2-CYCLOHEXENONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H8O
Molecular Weight	96.1271
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O=C1CCCC=C1

InChI

InChIKey=FWFSEYBSWVRWGL-UHFFFAOYSA-N

InChI=1S/C6H8O/c7-6-4-2-1-3-5-6/h2,4H,1,3,5H2

HIDE SMILES / InChI

Molecular Formula	C6H8O
Molecular Weight	96.1271
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

PubMed

Title	Date	PubMed
Novel gamma-secretase inhibitors discovered by library screening of in-house synthetic natural product intermediates.	2006-07-15	16682195
Nucleophilic addition to (3-methylpentadienyl)iron(1+) cations: counterion control of regioselectivity; application to the enantioselective synthesis of 4,5-disubstituted cyclohexenones.	2006-05-10	16669637
A superior P-H phosphonite: asymmetric allylic substitutions with fenchol-based palladium catalysts.	2006-03-30	16573833
Synthesis of (+)-sch 642305 by a biomimetic transannular Michael reaction.	2006-03-30	16562872
High stereoselectivity on low temperature Diels-Alder reactions.	2005-12-09	16542029
2-Amino-4-(2-methoxyphenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile and 2-amino-4-(2-methoxyphenyl)-7,7-dimethyl-3-nitro-4,6,7,8-tetrahydro-5H-chromen-5-one hemihydrate.	2005-12	16330864
Facile preparation of a new BINAP-based building block, 5,5'-diiodoBINAP, and its synthetic application.	2005-11-25	16292868
Tetrahydropyran rings from a Mukaiyama-Michael cascade reaction.	2005-11-23	16287289
Probing the "additive effect" in the proline and proline hydroxamic acid catalyzed asymmetric addition of nitroalkanes to cyclic enones.	2005-11	16189834
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	16146412
Chiral binaphthyl-derived amine-thiourea organocatalyst-promoted asymmetric Morita-Baylis-Hillman reaction.	2005-09-15	16146410
Proton transfer in the oxidative half-reaction of pentaerythritol tetranitrate reductase. Structure of the reduced enzyme-progesterone complex and the roles of residues Tyr186, His181, His184.	2005-09	16156787
An exceptional P-H phosphonite: biphenyl-2,2'-bisfenchylchlorophosphite and derived ligands (BIFOPs) in enantioselective copper-catalyzed 1,4-additions.	2005-08-26	16542019
Sequential aminodiene Diels-Alder approach to the ergoline skeleton.	2005-08-19	16095303
Role of active site residues and solvent in proton transfer and the modulation of flavin reduction potential in bacterial morphinone reductase.	2005-07-22	15905167
Tandem Sakurai-aldol addition reactions as a route to structurally complex carbocycles.	2005-05-27	15903314
Preparation of 2- and 4-arylmethyl N-substituted and N,N-disubstituted anilines via a "green", multicomponent reaction.	2005-04-14	15816743
Reaction of morphinone reductase with 2-cyclohexen-1-one and 1-nitrocyclohexene: proton donation, ligand binding, and the role of residues Histidine 186 and Asparagine 189.	2005-03-18	15632179
C-H...O hydrogen bonds in cyclohexenone reveal the spectroscopic behavior of Csp3-H and Csp2-H donors.	2005-03	15799475
Opening the 'black box': oscillations in organocuprate conjugate addition reactions.	2005-02-21	15700059
Synthesis of an analogue of the marine polypropionate tridachiahydropyrone.	2005-02-03	15673251
Three oxygenated cyclohexenone derivatives produced by an endophytic fungus.	2005-02	15725652
Parallel mechanistic studies on the counterion effect of manganese salen and porphyrin complexes on olefin epoxidation by iodosylarenes.	2005-02	15621274
Structural assignment of Diels-Alder adducts: an experimental and theoretical approach.	2005-01-01	15556436
On the role of PIII ligands in the conjugate addition of diorganozinc derivatives to enones.	2004-11-19	15515102
Highly enantioselective conjugate additions of potassium organotrifluoroborates to enones by use of monodentate phosphoramidite ligands.	2004-11-12	15527289
