Chalcone

For the genus of grass skipper butterflies, see Chalcone (butterfly).
Chalcone[1]
IUPAC name

1,3-Diphenyl-2-propen-1-one
Other names

Chalcone
Chalkone
Benzylideneacetophenone
Phenyl styryl ketone
Identifiers
CAS number 94-41-7 Y, 
614-47-1 ((E)-Chalcone)
PubChem 637760
ChemSpider 6921 Y
ChEBI CHEBI:27618 Y
Jmol-3D images Image 1
Properties
Molecular formula C15H12O
Molar mass 208.26 g mol−1
Exact mass 208.088815
Density 1.071 g/cm3
Melting point

55–57 °C
Boiling point

345–348 °C
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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.

Contents

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.

This reaction has been found to work without any solvent at all - a solid-state reaction.[2] The reaction between substituted benzaldehydes and acetophenones has been used to demonstrate green chemistry in undergraduate chemistry education.[3] In a study investigating green chemistry synthesis, chalcones were also synthesized from the same starting materials in high temperature water (200 to 350 °C).[4]

Chemical reactions

An example is the carbonyl reduction of chalcone by tributyltin hydride [5]:

Conjugate reduction chalcone

An asymmetric version of this reaction has also been developed.[6]

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