Chroman
Structural formula | ||||||||||
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General | ||||||||||
Surname | Chroman | |||||||||
other names |
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Molecular formula | C 9 H 10 O | |||||||||
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properties | ||||||||||
Molar mass | 134.18 g mol −1 | |||||||||
Physical state |
liquid |
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density |
1.072 g cm −3 (20 ° C ) |
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Melting point |
4.8 ° C |
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boiling point |
215 ° C |
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Refractive index |
1.5444 (20 ° C) |
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safety instructions | ||||||||||
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As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C |
Chroman is a chemical compound in which a benzene ring with dihydropyran (an oxygen-containing heterocycle ) fused is. This is around the dihydro - derivative of chromenes .
The substance is an oil that smells like peppermint (see menthol ).
synthesis
Chromans can be produced, for example, by adding one equivalent of sodium borohydride to the corresponding ortho-3-ketoalkyl-phenol and subsequent work-up, or by catalyzed ring closure in a similar starting molecule with an activated double bond (this is where the ring closure takes place).
Derivatives
Naturally occurring derivatives of chroman are the catechins , Rotenoids , Tocopherols (vitamin E) and some of the cannabinoids .
Man- made chromans are z. B. the drugs cromakalim , nebivolol , ormeloxifene and troglitazone .
Also to be mentioned is 4- (2,2,4-trimethyl-4-chromanyl) phenol, the so-called Dianin compound (after Alexander Dianin ), which forms clathrates .
literature
- H. Beyer, W. Walter: Textbook of organic chemistry. 20th edition. Hirzel, Stuttgart 1984, pp. 743-746.
Individual evidence
- ↑ a b c d David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-130.
- ↑ H. Beyer, W. Walter: Textbook of organic chemistry. 20th edition. Hirzel, Stuttgart 1984, p. 743
- ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
- ↑ Chroman Synthesis. In: Organic Chemistry Portal. Retrieved November 17, 2018 .
- ↑ External identifiers or database links for 4- (2,2,4-trimethyl-4-chromanyl) phenol : CAS number: 472-41-3, EC number: 207-450-9, ECHA InfoCard : 100.006.775 , PubChem : 97788 , ChemSpider : 88264 , Wikidata : Q5271650 .
- ^ GO Lloyd, MW Bredenkamp, LJ Barbour: Enclathration of morpholinium cations by Dianin's compound: salt formation by partial host-to-guest proton transfer. In: Chemical communications (Cambridge, England). No. 32, 2005, pp. 4053-4055, PMID 16091797 .