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Details

Stereochemistry ACHIRAL
Molecular Formula C5H6O
Molecular Weight 82.1005
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 2-CYCLOPENTENONE

SMILES

O=C1CCC=C1

InChI

InChIKey=BZKFMUIJRXWWQK-UHFFFAOYSA-N
InChI=1S/C5H6O/c6-5-3-1-2-4-5/h1,3H,2,4H2

HIDE SMILES / InChI

Molecular Formula C5H6O
Molecular Weight 82.1005
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

PubMed

PubMed

TitleDatePubMed
Stereochemical and skeletal diversity arising from amino propargylic alcohols.
2010-06-18
Chemical and biochemical study of industrially produced San Simón da Costa smoked semi-hard cow's milk cheeses: Effects of storage under vacuum and different modified atmospheres.
2010-05
Highly endo-selective and enantioselective 1,3-dipolar cycloaddition of azomethine ylide with alpha-enones catalyzed by a silver(I)/ThioClickFerrophos complex.
2010-04-16
Marine pyrrolocarbazoles and analogues: synthesis and kinase inhibition.
2009-12-01
Effects of 15-deoxy-delta 12, 14-prostaglandin J2 on the expression of p53 in MCF-7 cells.
2009-08
Identification of advanced reaction products originating from the initial 4-oxo-2-nonenal-cysteine Michael adducts.
2009-05
Use of MEKC for the analysis of reactant and product of Baylis-Hillman reaction.
2009-05
Intermolecular antiselective and enantioselective reductive coupling of enones and aromatic aldehydes with chiral Rh(Phebox) catalysts.
2009-02-19
Synthesis and evaluation of guanidinyl pyrrolidines as bifunctional catalysts for enantioselective conjugate additions to cyclic enones.
2009-01-21
Gold-catalyzed hydrative carbocyclization of 1,5- and 1,6-diyn-3-ones via an oxygen transfer process.
2008-11-07
A rapid microwell fluorescence immunoassay for cellular protein detection.
2008-09-22
Matrix isolation studies of photochemical and thermal reactions of 3- and 5-membered cyclic hydrocarbons with CrCl2O2.
2008-06-19
Pro-apoptotic activity of cyclopentenone in cancer cells.
2008-04-04
Asymmetric Morita-Baylis-Hillman reaction of arylaldehydes with 2-cyclohexen-1-one catalyzed by chiral bis(thio)urea and DABCO.
2008-03-20
A general and regioselective synthesis of cyclopentenone derivatives through nickel(0)-mediated [3 + 2] cyclization of alkenyl Fischer carbene complexes and internal alkynes.
2007-11-21
N-heterocyclic carbene catalyzed aza-Morita-Baylis-Hillman reaction of cyclic enones with N-tosylarylimines.
2007-09-14
Jet-cooled phosphorescence excitation spectrum of the T1(n,pi*) <-- S0 transition of 2-cyclopenten-1-one.
2007-08-30
Metal-catalyzed chemoselective cycloisomerization of cis-2,4-dien-1-als to 3-cyclopentenones and 4-alkylidene-3,4-dihydro-2H-pyrans.
2006-07-06
The cyclopentenone 15-deoxy-delta(12,14)-prostaglandin J2 inhibits G1/S transition and retinoblastoma protein phosphorylation in immortalized lymphocytes from Alzheimer's disease patients.
2005-10
New silicon-mediated, sequential ring expansions of n-sized 2-cycloalkenones into hydroxyolefinic n + m + p medium-sized lactones: short synthesis of (-)-phoracantholide-J.
2005-09-15
Phenols, quinolines, indoles, benzene, and 2-cyclopenten-1-ones are oviductal toxicants in cigarette smoke.
2005-07
Stereoselective Nazarov cyclizations of bridged bicyclic dienones.
2005-06-23
3,3a-Dihydrocyclopenta[b]chromen-1(2H)-ones from the reaction of salicylaldehyde and 2-cyclopenten-1-one.
2005-05
Effects of cyclopentenone prostaglandins on the expression of heme oxygenase-1 in MCF-7 cells.
2004-12
Protein thiol modification by 15-deoxy-Delta12,14-prostaglandin J2 addition in mesangial cells: role in the inhibition of pro-inflammatory genes.
2004-11
Theoretical study of the vinyl allene oxide to cyclopent-2-en-1-one rearrangement: mechanism, torquoselectivity and solvent effects.
2004-05-28
15d-PGJ2 inhibits oxidized LDL-induced macrophage proliferation by inhibition of GM-CSF production via inactivation of NF-kappaB.
2004-02-13
