Chalcone
- For the genus of grass skipper butterflies, see Chalcone (butterfly).
| Chalcone[1] | |
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1,3-Diphenyl-2-propen-1-one |
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Other names
Chalcone |
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| Identifiers | |
| CAS number | 94-41-7  , 614-47-1 ((E)-Chalcone) |
| PubChem | 637760 |
| ChemSpider | 6921 |
| ChEBI | CHEBI:27618 |
| Jmol-3D images | Image 1 |
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| 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 |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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.
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[edit] 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]
[edit] Chemical reactions
An example is the carbonyl reduction of chalcone by tributyltin hydride [5]:
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| Conjugate reduction chalcone |
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An asymmetric version of this reaction has also been developed.[6]
[edit] See also
[edit] References
- ^ Merck Index, 11th Edition, 2028.
- ^ Toda, F., et al., J. Chem. Soc. Perkin Trans. I, 1990, 3207.
- ^ Palleros, D. R., J. Chem. Educ., 81, 1345 (2004).
- ^ Comisar, C. M. and Savage, P. E. Green Chem., 6 (2004), 227 - 231. doi:10.1039/b314622g
- ^ 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.
- ^ 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.
