The retroaldol reaction of chalcone

Guthrie, J. Peter; Cossar, John; Cullimore, Patricia A.; Kamkar, Nayyer Monshizadeh; Taylor, Kathleen F.

doi:10.1139/v83-449

Cited by 16 publications

(15 citation statements)

References 15 publications

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“…This reaction turned out to be somewhat more difficult to sort out, but we have now completed the kinetic analysis, and wish to report it in turn. This provides another example of a fully analyzed aldol condensation, to add to those we (1,(4)(5)(6)(7)(8)(9)(10) and others (1 1-14) have previously reported. To complete the analysis we had to develop computer programs allowing us to fit simultaneously multiple sets of data described by equations with common parameters.…”

Section: Introductionsupporting

confidence: 65%

The aldol condensation of acetone with acetophenone

Guthrie¹,

Wang²

1992

Can. J. Chem.

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). The kinetics and equilibria involved in the aldol condensation of acetone, acting as carbon acid, and acetophenone have been studied in aqueous alkaline solution. The enone isolated is the E isomer. The reactions are all first order in hydroxide, with rate and equilibrium constants (defined for E-enone as initial compound) of: k12 = (5. There is an equilibration of the two enones in base that is faster than hydration to the ketol: k14 = (3.14 f 0.8455To analyze the behavior of the enone:ketol equililbrium system in acid we simultaneously fitted analytical data for all three species (E-enone, Z-enone, and ketol) to a kinetic model, so that the rate constants were determined by the best fit to all of the data for an experiment. J . PETER GUTHRIE et XIAO-PING W A N G .Can [Traduit par la rkdaction]

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Section: Introductionsupporting

confidence: 65%

The aldol condensation of acetone with acetophenone

Guthrie¹,

Wang²

1992

Can. J. Chem.

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“…In designing carbonitrile-chalcone 4, we here make use of the Knoevenagel and retro-Knovenagel reactions (62) yielding the desired compound due to a reversible aldolization reaction (63) that has never been exploited in the antedrug field before. The biologically active compound, carbonitrile-chalcone 4, is readily hydrolyzed in aqueous media with a half-life of a few tens of min and yields vanillin and pCBA, which both serve as synthetic building blocks for the preparation of carbonitrile-chalcone 4.…”

Section: Discussionmentioning

confidence: 99%

An Antedrug of the CXCL12 Neutraligand Blocks Experimental Allergic Asthma without Systemic Effect in Mice

Daubeuf¹,

Hachet‐Haas²,

Gizzi³

et al. 2013

Journal of Biological Chemistry

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Background: The chemokine CXCL12 and its receptor CXCR4 are widely distributed and contribute to the physiopathology of inflammation.Results: Recruitment of eosinophils in the inflamed airway is selectively attenuated by short lived antagonists that block CXCL12-mediated activation of CXCR4.Conclusion: CXCL12/CXCR4 signaling regulates local leukocyte-mediated inflammation.Significance: Antedrugs of neutraligands allow dissecting the physiological role of chemokines, especially when expression occurs in multiple tissues.

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“…Although previously studied cases include both conjugated (5-9) and non-conjugated enones (2)(3)(4), there has been no detailed study of a cross-conjugated system where a ketone such as acetophenone acts as carbon nucleophile towards an unconjugated aldehyde or ketone in the aldol reaction. Chalcone has been studied (5,9) but in this case there is through-conjugation by the phenyl derived from benzaldehyde as well as cross-conjugation for the phenyl derived from acetophenone. The present case allows us to assess the effects of cross-conjugation uncomplicated by competing through-conjugation.…”

Section: Introductionmentioning

confidence: 99%

The aldol condensation of acetophenone with acetone

Guthrie¹,

Wang²

1991

Can. J. Chem.

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J. PETER GUTHR~E and X~AO-PING WANG. Can. J. Chem. 69, 339 (1991).The kinetics and equilibria involved in the aldol condensation of acetophenone, acting as carbon acid, and acetone have been studied in aqueous alkaline solution. The reactions are all first order in hydroxide, with rate and equilibrium constants (defined for enone as initial compound) of: k,, = 3. M-I. The series methylbutenal, mesityl oxide, and 3-methyl-l-phenyl-2-buten-lone can now be compared with regard to regularities and deviations from regularity. The related serie~cinnamaldeh~de, benzalacetone, and chalcone also provides insights into the behaviour of this system.

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The retroaldol reaction of chalcone

Cited by 16 publications

References 15 publications

The aldol condensation of acetone with acetophenone

The aldol condensation of acetone with acetophenone

An Antedrug of the CXCL12 Neutraligand Blocks Experimental Allergic Asthma without Systemic Effect in Mice

The aldol condensation of acetophenone with acetone

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