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Benzopyran

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Benzopyran
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 109871
ChEBI
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C9H8O/c1-2-6-9-8(4-1)5-3-7-10-9/h1-6H,7H2Key: KYNSBQPICQTCGU-UHFFFAOYSA-N
SMILES
  • 2H-chromene: C1=Cc2ccccc2OC1
Properties
Chemical formula C9H8O
Molar mass 132.162 g·mol
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

Benzopyran is a polycyclic organic compound that results from the fusion of a benzene ring to a heterocyclic pyran ring.

According to current IUPAC nomenclature, the name chromene used in previous recommendations is retained; however, systematic ‘benzo’ names, for example 2H-1-benzopyran, are preferred IUPAC names for chromene, isochromene, chromane, isochromane, and their chalcogen analogues. There are two isomers of benzopyran that vary by the orientation of the fusion of the two rings compared to the oxygen, resulting in 1-benzopyran (chromene) and 2-benzopyran (isochromene)—the number denotes where the oxygen atom is located by standard naphthalene-like nomenclature.

Some benzopyrans have shown anticancerous activity in vitro.

The radical form of benzopyran is paramagnetic. The unpaired electron is delocalized over the whole benzopyran molecule, rendering it less reactive than one would expect otherwise. A similar example is the cyclopentadienyl radical. Commonly, benzopyran is encountered in the reduced state, in which it is partially saturated with one hydrogen atom, introducing a tetrahedral CH2 group in the pyran ring. Therefore, there are many structural isomers owing to the multiple possible positions of the oxygen atom and the tetrahedral carbon atom:

Structural isomers of chromene

2H-chromene
(2H-1-benzopyran)
4H-chromene
(4H-1-benzopyran)
5H-chromene 7H-chromene
8aH-chromene
Structural isomers of isochromene

1H-isochromene
(1H-2-benzopyran)
3H-isochromene
(3H-2-benzopyran)

See also

References

  1. "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. P001–P004. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  2. Stevenson, Alexander J; Ager, Eleanor I; Proctor, Martina A; Škalamera, Dubravka; Heaton, Andrew; Brown, David; Gabrielli, Brian G (2018). "Mechanism of action of the third generation benzopyrans and evaluation of their broad anti-cancer activity in vitro and in vivo". Scientific Reports. 8 (1): 5144. Bibcode:2018NatSR...8.5144S. doi:10.1038/s41598-018-22882-w. PMC 5865165. PMID 29572477.
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