Benzoxepin

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Benzoxepin
1 benzoxepine.svg
1-Benzoxepin
2 benzoxepine.svg
2-Benzoxepin
3 benzoxepine.svg
3-Benzoxepin
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • 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).

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.

Contents

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 Perilloxin+Tenual+Tenucarb.svg
Structural formulas of perilloxin, tenual, and tenucarb

Derivatives

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

References

  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 from Mycena 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 of Xylaria 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 from Perilla 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 from Asphodeline tenuior and A. 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. Retrieved 15 April 2025.
  7. ↑ "Structure-activity relationships of hallucinogens: Design, synthesis, and pharmacological evaluation of a series of conformationally restricted phenethylamines". ProQuest. Retrieved 15 April 2025.
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