Synthesis and antinematodal activity of 3-n-alkylphenols.	2004-11	15564683
Protein thiol modification by 15-deoxy-Delta12,14-prostaglandin J2 addition in mesangial cells: role in the inhibition of pro-inflammatory genes.	2004-11	15317873
Oxygen-promoted palladium(II) catalysis: facile C(sp2)-C(sp2) bond formation via cross-coupling of alkenylboronic compounds and olefins.	2004-10-28	15496093
A short route to enantiomerically pure benzophenanthridinone skeleton: synthesis of lactone analogues of narciclasine and lycoricidine.	2004-10-01	15387596
Catalytic enantioselective conjugate addition of trimethylsilylacetylene to 2-cyclohexen-1-one.	2004-09-16	15355058
Brønsted acid-promoted cyclizations of siloxyalkynes with arenes and alkenes.	2004-08-25	15315407
Highly enantioselective Cu-catalysed asymmetric 1,4-addition of diphenylzinc to cyclohexenone.	2004-08-21	15306908
2-Amino-4-(1-naphthyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile and 2-amino-7,7-dimethyl-4-(1-naphthyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile.	2004-05	15131384
NaOH-catalyzed thiolysis of alpha,beta-epoxyketones in water. A key step in the synthesis of target molecules starting from alpha,beta-unsaturated ketones.	2004-04-02	15049624
Two compounds from allelopathic rice accession and their inhibitory activity on weeds and fungal pathogens.	2004-04	15110693
Different reaction modes for the oxidative dimerization of epoxyquinols and epoxyquinones. Importance of intermolecular hydrogen-bonding.	2004-03-05	14987010
Novel enhancement of diastereoselectivity of [2 + 2] photocycloaddition of chiral cyclohexenones to ethylene by adding naphthalenes.	2004-02-06	14750805
An aza-steroidal [17,16-c]pyrazole derivative: 2'-(p-fluorophenyl)-17a-aza-2'H-pyrazolo[4',3':16,17]-D-homoandrost-4-en-3-one.	2004-02	14767145
Structure and expression of 12-oxophytodienoate reductase (subgroup I) genes in pea, and characterization of the oxidoreductase activities of their recombinant products.	2004-02	14727182
Catalytic asymmetric Michael reaction of beta-keto esters: effects of the linker heteroatom in linked-BINOL.	2003-12-24	14677975
H-tunneling in the multiple H-transfers of the catalytic cycle of morphinone reductase and in the reductive half-reaction of the homologous pentaerythritol tetranitrate reductase.	2003-11-07	12941965
Urease inhibitory activity of simple alpha,beta-unsaturated ketones.	2003-10-24	14519447
2-azabicyclo[2.2.2]octa-3,5-dione via a nitrile Diels-Alder reaction.	2003-10-17	14535813
Asymmetric Morita-Baylis-Hillman reactions catalyzed by chiral Brønsted acids.	2003-10-08	14518986
Synthesis of (-)-tetrodotoxin: preparation of an advanced cyclohexenone intermediate.	2003-10-03	14510553
Particle growth by acid-catalyzed heterogeneous reactions of organic carbonyls on preexisting aerosols.	2003-09-01	12967102
Alpha,beta-unsaturated carbonyl compounds: induction of oxidative DNA damage in mammalian cells.	2003-09	12960416
Investigation of the asymmetric ionic Diels-Alder reaction for the synthesis of cis-decalins.	2003-08-21	12968338
High-pressure selectivity studies--a simple route to a homochiral wistarin precursor.	2003-08-18	12916109

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:46:13 GMT 2025` Edited by `admin` on `Mon Mar 31 18:46:13 GMT 2025`
Record UNII	445160R1U6
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

2-CYCLOHEXENONE

Systematic Name

English

FEMA NO. 4517

Preferred Name

English

NSC-59710

Code

English

CYCLOHEXEN-3-ONE

Systematic Name

English

3-OXOCYCLOHEXENE

Systematic Name

English

2-CYCLOHEXEN-1-ONE

Systematic Name

English

CYCLOHEXENE-1-ONE, 2-

Systematic Name

English

Classification Tree Code System Code

JECFA EVALUATION

2-CYCLOHEXENONE