Ethyl 3-oxo-4-phenylbutanoate Struktur

Ethyl 3-oxo-4-phenylbutanoate

Bezeichnung:Ethyl 3-oxo-4-phenylbutanoate

CAS-Nr718-08-1

Englisch Name:Ethyl 3-oxo-4-phenylbutanoate

CBNumberCB6199162

SummenformelC12H14O3

Molgewicht206.24

MOL-Datei718-08-1.mol

Ethyl 3-oxo-4-phenylbutanoate physikalisch-chemischer Eigenschaften

Siedepunkt	290℃
Dichte	1.091
Brechungsindex	1.054-1.059
Flammpunkt	124℃
storage temp.	Inert atmosphere,Room Temperature
Löslichkeit	Chloroform (Slightly), DMSO (Slightly), Methanol (Sparingly)
Aggregatzustand	Oil
pka	10.49±0.46(Predicted)
Farbe	Colourless to Light Yellow
InChI	InChI=1S/C12H14O3/c1-2-15-12(14)9-11(13)8-10-6-4-3-5-7-10/h3-7H,2,8-9H2,1H3
InChIKey	BOZNWXQZCYZCSH-UHFFFAOYSA-N
SMILES	C1(C=CC=CC=1)CC(=O)CC(=O)OCC

Sicherheit

R-Sätze:	36/37/38
S-Sätze:	26-36/37/39

Gefahreninformationscode (GHS)

Ethyl 3-oxo-4-phenylbutanoate Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
Chemische Eigenschaften
Light-yellow Liquid.
Verwenden
Ethyl 3-oxo-4-phenylbutanoate is a useful synthetic intermediate. It is used to prepare pyrazolone derivatives as antiprion compounds. It is also used to prepare pyrrolinylaminopyrimidine analogs as inhibitors of AP-1 and NF-κB mediated gene expression.
Synthesis Reference(s)
Journal of Medicinal Chemistry, 44, p. 78, 2001 DOI: 10.1021/jm001034k
Chemical and Pharmaceutical Bulletin, 30, p. 2440, 1982 DOI: 10.1248/cpb.30.2440
Synthese
The synthesis of Ethyl 3-oxo-4-phenylbutanoate is as follows:Monoethyl monopotassium malonate (12.9 g, 2.3 equivalents) was mixed with tetrahydrofuran (200 ml), and the mixture was cooled to 5°C. Triethylamine (8.2 g, 2.5 equivalents) and magnesium chloride (8.62 g, 2.8 equivalents) were added, and the mixture was stirred at 5 to 20°C for 3 hours. The reaction mixture was cooled to 5°C. Phenacyl chloride (5 g, 32 mmol, 1 equivalent) was gradually added, and the mixture was stirred at 5 to 20°C for 63 hours. The mixture was cooled to 5°C, and 1 N hydrochloric acid (30 ml) was added. Tetrahydrofuran was evaporated away under reduced pressure, and extraction was carried out with ethyl acetate (50 ml). The organic layer was washed with 1 N hydrochloric acid (30 ml), water (10 ml), saturated aqueous solution of sodium hydrogencarbonate (30 ml) and water (10 ml) in order. The solvent was evaporated away under reduced pressure to obtain the Ethyl 3-oxo-4-phenylbutanoate as a pale yellow oil (5.82 g, yield: 86 %).

Ethyl 3-oxo-4-phenylbutanoate Upstream-Materialien And Downstream Produkte

Ethyl 3-oxo-4-phenylbutanoate Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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