Oxepin: Difference between revisions

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	{{~~chembox~~		{{Chembox
			\| Verifiedfields = changed
⚫	\| verifiedrevid = ~~444955375~~
			\| Watchedfields = changed
⚫	\|~~ImageFile~~=Oxepine~~.svg~~
		⚫	\| verifiedrevid = 448773926
	\|ImageSize=100px
	\|~~IUPACName~~=Oxepine		\| ImageFileL1 = Oxepine.svg
			\| ImageSizeL1 = 110
⚫	\|OtherNames=Oxacycloheptatriene~~<br>Benzene oxide~~
			\| ImageAltL1 = Skeletal formula of oxepin
⚫	\|Section1= {{Chembox Identifiers
			\| ImageFileR1 = Oxepin-based-on-xtal-3D-bs-17.png
⚫	\| CASNo=291-70-3
			\| ImageSizeR1 = 140
⚫	\| PubChem=6451477
			\| ImageAltR1 = Ball-and-stick model of the oxepin molecule
⚫	\| SMILES=C1=CC=COC=C1
			\| ImageFile2 = Oxepin-based-on-xtal-3D-bs-17-side-view.png
			\| ImageSize2 = 140
		⚫	\| PIN=Oxepine
		⚫	\| OtherNames=Oxacycloheptatriene
		⚫	\|Section1={{Chembox Identifiers
			\| CASNo_Ref = {{cascite\|correct\|CAS}}
		⚫	\| CASNo=291-70-3
		⚫	\| PubChem=6451477
		⚫	\| SMILES=C1=CC=COC=C1
			\| UNII_Ref = {{fdacite\|correct\|FDA}}
			\| UNII = CVP5X85XX5
			\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
			\| ChemSpiderID = 4953942
			\| InChI = 1/C6H6O/c1-2-4-6-7-5-3-1/h1-6H
			\| InChIKey = ATYBXHSAIOKLMG-UHFFFAOYAS
			\| StdInChI_Ref = {{stdinchicite\|changed\|chemspider}}
			\| StdInChI = 1S/C6H6O/c1-2-4-6-7-5-3-1/h1-6H
			\| StdInChIKey_Ref = {{stdinchicite\|changed\|chemspider}}
			\| StdInChIKey = ATYBXHSAIOKLMG-UHFFFAOYSA-N
	}}		}}
	\|Section2= {{Chembox Properties		\|Section2={{Chembox Properties
			\| C=6 \| H=6 \| O=1
	\| Formula=C<sub>6</sub>H<sub>6</sub>O
			\| Appearance=
	\| MolarMass=94.11 g/mol
	\| ~~Appearance~~=		\| Density=
	\| ~~Density~~=		\| MeltingPt=
	\| ~~MeltingPt~~=		\| BoilingPt=
	\| ~~BoilingPt~~=		\| Solubility=
	\| Solubility=
	}}		}}
	\|Section3= {{Chembox Hazards		\|Section3={{Chembox Hazards
	\| MainHazards=		\| MainHazards=
	\| FlashPt=		\| FlashPt=
			\| AutoignitionPt =
	\| Autoignition=
			}}
			\| Section8 = {{Chembox Related
			\| Related_ref =
			\| OtherFunction =
			\| OtherFunction_label =
			\| OtherCompounds = ]<br/>]
	}}		}}
	}}		}}

	'''Oxepin''' is an oxygen-containing ] consisting of a seven-membered ring with three ]. It exists as an ] mixture with '''benzene oxide'''. The oxepin-benzene oxide system has ] bonds in which the equilibrium can be shifted to one extreme or the other by suitable substituents.<ref>{{cite journal \| doi = 10.1002/anie.196703851 \| journal = Angewandte Chemie International Edition in English \| title=Benzene Oxide-Oxepin Valence Tautomerism\| volume=6 \|issue=5 \|pages =385–401 \|author=E. Vogel and H. Günther \| year = 1967}}</ref> This compound is not aromatic.		'''Oxepin''' is an ]-containing ] consisting of a seven-membered ] with three ]s. The parent C<sub>6</sub>H<sub>6</sub>O exists as an ] mixture with '''benzene oxide'''.
			]

			The oxepin–benzene oxide equilibrium is affected by the ring ]s.<ref name=TautHist /> A related dimethyl derivative exists mainly as the oxepin isomer, an orange liquid.<ref name=Me2Synth />
	]<br style="clear:left;"/>

			Oxepin is an intermediate in the oxidation of ] by the ] (CYP).<ref name=Tox /> Other ]s are metabolites of the parent arene.

