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Benzoxepin

From Wikipedia, the free encyclopedia
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
Otheranions
benzazepine
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Benzoxepin (BOX) is an oxygen-containingbicyclic molecule consisting of anoxepin ring and abenzene ring. There are three isomers, varying in where the oxygen is positioned in the oxepinheterocycle relative where the benzene isfused to it.

Natural occurrence

[edit]

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 ofnatural products such asperilloxin fromPerilla frutescens (variant Acuta)[3] andtenual andtenucarb fromAsphodeline tenuior.[4]

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

Derivatives

[edit]

Certain substituted benzoxepins, likeTFMBOX, areserotonergic psychedelics.[5][6][7]

References

[edit]
  1. ^Wijnberg, Joannes B. R A.; van Veldhuizen, Albertus; Swarts, Henk J.; Frankland, Juliet C.; Field, Jim A. (1999). "Novel monochlorinated metabolites with a 1-benzoxepin skeleton fromMycena galopus".Tetrahedron Letters.40 (31):5767–5770.doi:10.1016/S0040-4039(99)01074-6.
  2. ^Lee, In-Kyoung; Jang, Yun-Woo; Kim, Young-Sook; Yu, Seung Hun; Lee, Kui Jae; Park, Seung-Moon; Oh, Byung-Taek; Chae, Jong-Chan; Yun, Bong-Sik (2009)."Xylarinols A and B, two new 2-benzoxepin derivatives from the fruiting bodies ofXylaria polymorpha".Journal of Antibiotics.62 (3):163–165.doi:10.1038/ja.2008.20.PMID 19148206.
  3. ^J. Liu; A. Steigel; E. Reininger; R. Bauer (2000), "Two New Prenylated 3-Benzoxepin Derivatives as Cyclooxygenase Inhibitors fromPerilla frutescens var. acuta",J. Nat. Prod.,63 (3):403–405,Bibcode:2000JNAtP..63..403L,doi:10.1021/np990362o,PMID 10757731
  4. ^A. Ulubelen; E. Tuzlaci; N. Atilan (1989), "Oxepine derivatives and anthraquinones fromAsphodeline tenuior andA. Taurica",Phytochemistry,28 (2):649–650,Bibcode:1989PChem..28..649U,doi:10.1016/0031-9422(89)80076-7
  5. ^Monte AP, Marona-Lewicka D, Cozzi NV, Nelson DL, Nichols DE (1995)."Conformationally Restricted Tetrahydro-1-Benzoxepin Analogs of Hallucinogenic Phenethylamines".Medicinal Chemistry Research.5 (651–663).
  6. ^Cozzi, Nicholas Vito (1994)."Pharmacological studies of some psychoactive phenylalkylamines: Entactogens, hallucinogens, and anorectics".ProQuest. Retrieved15 April 2025.
  7. ^"Structure-activity relationships of hallucinogens: Design, synthesis, and pharmacological evaluation of a series of conformationally restricted phenethylamines".ProQuest. Retrieved15 April 2025.
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