-5

dibenzyltin(IV) dichloride

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

p-toluic hydrazide
3619-22-5

p-toluic hydrazide

C64H64N4O8Sn2

C64H64N4O8Sn2

Conditions
ConditionsYield
at 50 - 65℃; for 20h; Concentration; Inert atmosphere;77.8%
iron(II) perchlorate hexahydrate

iron(II) perchlorate hexahydrate

dichloromethane
75-09-2

dichloromethane

sodium tetraphenyl borate
143-66-8

sodium tetraphenyl borate

tris[(6-methyl-2-pyridyl)methyl]amine
25599-08-0

tris[(6-methyl-2-pyridyl)methyl]amine

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

[(tris(6-methyl-2-pyridylmethyl)amine)2Fe2(phenypyruvate enolato)](BPh4)2 * 0.5(dichloromethane)

[(tris(6-methyl-2-pyridylmethyl)amine)2Fe2(phenypyruvate enolato)](BPh4)2 * 0.5(dichloromethane)

Conditions
ConditionsYield
In methanol ligands and Fe salt in MeOH stirred under Ar for 2 h; pptd. with a MeOH soln. of NaBPh4, filtered, washed (MeOH), dried; elem.anal.;76%
diphenyltin(IV) dichloride
1135-99-5

diphenyltin(IV) dichloride

2-Hydroxybenzoylhydrazine
936-02-7

2-Hydroxybenzoylhydrazine

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

2-oxo-3-phenylpropionic acid salicyloylhydrazone diphenyltin

2-oxo-3-phenylpropionic acid salicyloylhydrazone diphenyltin

Conditions
ConditionsYield
In methanol at 45 - 65℃; for 8h; Concentration;75.8%
N-phenylethylhydroxylamine
3217-93-4

N-phenylethylhydroxylamine

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

N-phenethyl-2-phenylacetamide
5460-60-6

N-phenethyl-2-phenylacetamide

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 15h; Product distribution / selectivity;75%
methanol
67-56-1

methanol

di-p-methylbenzyltin(IV) dichloride

di-p-methylbenzyltin(IV) dichloride

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

N-amino-(4-nitrophenyl)carboxamide
636-97-5

N-amino-(4-nitrophenyl)carboxamide

C66H66N6O12Sn2

C66H66N6O12Sn2

Conditions
ConditionsYield
at 50 - 65℃; for 20h; Inert atmosphere;74.5%
bis(2,4-dichlorobenzyl)tin dichloride
849144-53-2

bis(2,4-dichlorobenzyl)tin dichloride

2-Hydroxybenzoylhydrazine
936-02-7

2-Hydroxybenzoylhydrazine

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

2-oxo-3-phenylpropionic acid salicyloyl hydrazone bis(2,4-dichlorobenzyl)tin

2-oxo-3-phenylpropionic acid salicyloyl hydrazone bis(2,4-dichlorobenzyl)tin

Conditions
ConditionsYield
In ethanol at 45 - 65℃; for 22h; Concentration; Time; Inert atmosphere;74.3%
sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

L-3-phenyllactic acid
20312-36-1

L-3-phenyllactic acid

Conditions
ConditionsYield
With fructose 1,6-bisphosphate trisodium; nicotinamide adenine dinucleotide red. form; piperazine*HCl buffer; sodium formate; diothiothreitol In water lyophilized formate dehydrogenase, mutant lactate dehydrogenase from Bacillus stearothermophilus (BSLDH), pH=6.0;70%
With Fructose 1,6-bisphosphate; piperazine*HCl buffer; sodium formate; nicotinamide adenine dinucleotide; diothiothreitol pH 6.0, lyophilized formate dehydrogenase, lactate dehydrogenase from Bacillus stearothermophilus (BSLDH Q102R/C97G);65%
With fructose 1,6-bisphosphate trisodium; lyophilized formate dehydrogenase; mutant lactate dehydrogenase; nicotinamide adenine dinucleotide red. form; sodium formate; piperazine hydrochloride; diothiothreitol In water at 25℃; Rate constant; other 2-keto acids; other enzymes; stereospecific enzymatic reduction;
di(para-chlorobenzyl)tin(IV) dichloride

di(para-chlorobenzyl)tin(IV) dichloride

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

p-toluic hydrazide
3619-22-5

p-toluic hydrazide

C62H48Cl8N4O6Sn2

C62H48Cl8N4O6Sn2

Conditions
ConditionsYield
In methanol at 45 - 65℃; for 5h; Time; Inert atmosphere;68.5%
sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

methyl iodide
74-88-4

methyl iodide

3-methyl-2-oxo-3-phenylbutanoic acid
91133-59-4

3-methyl-2-oxo-3-phenylbutanoic acid

Conditions
ConditionsYield
With sodium hydroxide In methanol68%
With sodium hydroxide In tetrahydrofuran65%
With sodium hydroxide42%
sodium tetrachloropalladate(II)

sodium tetrachloropalladate(II)

