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2-Cyclopenten-1-one

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CAS:930-30-3
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CAS:930-30-3
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  • CAS:930-30-3
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  • CAS:930-30-3
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  • Purity: 98%
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  • CAS:930-30-3
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2-Cyclopenten-1-one Basic information
Product Name:2-Cyclopenten-1-one
Synonyms:2-CYCLOPENTEN-1-ONE;2-CYCLOPENTENE-1-ONE;2-CYCLOPENTENONE;CPEO;CYCLOPENT-2-ENONE;2_cyclopenten-1-0ne;2-cyclopenten-1-0ne;2-Cyclopentenone-1
CAS:930-30-3
MF:C5H6O
MW:82.1
EINECS:213-213-0
Product Categories:Ring Systems;C3 to C6;Carbonyl Compounds;Ketones;Pyridines
Mol File:930-30-3.mol
2-Cyclopenten-1-one Structure
2-Cyclopenten-1-one Chemical Properties
Boiling point 64-65 °C19 mm Hg(lit.)
density 0.98 g/mL at 25 °C(lit.)
refractive index n20/D 1.481(lit.)
Fp 108 °F
storage temp. 2-8°C
solubility soluble in Chloroform, Methanol
form Liquid
color Clear yellow
Specific Gravity0.980
Water Solubility almost insoluble
BRN 1446054
InChIInChI=1S/C5H6O/c6-5-3-1-2-4-5/h1,3H,2,4H2
InChIKeyBZKFMUIJRXWWQK-UHFFFAOYSA-N
SMILESC1(=O)CCC=C1
LogP-0.114 (est)
CAS DataBase Reference930-30-3(CAS DataBase Reference)
NIST Chemistry Reference2-Cyclopenten-1-one(930-30-3)
Safety Information
Hazard Codes Xi,Xn
Risk Statements 10-37-36/37/38-22
Safety Statements 16-36-36/37/39
RIDADR UN 1224 3/PG 3
WGK Germany 3
8
Hazard Note Irritant
HazardClass 3
PackingGroup III
HS Code 29142990
MSDS Information
ProviderLanguage
2-Cyclopenten-1-one English
SigmaAldrich English
ACROS English
ALFA English
2-Cyclopenten-1-one Usage And Synthesis
Description2-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].
Chemical Propertiesclear yellow liquid
Uses2-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.
DefinitionChEBI: 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.
Preparation2-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.
Synthesis of 2-Cyclopenten-1-one
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
References[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.
Tag:2-Cyclopenten-1-one(930-30-3) Related Product Information
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