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
High-pressure selectivity studies--a simple route to a homochiral wistarin precursor.	2003 Aug 18	12916109
Investigation of the asymmetric ionic Diels-Alder reaction for the synthesis of cis-decalins.	2003 Aug 21	12968338
Catalytic asymmetric Michael reaction of beta-keto esters: effects of the linker heteroatom in linked-BINOL.	2003 Dec 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 Nov 7	12941965
2-azabicyclo[2.2.2]octa-3,5-dione via a nitrile Diels-Alder reaction.	2003 Oct 17	14535813
Urease inhibitory activity of simple alpha,beta-unsaturated ketones.	2003 Oct 24	14519447
Synthesis of (-)-tetrodotoxin: preparation of an advanced cyclohexenone intermediate.	2003 Oct 3	14510553
Asymmetric Morita-Baylis-Hillman reactions catalyzed by chiral Brønsted acids.	2003 Oct 8	14518986
Alpha,beta-unsaturated carbonyl compounds: induction of oxidative DNA damage in mammalian cells.	2003 Sep	12960416
Particle growth by acid-catalyzed heterogeneous reactions of organic carbonyls on preexisting aerosols.	2003 Sep 1	12967102
Two compounds from allelopathic rice accession and their inhibitory activity on weeds and fungal pathogens.	2004 Apr	15110693
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 Apr 2	15049624
Highly enantioselective Cu-catalysed asymmetric 1,4-addition of diphenylzinc to cyclohexenone.	2004 Aug 21	15306908
Brønsted acid-promoted cyclizations of siloxyalkynes with arenes and alkenes.	2004 Aug 25	15315407
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 Feb	14767145
Structure and expression of 12-oxophytodienoate reductase (subgroup I) genes in pea, and characterization of the oxidoreductase activities of their recombinant products.	2004 Feb	14727182
Novel enhancement of diastereoselectivity of [2 + 2] photocycloaddition of chiral cyclohexenones to ethylene by adding naphthalenes.	2004 Feb 6	14750805
Different reaction modes for the oxidative dimerization of epoxyquinols and epoxyquinones. Importance of intermolecular hydrogen-bonding.	2004 Mar 5	14987010
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 May	15131384
Synthesis and antinematodal activity of 3-n-alkylphenols.	2004 Nov	15564683
Protein thiol modification by 15-deoxy-Delta12,14-prostaglandin J2 addition in mesangial cells: role in the inhibition of pro-inflammatory genes.	2004 Nov	15317873
Highly enantioselective conjugate additions of potassium organotrifluoroborates to enones by use of monodentate phosphoramidite ligands.	2004 Nov 12	15527289
On the role of PIII ligands in the conjugate addition of diorganozinc derivatives to enones.	2004 Nov 19	15515102
A short route to enantiomerically pure benzophenanthridinone skeleton: synthesis of lactone analogues of narciclasine and lycoricidine.	2004 Oct 1	15387596
Oxygen-promoted palladium(II) catalysis: facile C(sp2)-C(sp2) bond formation via cross-coupling of alkenylboronic compounds and olefins.	2004 Oct 28	15496093
Catalytic enantioselective conjugate addition of trimethylsilylacetylene to 2-cyclohexen-1-one.	2004 Sep 16	15355058
Preparation of 2- and 4-arylmethyl N-substituted and N,N-disubstituted anilines via a "green", multicomponent reaction.	2005 Apr 14	15816743
Sequential aminodiene Diels-Alder approach to the ergoline skeleton.	2005 Aug 19	16095303
An exceptional P-H phosphonite: biphenyl-2,2'-bisfenchylchlorophosphite and derived ligands (BIFOPs) in enantioselective copper-catalyzed 1,4-additions.	2005 Aug 26	16542019
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 Dec	16330864
High stereoselectivity on low temperature Diels-Alder reactions.	2005 Dec 9	16542029
Three oxygenated cyclohexenone derivatives produced by an endophytic fungus.	2005 Feb	15725652
Parallel mechanistic studies on the counterion effect of manganese salen and porphyrin complexes on olefin epoxidation by iodosylarenes.	2005 Feb	15621274
Opening the 'black box': oscillations in organocuprate conjugate addition reactions.	2005 Feb 21	15700059
Synthesis of an analogue of the marine polypropionate tridachiahydropyrone.	2005 Feb 3	15673251
Structural assignment of Diels-Alder adducts: an experimental and theoretical approach.	2005 Jan 1	15556436
Role of active site residues and solvent in proton transfer and the modulation of flavin reduction potential in bacterial morphinone reductase.	2005 Jul 22	15905167
C-H...O hydrogen bonds in cyclohexenone reveal the spectroscopic behavior of Csp3-H and Csp2-H donors.	2005 Mar	15799475
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 Mar 18	15632179
Tandem Sakurai-aldol addition reactions as a route to structurally complex carbocycles.	2005 May 27	15903314
Probing the "additive effect" in the proline and proline hydroxamic acid catalyzed asymmetric addition of nitroalkanes to cyclic enones.	2005 Nov	16189834
Tetrahydropyran rings from a Mukaiyama-Michael cascade reaction.	2005 Nov 23	16287289
Facile preparation of a new BINAP-based building block, 5,5'-diiodoBINAP, and its synthetic application.	2005 Nov 25	16292868
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 Sep	16156787
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 Sep 15	16146412
Chiral binaphthyl-derived amine-thiourea organocatalyst-promoted asymmetric Morita-Baylis-Hillman reaction.	2005 Sep 15	16146410
Novel gamma-secretase inhibitors discovered by library screening of in-house synthetic natural product intermediates.	2006 Jul 15	16682195
A superior P-H phosphonite: asymmetric allylic substitutions with fenchol-based palladium catalysts.	2006 Mar 30	16573833
Synthesis of (+)-sch 642305 by a biomimetic transannular Michael reaction.	2006 Mar 30	16562872
Nucleophilic addition to (3-methylpentadienyl)iron(1+) cations: counterion control of regioselectivity; application to the enantioselective synthesis of 4,5-disubstituted cyclohexenones.	2006 May 10	16669637

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:25:16 GMT 2023` Edited by `admin` on `Fri Dec 15 17:25:16 GMT 2023`
Record UNII	445160R1U6
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

2-CYCLOHEXENONE

Systematic Name

English

NSC-59710

Code

English

CYCLOHEXEN-3-ONE

Systematic Name

English

3-OXOCYCLOHEXENE

Systematic Name

English

2-CYCLOHEXEN-1-ONE

Systematic Name

English

FEMA NO. 4517

Code

English

CYCLOHEXENE-1-ONE, 2-

Systematic Name

English

Classification Tree Code System Code

JECFA EVALUATION

2-CYCLOHEXENONE