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Chalcone

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For the genus of grass skipper butterflies, see Chalcone (butterfly).
Chalcone
Names
IUPAC name 1,3-Diphenyl-2-propen-1-one
Other names Chalcone
Chalkone
Benzylideneacetophenone
Phenyl styryl ketone
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.002.119 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C15H12O/c16-15(14-9-5-2-6-10-14)12-11-13-7-3-1-4-8-13/h1-12HKey: DQFBYFPFKXHELB-UHFFFAOYSA-N
  • InChI=1/C15H12O/c16-15(14-9-5-2-6-10-14)12-11-13-7-3-1-4-8-13/h1-12HKey: DQFBYFPFKXHELB-UHFFFAOYAP
SMILES
  • O=C(C=Cc1ccccc1)c2ccccc2
Properties
Chemical formula C15H12O
Molar mass 208.26 g/mol
Density 1.071 g/cm
Melting point 55–57 °C
Boiling point 345-348 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Chalcone is an aromatic ketone and an enone that forms the central core for a variety of important biological compounds, which are known collectively as chalcones or chalconoids.

Chemical synthesis

Chalcones can be prepared by an aldol condensation between a benzaldehyde and an acetophenone in the presence of sodium hydroxide as a catalyst.

prepration of chalcone

This reaction has been found to work without any solvent at all - a solid-state reaction. The reaction between substituted benzaldehydes and acetophenones has been used to demonstrate green chemistry in undergraduate chemistry education. In a study investigating green chemistry synthesis, chalcones were also synthesized from the same starting materials in high temperature water (200 to 350 °C).

Chemical reactions

An example is the carbonyl reduction of chalcone by tributyltin hydride :

Conjugate reduction chalcone
Conjugate reduction chalcone
Conjugate reduction chalcone

An asymmetric version of this reaction has also been developed .

See also

References

  1. Merck Index, 11th Edition, 2028.
  2. Toda, F., et al., J. Chem. Soc. Perkin Trans. I, 1990, 3207.
  3. Palleros, D. R., J. Chem. Educ., 81, 1345 (2004).
  4. Comisar, C. M. and Savage, P. E. Green Chem., 6 (2004), 227 - 231. doi:10.1039/b314622g
  5. Leusink, A.J.; Noltes, J.G. (1966). "Reaction of organotin hydrides with α,β-unsaturated ketones". Tetrahedron Letters. 7 (20): 2221. doi:10.1016/S0040-4039(00)72405-1.
  6. Moritani, Yasunori; Appella, Daniel H.; Jurkauskas, Valdas; Buchwald, Stephen L. (2000). "Synthesis of β-Alkyl Cyclopentanones in High Enantiomeric Excess via Copper-Catalyzed Asymmetric Conjugate Reduction". Journal of the American Chemical Society. 122 (28): 6797. doi:10.1021/ja0009525.

External links

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