Benzoxepin

Chemical compound From Wikipedia, the free encyclopedia

Benzoxepin (BOX) is an oxygen-containing bicyclic molecule consisting of an oxepin ring and a benzene ring. There are three isomers, varying in where the oxygen is positioned in the oxepin heterocycle relative where the benzene is fused to it.

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Benzoxepin
1-Benzoxepin
2-Benzoxepin
3-Benzoxepin
Identifiers
3D model (JSmol)
ChemSpider
  • 1-: InChI=1S/C10H8O/c1-2-7-10-9(5-1)6-3-4-8-11-10/h1-8H
    Key: LWZYUACNWRVDDJ-UHFFFAOYSA-N
  • 2-: InChI=1S/C10H8O/c1-2-5-10-8-11-7-3-6-9(10)4-1/h1-8H
    Key: GXFIQHWKGLBSLN-UHFFFAOYSA-N
  • 3-: InChI=1S/C10H8O/c1-2-4-10-6-8-11-7-5-9(10)3-1/h1-8H
    Key: APSZPCTXHHKIQO-UHFFFAOYSA-N
  • 1-: c1ccc2c(c1)C=CC=CO2
  • 2-: C1=CC2=CC=COC=C2C=C1
  • 3-: C1=CC=C2C=COC=CC2=C1
Related compounds
Other anions
 benzazepine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Natural occurrence

1-Benzoxepin, with the oxygen closest to the benzene, is found in the skeleton of several fungal metabolites.[1]

2-Benzoxepin skeletons are likewise found in fungal metabolites.[2]

3-Benzoxepin, with the oxygen furthest from the benzene, is the core of natural products such as perilloxin from Perilla frutescens (variant Acuta)[3] and tenual and tenucarb from Asphodeline tenuior.[4]

Structural formulas of perilloxin, tenual, and tenucarb
Structural formulas of perilloxin, tenual, and tenucarb

Derivatives

Certain substituted benzoxepins, like TFMBOX, are serotonergic psychedelics.[5][6][7]

References

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