2,3,4,5-TETRAMETHYL-2-CYCLOPENTENONE Struktur

2,3,4,5-TETRAMETHYL-2-CYCLOPENTENONE

Bezeichnung:2,3,4,5-TETRAMETHYL-2-CYCLOPENTENONE

CAS-Nr54458-61-6

Englisch Name:2,3,4,5-TETRAMETHYL-2-CYCLOPENTENONE

CBNumberCB9325814

SummenformelC9H14O

Molgewicht138.21

MOL-Datei54458-61-6.mol

2,3,4,5-TETRAMETHYL-2-CYCLOPENTENONE physikalisch-chemischer Eigenschaften

Siedepunkt	100 °C30 mm Hg(lit.)
Dichte	0.927 g/mL at 20 °C(lit.)
Brechungsindex	n20/D 1.476
Flammpunkt	164 °F
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
Löslichkeit	Chloroform, Methanol
Aggregatzustand	Oil
Farbe	Clear Colourless
Wichte	0.917
Wasserlöslichkeit	Not miscible with water.
BRN	2324088
InChI	InChI=1S/C9H14O/c1-5-6(2)8(4)9(10)7(5)3/h5,7H,1-4H3
InChIKey	ARUAYSANQMCCEN-UHFFFAOYSA-N
SMILES	C1(=O)C(C)C(C)C(C)=C1C
CAS Datenbank	54458-61-6(CAS DataBase Reference)

Sicherheit

S-Sätze:	23-24/25-35-3/9/49-43-36-15
WGK Germany	3
HS Code	29142990

Gefahreninformationscode (GHS)

2,3,4,5-TETRAMETHYL-2-CYCLOPENTENONE Chemische Eigenschaften,Einsatz,Produktion Methoden

S-Sätze Betriebsanweisung:
S23:Gas/Rauch/Dampf/Aerosol nicht einatmen(geeignete Bezeichnung(en) vom Hersteller anzugeben).
S24/25:Berührung mit den Augen und der Haut vermeiden.
Verwenden
2,3,4,5-Tetramethyl-2-cyclopentenone was used in the synthesis of chiral pre-ligands, (R)-3,3?-bis(tetramethylcyclopentadienyl)-2,2?-bismethoxy-1,1?-bisnaphthalene and (R)-3-tetramethylcyclopentadienyl-2,2?-bismethoxy-1,1?-bisnaphthalene by reacting with (R)-3,3?-dilithium-2,2?-bismethoxy-1,1?-bisnaphthalene.
Verwenden
2,3,4,5-Tetramethyl-2-cyclopentenone can be used as organic synthesis intermediates and pharmaceutical intermediates, mainly used in laboratory research and development processes and chemical production processes.
Synthese

In a bottom round flask equipped with a mechanical stirrer, a dropping funnel and a reflux condenser was loaded 2000g (23.2 mol) of the starting ketone with 75% w/w of butylacetate as the solvent, 0.35 molar equivalents of anhydrous magnesium chloride and the aforementioned titanium catalytic solution containing 0.06 molar equivalents of the trichloropropoxytitanium complex. The resulting suspension was stirred vigorously and allowed to heat to 90°C. Then 2 molar equivalents of the acetaldehyde were added dropwise over 3h at 90°C. The reaction was continued for an additional hour and cooled to 40°C. The reaction mixture was hydrolysed with a 10% aqueous acetic acid solution and neutralised with a 20% aqueous potassium carbonate solution. The resulting organic phase was directly fractionated into a laboratory Sulzer packed column, to afford the title compound, as a mixture of isomers trans:cis = 85:15, in 27 % yield and the enone (II) (i.e. 4-methyl-4-hexen-3-one) in 31 % yield. mixture of isomers trans:cis = (B.p. = 70-80°C at P = 8 mbar); 4-methyl-4-hexen-3-one = (B.p. = 45-65°C at P = 8 mbar). 1H-NMR (isomer trans): 1.15 (d 3H); 1.19 (d 3H); 1.68 (s 3H); 1.88 (m 1H); 1.98 (s 3H); 2.25 (m 1H). 13C-NMR (isomer trans): 8.5; 14.6; 15.1 ; 17.7; 46.2; 48.4; 134.5; 171.6; 21 1.0.

2,3,4,5-TETRAMETHYL-2-CYCLOPENTENONE Upstream-Materialien And Downstream Produkte

2,3,4,5-TETRAMETHYL-2-CYCLOPENTENONE Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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