(S)-2-methylbutylamine
34985-37-0

(S)-2-methylbutylamine

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

Pd{O2CC(CH2Ph)N(S-CH2CH(CH3)CH2CH3)}2

Pd{O2CC(CH2Ph)N(S-CH2CH(CH3)CH2CH3)}2

Conditions
ConditionsYield
In methanol N2;α-oxocarboxylate and amine in MeOH stirred at room temp.; Na2PdCl4 added; stirred at room temp. for 1 h;; evapd.; stirred in hexane; crystd.; washed with hexane and water; dried in high vacuo; elem. anal.;;68%
sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

6,7-diamino-8-chloroquinoline
261764-97-0

6,7-diamino-8-chloroquinoline

3-benzyl-5-chloropyrido[2,3-g]quinoxalin-2(1H)-one
1037303-28-8

3-benzyl-5-chloropyrido[2,3-g]quinoxalin-2(1H)-one

Conditions
ConditionsYield
Stage #1: sodium phenylphyruvate; 6,7-diamino-8-chloroquinoline With sulfuric acid In water at 60℃; for 1h;
Stage #2: With sodium hydroxide In water
66%
With sulfuric acid In water; N,N-dimethyl-formamide at 60℃; for 1h;

114-76-1Relevant articles and documents

Mechanism of the Hydrolysis of (Z)-4-Benzylidene-2-methyloxazolin-5-one or (Z)-4-Benzylidene-2-phenyloxazolin-5-one Derivatives

Suh, Junghun,Lee, Eun,Myoung, Young Chan,Kim, Minwoo,Kim, Soodan

, p. 977 - 980 (1985)

The methyl (1a) and the phenyl (2) derivatives of (Z)-4-benzylideneoxazolin-5-one were hydrolyzed at comparable rates under alkaline conditions.In contrast, the acidic hydrolysis of 2 was at least 10E5 times slower than that of 1a.The Hammett ρ value obtained from the acidic hydrolysis of the phenyl substituted derivatives of 1a was 0.20 +/- 0.09 while that from the corresponding basic hydrolysis was 1.50 +/- 0.11.Methanolysis of 1a under basic conditions produced the methyl ester of (Z)-α-(acetylamino)cinnamic acid, and that under acidic conditions led to products consistent with the attack of methanol at the imine carbon.These results indicate that the alkaline hydrolysis of the oxazolin-5-one derivatives occurs through nucleophilic attack at the carbonyl carbon of the substrate and the acidic hydrolysis through that at the imine carbon.

Synthesis of isotopically labelled L-phenylalanine and L-tyrosine

Raap, Jan,Nieuwenhuis, Saskia,Creemers, Alain,Hexspoor, Sander,Kragl, Udo,Lugtenburg, Johan

, p. 2609 - 2621 (2007/10/03)

A synthetic route to stable-isotope-substituted L-phenylalanine is presented, which allows the introduction of 13C, 15N, and deuterium labels at any position or combination of positions. For labelling of the aromatic ring, a synthetic route to ethyl benzoate (or benzonitrile) has been developed, based on the electrocyclic ring-closure of a 1,6-disubstituted hexatriene system, with in situ aromatization by elimination of one (amino) substituent. Several important (highly isotopically enriched) synthons have been prepared, namely benzonitrile, benzaldehyde, ethyl benzoate, and ethyl diphenyloxyacetate. Labelled L-phenylalanines have been synthesized from both aromatic precursors by initial conversion into sodium phenylpyruvate and subsequent transformation of this intermediate into the L-α-amino acid by an enzymatic reductive amination reaction. In this manner, highly enriched phenylalanines are obtained on the 10-gram scale and with high enantiomeric purities (≥ 99% ee). The method has been validated by the synthesis of [1'13C]-L-Phe and [2-D]-L-Phe. In addition, two methods are described for the introduction of isotopes into L-tyrosine starting from the isotopically enriched precursors benzonitrile and ethyl benzoate.

Dioxolanones as Synthetic Intermediates. Part 1. Synthesis of α-Keto Acids, α-Keto Aldehydes, and α-Ketols

Ramage, Robert,Griffiths, Gareth J.,Shutt, Fiona E.,Sweeney, John N. A.

, p. 1531 - 1537 (2007/10/02)

2,2-Pentamethylene-1,3-dioxolan-4-one (10) has been elaborated to provide 5'-ylidene derivatives using a Wittig approach.This apparently novel class of compounds is subject to nucleophilic attack at the 4-position because of strain inherent in the 5-membered ring.Thus alkaline hydrolysis leads to the formation of α-keto acids; hydride reduction of dioxolanones incorporating conjugated aryl substituents using di-isobutylaluminium hydride leads to α-keto-aldehydes; the reaction of dioxolanone (15) with methylmagnesium iodide gave the α-ketol (40).

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