99337-60-7Relevant articles and documents
Effect of Fluorination on Skin Sensitization Potential and Fragrant Properties of Cinnamyl Compounds
Charpentier, Julie,Emter, Roger,Koch, Heinz,Lelièvre, Dominique,Pannecoucke, Xavier,Couve-Bonnaire, Samuel,Natsch, Andreas,Bombrun, Agnes
, (2018/04/27)
A series of three α- and three β-fluorinated representatives of the family of cinnamate-derived odorants (cinnamaldehyde (1), cinnamyl alcohol (2), and ethyl cinnamate (3)) as used as fragrance ingredients is described. Olfactive evaluation shows that the
Gold-Catalyzed Hydrofluorination of Electron-Deficient Alkynes: Stereoselective Synthesis of β-Fluoro Michael Acceptors
O'Connor, Thomas J.,Toste, F. Dean
, p. 5947 - 5951 (2018/07/24)
The gold(I)-catalyzed, stereoselective hydrofluorination of electron-deficient alkynes with triethylamine trihydrogen fluoride (Et3N·3HF) is described. Fluorinated α,β-unsaturated aldehydes, amides, esters, ketones, and nitriles were isolated i
Stereoselective One-Pot Sequential Dehydrochlorination/trans-Hydrofluorination Reaction of β-Chloro-α,β-unsaturated Aldehydes or Ketones: Facile Access to (Z)-β-Fluoro-β-arylenals/β-Fluoro-β-arylenones
Zhang, Jingli,Liu, Liran,Duan, Junxin,Gu, Lianghu,Chen, Bifeng,Sun, Taolei,Gong, Yuefa
supporting information, p. 4348 - 4358 (2017/12/26)
The monofluoroalkene substructure shows a high potential as a fluorinated synthon in organic synthesis. However, control of the Z/E stereoselectivity of multi-substituted monofluoroalkene products in one-pot reactions still remains a challenge. An unprecedented one-pot approach for the highly regio- and stereoselective preparation of functionalized (Z)-β-monofluoro tri-substituted alkenes from readily available β-chloro-α,β-unsaturated aldehydes or ketones has been explored. Mechanistic studies demonstrated that the reaction is initiated by dehydrochlorination of the substrates to give alkynyl aldehydes/ketones, followed by their trans-hydrofluorination. It is worth mentioning that a fluorinating reagent with suitable basicity and nucleophilicity plays a key role in promoting the formation of (Z)-β-fluoro-β-aryl tri-substituted monofluoroalkenes. (Figure presented.).
Characterization of the monolignol oxidoreductase AtBBE-like protein 15 L182V for biocatalytic applications
Pils, Sabine,Schnabl, Kordula,Wallner, Silvia,Daniel, Bastian,Macheroux, Peter,Kljajic, Marko,Kupresanin, Nina,Breinbauer, Rolf,Fuchs, Michael,Rocha, Raquel,Schrittwieser, Joerg H.,Kroutil, Wolfgang
, p. S6 - S14 (2018/04/05)
Monolignol oxidoreductases from the berberine bridge enzyme-like (BBE-like) protein family (pfam 08031) catalyze the oxidation of monolignols to the corresponding aldehydes. In this report, we explore the potential of a monolignol oxidoreductase from Arabidopsis thaliana (AtBBE-like protein 15) as biocatalyst for oxidative reactions. For this study we employed a variant with enhanced reactivity towards oxygen, which was obtained by a single amino acid exchange (L182V). The pH and temperature optima of the purified AtBBE-like protein 15 L182V were determined as well as the tolerance toward organic co-solvents; furthermore the substrate scope was characterized. The enzyme has a temperature optimum of 50 °C and retains more than 50% activity between pH 5 and pH 10 within 5 min. The enzyme shows increased activity in the presence of various co-solvents (10–50% v/v), including acetonitrile, 2-propanol, 1,4-dioxane, and dimethyl sulfoxide. Primary benzylic and primary or secondary allylic alcohols were accepted as substrates. The enantioselectivity E in the oxidation of secondary alcohols was good to excellent (E>34 to?>200).
Mono-hydrofluorination of Electrophilic Alkynes by the Liquid Bishasic CsF-H2O-DMF System (DMF = N,N-dimethylformamide)
Gorgues, Alain,Stephan, Dominique,Cousseau, Jack
, p. 1493 - 1494 (2007/10/02)
CsF induces the addition of HF in fair yields to activated acetylenic triple bonds in a DMF-water bishasic medium (DMF = N,N-dimethylformamide); in a homogeneous DMF-water mixture, no addition is observed.
Tetrabutylammonium and polymer-supported dihydrogentrifluoride: new reagents for the hydrofluorination of activated acetylenic bonds
Cousseau, Jack,Albert, Patrice
, p. 910 - 915 (2007/10/02)
Tetrabutylammonium and polymer-supported dihydrogentrifluoride are easily prepared by a phase-transfer procedure from the corresponding fluoride salts.These stable new dihydrogentrifluoride salts allow the addition of HF under mild conditions to carbon-ca
Tetrabutylammonium and Polymer-supported Dihydrogentrifluoride: New Hydrofluorinating Reagents for Electrophilic Alkynes
Albert, Patrice,Cousseau, Jack
, p. 961 - 962 (2007/10/02)
Tetrabutylammonium and polymer-supported dihydrogentrifluoride are readily accessible reagents which allow addition of HF to activated carbon-carbon triple bonds, thus leading to functional fluoroalkenes in good yields.