Benzopyran

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Benzopyran
4H-Chromen.svg
Identifiers
3D model (JSmol)
109871
ChEBI
ChemSpider
PubChem CID
UNII
  • InChI=1S/C9H7O/c1-2-6-9-8(4-1)5-3-7-10-9/h1-7H Yes check.svgY
    Key: QZHPTGXQGDFGEN-UHFFFAOYSA-N Yes check.svgY
  • c12ccccc1CC=CO2
Properties
C9H8O
Molar mass 132.162 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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. [1] 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 . [2]

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-Chromen.svg
2H-chromene
(2H-1-benzopyran)
4H-Chromen.svg
4H-chromene
(4H-1-benzopyran)
5H-chromene7H-chromene
8aH-chromene
Structural isomers of isochromene
1H-Isochromen.svg
1H-isochromene
(1H-2-benzopyran)
3H-Isochromen.svg
3H-isochromene
(3H-2-benzopyran)

See also

Related Research Articles

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<span class="mw-page-title-main">Cahn–Ingold–Prelog priority rules</span> Naming convention for stereoisomers of molecules

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<span class="mw-page-title-main">Functional group</span> Set of atoms in a molecule which augment its chemical and/or physical properties

In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest of the molecule's composition. This enables systematic prediction of chemical reactions and behavior of chemical compounds and the design of chemical synthesis. The reactivity of a functional group can be modified by other functional groups nearby. Functional group interconversion can be used in retrosynthetic analysis to plan organic synthesis.

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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.