Cyclopenten-2-on

Bezeichnung:Cyclopenten-2-on

CAS-Nr930-30-3

Englisch Name:2-Cyclopenten-1-one

CBNumberCB3744099

SummenformelC5H6O

Molgewicht82.1

MOL-Datei930-30-3.mol

Synonyma

Cyclopenten-2-on

Cyclopenten-2-on physikalisch-chemischer Eigenschaften

Siedepunkt	64-65 °C19 mm Hg(lit.)
Dichte	0.98 g/mL at 25 °C(lit.)
Brechungsindex	n20/D 1.481(lit.)
Flammpunkt	108 °F
storage temp.	2-8°C
Löslichkeit	soluble in Chloroform, Methanol
Aggregatzustand	Liquid
Wichte	0.980
Farbe	Clear yellow
Wasserlöslichkeit	almost insoluble
BRN	1446054
InChI	InChI=1S/C5H6O/c6-5-3-1-2-4-5/h1,3H,2,4H2
InChIKey	BZKFMUIJRXWWQK-UHFFFAOYSA-N
SMILES	C1(=O)CCC=C1
LogP	-0.114 (est)
CAS Datenbank	930-30-3(CAS DataBase Reference)
NIST chemische Informationen	2-Cyclopenten-1-one(930-30-3)

Sicherheit

Kennzeichnung gefährlicher	Xi,Xn
R-Sätze:	10-37-36/37/38-22
S-Sätze:	16-36-36/37/39
RIDADR	UN 1224 3/PG 3
WGK Germany	3
F	8
Hazard Note	Irritant
HazardClass	3
PackingGroup	III
HS Code	29142990
Speicherklasse	3 - Flammable liquids
Hazard Classifications	Flam. Liq. 3

Gefahreninformationscode (GHS)

2-Cyclopenten-1-one Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R10:Entzündlich.
R37:Reizt die Atmungsorgane.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R22:Gesundheitsschädlich beim Verschlucken.
S-Sätze Betriebsanweisung:
S16:Von Zündquellen fernhalten - Nicht rauchen.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
Beschreibung
2-Cyclopentenone contains two functional groups, a ketone and an alkene. It is a colourless liquid. 2-cyclopenten-1-one selectively induces the expression of the 70-kDa HSP (HSP70) in human cells through cycloheximide-sensitive activation of heat shock transcription factor 1 (HSF1). It is a natural product found in Perilla frutescens[1].
Chemische Eigenschaften
clear yellow liquid
Verwenden
2-Cyclopenten-1-one is a versatile electrophile employed in various addition reactions including conjugate addition of organocopper nucleophiles, Michael reaction with silyl enol ethers and siloxanes. It is also used in Diels-Alder cycloadditions and phosphoniosilylations.
Definition
ChEBI: 2-cyclopenten-1-one is an enone that is cyclopentanone having a C=C double bond at position 2. It has a role as a Hsp70 inducer. It is an enone and an alicyclic ketone.
synthetische
2-Cyclopentenones can be synthesized in a number of ways. One of the routes involves elimination of α-bromo-cyclopentanone using lithium carbonate and Claisen condensation-decarboxylation-isomerization cascades of unsaturated diesters as shown below.

The acid-catalyzed dehydration of cyclopentanediols affords cyclopentenone.
As a functional group, the synthesis of 2-cyclopentenones is accomplished in a variety of other ways, including the Nazarov cyclization reaction from divinyl ketones, Saegusa–Ito oxidation from cyclopentanones, ring-closing metathesis from the corresponding dienes, oxidation of the corresponding cyclic allylic alcohols, and the Pauson–Khand reaction from alkenes, alkynes, and carbon monoxide.
en.wikipedia.org
Einzelnachweise
[1] A Rossi, M G Santoro, G Elia. “2-Cyclopenten-1-one, a new inducer of heat shock protein 70 with antiviral activity.” The Journal of Biological Chemistry 271 50 (1996): 32192–6.

2-Cyclopenten-1-one Upstream-Materialien And Downstream Produkte

Cyclopenten-2-on Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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