			:]

	==References==		==References==
			<references>
	{{commonscat\|Oxepins}}
			<ref name=Me2Synth>{{cite journal\|title=2,7-Dimethyloxepin\|first1=Leo A.\|last1=Paquette \|author1-link= Leo Paquette \|first2=J. H. \|last2=Barrett\|journal=Org. Synth.\|year=1969\|volume=49\|page=62\|doi=10.15227/orgsyn.049.0062}}</ref>
	{{Reflist}}
			<ref name=Tox>{{cite journal \|doi=10.1289/ehp.93100293 \|journal=Environmental Health Perspectives \|title=The Toxicology of Benzene \|volume=100 \|pages=293–306 \|first1=R.\|last1=Snyder \|first2= G. \|last2=Witz \|first3= B. D. \|last3=Goldstein \|year=1993 \|pmc=1519582 \|pmid=8354177\|jstor=3431535 \|doi-access=free }}</ref>
			<ref name=TautHist>{{cite journal \| doi = 10.1002/anie.196703851 \| journal = Angewandte Chemie International Edition in English \| title=Benzene Oxide–Oxepin Valence Tautomerism\| volume=6 \|issue=5 \|pages =385–401 \|first1=E.\|last1=Vogel \|first2=H.\|last2=Günther \| year = 1967}}</ref>
			</references>

			{{Commons category\|Oxepin}}
	]		]

	]
	]
	]
	]
	]
	]
	]

Latest revision as of 05:04, 12 November 2023

Oxepin

Names

Preferred IUPAC name Oxepine

Other names Oxacycloheptatriene

Identifiers

CAS Number

291-70-3

3D model (JSmol)

Interactive image

ChemSpider

4953942

PubChem CID

6451477

UNII

CVP5X85XX5

CompTox Dashboard (EPA)

DTXSID10183353

InChI

InChI=1S/C6H6O/c1-2-4-6-7-5-3-1/h1-6HKey: ATYBXHSAIOKLMG-UHFFFAOYSA-N
InChI=1/C6H6O/c1-2-4-6-7-5-3-1/h1-6HKey: ATYBXHSAIOKLMG-UHFFFAOYAS

SMILES

C1=CC=COC=C1

Properties

Chemical formula

C₆H₆O

Molar mass

94.113 g·mol

Related compounds

Cyclohexene oxide
Oxonane

Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).

N verify (what is ?) Infobox references

Chemical compound

Oxepin is an oxygen-containing heterocycle consisting of a seven-membered ring with three double bonds. The parent C₆H₆O exists as an equilibrium mixture with benzene oxide.

The oxepin–benzene oxide equilibrium is affected by the ring substituents. A related dimethyl derivative exists mainly as the oxepin isomer, an orange liquid.

Oxepin is an intermediate in the oxidation of benzene by the cytochrome P450 (CYP). Other arene oxides are metabolites of the parent arene.

References

Vogel, E.; Günther, H. (1967). "Benzene Oxide–Oxepin Valence Tautomerism". Angewandte Chemie International Edition in English. 6 (5): 385–401. doi:10.1002/anie.196703851.
Paquette, Leo A.; Barrett, J. H. (1969). "2,7-Dimethyloxepin". Org. Synth. 49: 62. doi:10.15227/orgsyn.049.0062.
Snyder, R.; Witz, G.; Goldstein, B. D. (1993). "The Toxicology of Benzene". Environmental Health Perspectives. 100: 293–306. doi:10.1289/ehp.93100293. JSTOR 3431535. PMC 1519582. PMID 8354177.

Category:

Oxepines