31853-85-7Relevant articles and documents
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Hachihama,Shono
, (1962)
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Synthesis of styrenes through the biocatalytic decarboxylation of trans-cinnamic acids by plant cell cultures
Takemoto,Achiwa
, p. 639 - 641 (2001)
A novel method for producing styrenes from trans-cinnamic acids was developed. When trans-cinnamic acid was incubated with plant cell cultures at room temperature, styrene was obtained. 4-Hydroxy-3-methoxystyrene (2a), 3-nitrostyrene (2f) and furan (2g) were synthesized quantitatively.
The bio-based phthalocyanine resins with high Tg and high char yield derived from vanillin
Wang, Caiyun,Shi, Manling,Fang, Linxuan,Dai, Menglu,Huang, Gang,Sun, Jing,Fang, Qiang
, (2021)
The conversion of bio-based vanillin into the heat-resistant polymers is investigated. Firstly, converting the aldehyde group of vanillin into a vinyl group obtained 2-methoxy-4-vinylphenol (S1), which was then treated with nitro-phthalonitrile to give 4-(2-methoxy-4-vinylphenoxy)phthalonitrile (S2). Secondly, thermal polymerization between S1 and S2 in a different molar ratio gave a series of vanillin–based phthalocyanine (V-PN) resins that display high char yield and high Tg. The best result was obtained when the molar ratio between S1 and S2 was 1–50 and the obtained V-PN resin displayed a char yield of up to 76%, a Tg over 400 °C. These data are much better than those of the widely used petroleum-based phthalocyanine resins, suggesting that these bio-based functional monomers derived from vanillin are suitable as the precursors for the fabrication of the ablation-resistant materials in the application of the aerospace industry.
Host attractants for red weevil, Rhynchophorus ferrugineus: Identification, electrophysiological activity, and laboratory bioassay
Gunawardena, Neelakanthi E.,Kern, Friedrich,Janssen, Edelgard,Meegoda, Chandana,Schaefer, Doris,Vostrowsky, Otto,Bestmann, Hans Juergen
, p. 425 - 437 (1998)
A steam distillate from the freshly cut young bark of coconut palm Cocos nucifera was analyzed by gas chromatography, combined gas chromatography-electroantennographic detection (GC-EAD) and GC-MS to detect host attractants for the curculionid weevil Rhynchophorus ferrugineus, one of the major coconut pests in Sri Lanka. A twin FID peak consisting of a minor and a major component was shown to possess electrophysiological (EAG) activity. The minor peak was identified as γ-nonanoic lactone 2, while the major peak was identified as 4-hydroxy-3-methoxystyrene 2. In an EAG assay the synthetic racemic nonanoic lactone 1 did not elicit a considerable response in the antenna of R. ferrugineus, whereas the laboratory synthesized 2 showed activity. In a laboratory bioassay using a Y-type olfactometer, synthetic 1 and 2 elicited moderate attractant properties to R. ferrugineus, whereas a 1:1 mixture of the compounds showed increased attraction over that of the individual compounds.
Synthesis of Lipophilic Antioxidants by a Lipase-B-Catalyzed Addition of Peracids to the Double Bond of 4-Vinyl-2-methoxyphenol
Zago, Erika,Durand, Erwann,Barouh, Nathalie,Lecomte, Jér?me,Villeneuve, Pierre,Aouf, Chahinez
, p. 9069 - 9075 (2015)
4-Vinyl guaiacol (2) was lipophilized through the electrophilic addition of peracids to its vinylic double bond. Those peracids were formed in situ, by the Candida antarctica lipase-B-assisted perhydrolysis of carboxylic acids ranging from C2 to C18, in hydrogen peroxide solution. The addition of peracids with 4-8 carbons in their alkyl chains led to the formation of two regioisomers, with the prevalence of hydroxyesters bearing a primary free hydroxyl (4c-4e). This prevalence became more pronounced when peracids with longer alkyl chains (C10-C18) were used. In this case, only isomers 4f-4h were formed. The antioxidant activity of the resulting hydroxyesters was assessed by means of the conjugated autoxidizable triene (CAT) assay, and it was found out that the 4-vinyl guaiacol antioxidant activity was significantly increased by grafting alkyl chains with 2-8 carbons.
Cross-Coupling Reactions with 2-Amino-/Acetylamino-Substituted 3-Iodo-1,4-naphthoquinones: Convenient Synthesis of Novel Alkenyl- And Alkynylnaphthoquinones and Derivatives
Demidoff, Felipe C.,Rodrigues Filho, Eduardo José P.,De Souza, Andréa Luzia F.,Netto, Chaquip D.,De Carvalho, Leandro L.
supporting information, p. 4097 - 4109 (2021/08/31)
Functionalized 1,4-naphthoquinones have been employed as versatile synthons in organic synthesis, in addition to presenting a large array of biological activities. Herein, the applications of 2-amino-/ acetylamino-substituted 3-iodo-1,4-naphthoquinones in cross-coupling reactions are described to successfully afford sixteen novel 3-styryl-1,4-naphthoquinones (amino-stilbene-quinone hybrids) and four 3-alkynyl-1,4-naphthoquinone in overall good yields. Interestingly, the alkynylated derivatives could be obtained from ligand- and Pd-free Cu I -mediated cross-coupling reactions, after extensive investigations to exclude Pd as a co-catalyst. Lastly, the desilanized terminal alkyne was subjected to click chemistry reactions to give two novel triazole-1,4-naphthoquinone hybrids.
Efficient synthesis of styrene derivatives through ethenolysis of renewable propenylbenzenes
Avenda?o Villarreal, Jesus A.,Delolo, Fábio G.,Granato, Artur V.,dos Santos, Eduardo N.
, (2021/06/03)
Functionalized styrenes were obtained by the ethenolysis of renewable 1-propenylbenzenes in a very efficient synthetic pathway. Some of the products are valuable food & flavor ingredients (4-vinylguaiacol) or locust pheromone (4-vinylanisole). The catalysts employed were ruthenium-alkylidene complexes bearing a N-heterocyclic carbene as a ligand, which bulkiness proved to be important for the catalysis output. The judicious choice the reaction conditions was critical to enable near quantitative yields under mild conditions in short reaction times. More strikingly, the catalyst load could be reduced to 0.01 mol%, keeping good conversion and selectivity.