Chroman

Structural formula
General
Surname	Chroman
other names	3,4-dihydro-2 H -1-benzopyran; 3,4-dihydro-2 H -chromene ( IUPAC );
Molecular formula	C 9 H 10 O
External identifiers / databases
PubChem	136319
Wikidata	Q1087547
properties
Molar mass	134.18 g mol −1
Physical state	liquid
density	1.072 g cm −3 (20 ° C )
Melting point	4.8 ° C
boiling point	215 ° C
Refractive index	1.5444 (20 ° C)
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	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 .

Dianin connection

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 .

[CRC90_3_174-1] 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.

[2] H. Beyer, W. Walter: Textbook of organic chemistry. 20th edition. Hirzel, Stuttgart 1984, p. 743

[NV-3] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[4] Chroman Synthesis. In: Organic Chemistry Portal. Retrieved November 17, 2018 .

[5] 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 .

[6] 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 .