Straightforward asymmetric entry to highly functionalized 3-substituted 3-hydroxy-beta-lactams via Baylis-Hillman or bromoallylation reactions.
2004-02-06
New Fischer carbene complexes of rhodium(i): preparation and 2-cyclopentenone ring synthesis by annelation to alkynes.
2004-01-21
Practical synthesis of D- and l-2-cyclopentenone and their utility for the synthesis of carbocyclic antiviral nucleosides against orthopox viruses (smallpox, monkeypox, and cowpox virus).
2003-11-14
Urease inhibitory activity of simple alpha,beta-unsaturated ketones.
2003-10-24
Practical synthesis of D-cyclopent-2-enone, the key intermediate of carbocyclic nucleosides.
2003-10-21
2-Cyclopenten-1-one and prostaglandin J2 reduce restenosis after balloon angioplasty in rats: role of NF-kappaB.
2003-10-09
The stereochemistry of the thermal cheletropic decarbonylation of 3-cyclopentenone as determined by multiphoton infrared photolysis/thermolysis.
2003-07-16
Anti-inflammatory activity of 15-deoxy-delta12,14-PGJ2 and 2-cyclopenten-1-one: role of the heat shock response.
2003-07
Antiviral activity of cyclopentenyl nucleosides against orthopox viruses (Smallpox, monkeypox and cowpox).
2003-01-06
Acyl-lithiation of olefins: formation of cyclopentenones from 1-lithio-butadienes and CO.
2002-12-26
Photodimerisation of enones in a clay microenvironment.
2002-12
Hemilabile amidomonophosphine ligand-rhodium(I) complex-catalyzed asymmetric 1,4-addition of arylboronic acids to cycloalkenones.
2002-07-31
Systematic studies on structure and physiological activity of cyclic alpha-keto enamines, a novel class of "cooling" compounds.
2001-11
Highly regio- and stereoselective 1,1-cycloaddition of carbon monoxide with 1,4-dilithio-1,3-dienes. Novel synthetic methods for 3-cyclopenten-1-one derivatives.
2001-10-24
Synthesis of a muscarinic receptor antagonist via a diastereoselective Michael reaction, selective deoxyfluorination and aromatic metal-halogen exchange reaction.
2001-10-05
Lewis base effects in the Baylis-Hillman reaction of imines with cyclohex-2-en-1-one and cyclopent-2-en-1-one.
2001-09-21
Discovery of a new efficient chiral ligand for copper-catalyzed enantioselective Michael additions by high-throughput screening of a parallel library.
2001-06-18
Change of the reaction pattern by methodological variations in a multicomponent assembly promoted by Ni complexes.
2001-04-01
Differential effects of 15-deoxy-delta(12,14)-prostaglandin J2 and a peroxisome proliferator-activated receptor gamma agonist on macrophage activation.
2001-04
Patents
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:20:36 GMT 2025
Edited
by admin
on Mon Mar 31 19:20:36 GMT 2025
Record UNII
Q0U2IGF9CK
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NSC-73117
Preferred Name English
2-CYCLOPENTENONE
Systematic Name English
2-CYCLOPENTEN-1-ONE
Systematic Name English
CYCLOPENT-2-EN-1-ONE
Systematic Name English
CYCLOPENTEN-3-ONE
Systematic Name English
1-CYCLOPENTEN-3-ONE
Systematic Name English
1-CYCLOPENTEN-5-ONE
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID60870802
Created by admin on Mon Mar 31 19:20:36 GMT 2025 , Edited by admin on Mon Mar 31 19:20:36 GMT 2025
PRIMARY
CAS
930-30-3
Created by admin on Mon Mar 31 19:20:36 GMT 2025 , Edited by admin on Mon Mar 31 19:20:36 GMT 2025
PRIMARY
NSC
73117
Created by admin on Mon Mar 31 19:20:36 GMT 2025 , Edited by admin on Mon Mar 31 19:20:36 GMT 2025
PRIMARY
WIKIPEDIA
Cyclopentenone
Created by admin on Mon Mar 31 19:20:36 GMT 2025 , Edited by admin on Mon Mar 31 19:20:36 GMT 2025
PRIMARY
FDA UNII
Q0U2IGF9CK
Created by admin on Mon Mar 31 19:20:36 GMT 2025 , Edited by admin on Mon Mar 31 19:20:36 GMT 2025
PRIMARY
ECHA (EC/EINECS)
213-213-0
Created by admin on Mon Mar 31 19:20:36 GMT 2025 , Edited by admin on Mon Mar 31 19:20:36 GMT 2025
PRIMARY
CHEBI
141550
Created by admin on Mon Mar 31 19:20:36 GMT 2025 , Edited by admin on Mon Mar 31 19:20:36 GMT 2025
PRIMARY
PUBCHEM
13588
Created by admin on Mon Mar 31 19:20:36 GMT 2025 , Edited by admin on Mon Mar 31 19:20:36 GMT 2025
PRIMARY