Chalcone

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For the butterflies, see Chalcone (skipper).
Chalcone[1]
Chalcone.svg
Identifiers
CAS number 94-41-7 YesY
614-47-1 ((E)-Chalcone)
PubChem 637760
ChemSpider 6921 YesY
ChEBI CHEBI:27618 YesY
Jmol-3D images Image 1
Properties
Molecular formula C15H12O
Molar mass 208.26 g mol−1
Density 1.071 g/cm3
Melting point 55 to 57 °C (131 to 135 °F; 328 to 330 K)
Boiling point 345 to 348 °C (653 to 658 °F; 618 to 621 K)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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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. Benzylideneacetophenone is the parent member of the chalcone series. The alternative name given to chalcone are phenyl styryl ketone, benzalacetophenone, β-phenylacrylophenone, ɣ-oxo-α,ɣ-diphenyl-α-propylene and α-phenyl-β-benzoylethylene.

Chemical properties[edit]

Chalcones have two absorption maxima at 280 nm and 340 nm.[2]

Chemical reactions[edit]

Synthesis[edit]

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

preparation of chalcone

This reaction has been found to work without any solvent at all - a solid-state reaction.[3] The reaction between substituted benzaldehydes and acetophenones has been used to demonstrate green chemistry in undergraduate chemistry education.[4] In a study investigating green chemistry synthesis, chalcones were also synthesized from the same starting materials in high temperature water (200 to 350 °C).[5]

Alternatively, the substituted chalcones were synthesised by piperidine mediated condensation to avoid side reactions such as multiple condensations,polymerizations, and rearrangements.[6]

Other reactions[edit]

An example is the carbonyl reduction of chalcone by tributyltin hydride:[7]

Conjugate reduction of chalcone

An enantioselective version of this reaction has also been developed.[8]

See also[edit]

References[edit]

  1. ^ Merck Index, 11th Edition, 2028.
  2. ^ Photochemistry of chalcone and the application of chalcone-derivatives in photo-alignment layer of liquid crystal display. Dong-mee Song, Kyoung-hoon Jung, Ji-hye Moon and Dong-myung Shin, Optical Materials, 2002, volume 21, pages 667–671, doi:10.1016/S0925-3467(02)00220-3
  3. ^ Toda, F., et al., J. Chem. Soc. Perkin Trans. I, 1990, 3207.
  4. ^ Palleros, D. R., J. Chem. Educ., 81, 1345 (2004).
  5. ^ Comisar, C. M. and Savage, P. E. Green Chem., 6 (2004), 227 - 231. doi:10.1039/b314622g
  6. ^ P Venkatesan and S Sumathi, "Piperidine Mediated Synthesis of N-Heterocyclic Chalcones and Their Antibacterial Activity", J. Heterocyclic Chem., 47, 81 (2010).
  7. ^ 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. 
  8. ^ 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[edit]