| Revision as of 09:57, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 464305476 of page Benzopyran for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 07:43, 4 November 2024 edit Graeme Bartlett (talk | contribs)Administrators249,719 edits change to sane chemspider entry |
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{{More citations needed|date=January 2017}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Chembox |
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{{Chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 452828798 |
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| Watchedfields = changed |
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| ImageFile = 4H-Chromen.svg |
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| verifiedrevid = 464365209 |
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| Section1 = {{Chembox Identifiers |
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| ImageFile = 4H-Chromen.svg |
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| ChemSpiderID = 10651828 |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| index_label = 2''H''-chromene |
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| SMILES = |
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| CASNo_Ref = {{cascite|correct|PubChem}} |
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| StdInChI = 1S/C9H7O/c1-2-6-9-8(4-1)5-3-7-10-9/h1-7H |
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| CASNo = 254-04-6 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| Beilstein = 109871 |
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| StdInChIKey = QZHPTGXQGDFGEN-UHFFFAOYSA-N |
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| ChemSpiderID = 8856 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| PubChem = 9211 |
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| UNII = 7U3W6XRV5U |
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| ChEBI = 35601 |
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| SMILES = C1=Cc2ccccc2OC1 |
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| StdInChI =1S/C9H8O/c1-2-6-9-8(4-1)5-3-7-10-9/h1-6H,7H2 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = KYNSBQPICQTCGU-UHFFFAOYSA-N |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C = 9 |
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| C=9 | H=8 | O=1 |
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| H = 7 |
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| O = 1 |
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| ExactMass = 131.049689846 g mol<sup>-1</sup> |
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'''Benzopyran''' is a ] ] that results from the fusion of a ] ring to a ] ] ring. |
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According to current ] nomenclature, the name '''chromene''' used in previous recommendations is retained; however, systematic ‘benzo’ names, for example 2''H''-1-benzopyran, are ]s for chromene, isochromene, chromane, isochromane, and their chalcogen analogues.<ref name="IUPAC2013">{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | pages = P001–P004 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4| chapter = Front Matter }}</ref> 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 ]-like nomenclature. |
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Some benzopyrans have shown anticancerous activity '']''.<ref>{{cite journal|title=Mechanism of action of the third generation benzopyrans and evaluation of their broad anti-cancer activity in vitro and in vivo|journal=Scientific Reports|volume=8|issue=1|pages=5144|doi=10.1038/s41598-018-22882-w|pmid=29572477|pmc=5865165|year=2018|last1=Stevenson|first1=Alexander J|last2=Ager|first2=Eleanor I|last3=Proctor|first3=Martina A|last4=Škalamera|first4=Dubravka|last5=Heaton|first5=Andrew|last6=Brown|first6=David|last7=Gabrielli|first7=Brian G|bibcode=2018NatSR...8.5144S }}</ref> |
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The ] form of benzopyran is ]. The unpaired electron is delocalized over the whole benzopyran molecule, rendering it less reactive than one would expect otherwise. A similar example is the ] radical. Commonly, benzopyran is encountered in the reduced state, in which it is partially saturated with one hydrogen atom, introducing a tetrahedral CH<sub>2</sub> 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: |
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{|class=wikitable style="text-align:center;" |
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|+Structural isomers of chromene |
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| ]<br>2''H''-chromene<br>(2''H''-1-benzopyran) |
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| ]<br>4''H''-chromene<br>(4''H''-1-benzopyran) |
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| 5''H''-chromene |
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| 7''H''-chromene |
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| 8a''H''-chromene |
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{|class=wikitable style="text-align:center;" |
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|+Structural isomers of isochromene |
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| ]<br>1''H''-isochromene<br>(1''H''-2-benzopyran) |
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| ]<br>3''H''-isochromene<br>(3''H''-2-benzopyran) |
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<!-- are 4a''H''- or 6''H''- or 8''H''-isochromene known? --> |
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==See also== |
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*] |
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*] |
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==References== |
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{{reflist}} |
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{{Authority control}} |
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] |