- DIRECT AND MEDIATED EFFECTS ON Bactrocera oleae (GMELIN) (DIPTERA; TEPHRITIDAE) OF NATURAL POLYPHENOLS AND SOME OF RELATED SYNTHETIC COMPOUNDS: STRUCTURE-ACTIVITY RELATIONSHIPS
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Among the main polyphenols occurring in olive oil vegetation waters (VW), catechol showed the most deterrent action on the oviposition of Bactrocera oleae (Gmelin); 4-methylcatechol was less active, whereas hydroxytyrosol and tyrosol were inactive. In con
- Capasso, Renato,Evidente, Antonio,Tremblay, Ermenegildo,Sala, Andrea,Santoro, Carmine,et al.
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- Preparation method for synthesis of phenolic ester through thiocarboxylic acid mediated visible light catalyzed phenol acylation reaction
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The invention discloses a preparation method for synthesis of phenolic ester through a thiocarboxylic acid mediated visible light catalyzed phenol acylation reaction. Thiocarboxylic acid compounds andphenol compounds are subjected to a site specific reaction under certain conditions to produce phenolic ester compounds, wherein the certain conditions are as follows: under the conditions of normaltemperature, normal pressure and visible light, K2CO3 is used as an alkaline catalyst, terpyridyl ruthenium dichloride hexahydrate is used as a photosensitizer and acetonitrile is used as a reaction solvent. Synthesis of phenolic ester under catalysis of visible light is realized, thiocarboxylic acid is used as an acylation reagent, and the site specific phenol esterification reaction is realizedefficiently under mild conditions of normal temperature, normal pressure and visible light. The method has mild reaction conditions, large substrate functional group tolerance, high applicability andhigh yield, and an efficient, reliable and economical preparation method is provided for synthesis of phenolic ester.
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Paragraph 0079; 0080; 0109; 0110; 0111
(2018/07/30)
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- Regioselective hydrosilylation of epoxides catalysed by nickel(II) hydrido complexes
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Bench-stable nickel fluoride complexes bearing NNN pincer ligands have been employed as precursors for the regioselective hydrosilylation of epoxides at room temperature. A nickel hydride assisted epoxide opening is followed by the cleavage of the newly formed nickel oxygen bond by σ-bond metathesis with a silane.
- Wenz, Jan,Wadepohl, Hubert,Gade, Lutz H.
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supporting information
p. 4308 - 4311
(2017/04/21)
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- A selective and mild glycosylation method of natural phenolic alcohols
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Several bioactive natural p-hydroxyphenylalkyl β-D-glucopyranosides, such as vanillyl β-D-glucopyranoside, salidroside and isoconiferin, and their glycosyl analogues were prepared by a simple reaction sequence. The highly efficient synthetic approach was achieved by utilizing acetylated glycosyl bromides as well as aromatic moieties and mild glycosylation promoters. The aglycones, p-O-acetylated arylalkyl alcohols, were prepared by the reduction of the corresponding acetylated aldehydes or acids. Various stereoselective 1,2-trans-O-glycosylation methods were studied, including the DDQ-iodine or ZnO-ZnCl2 catalyst combination. Among them, ZnO-iodine has been identified as a new glycosylation promoter and successfully applied to the stereoselective glycoside synthesis. The final products were obtained by conventional Zemplén deacetylation.
- Mastihubová, Mária,Poláková, Monika
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supporting information
p. 524 - 530
(2016/04/08)
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- Selective acylation of the phenolic hydroxyl of (hydroxyalkyl)phenols by using vinyl carboxylates as acyl donors in the presence of rubidium fluoride
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Highly selective acylation of the phenolic hydroxy group can be achieved with (hydroxyalkyl)phenols carrying both alcoholic and phenolic hydroxyls by the use of vinyl carboxylates as acyl donors in the presence of rubidium fluoride.
- Miyazawa, Toshifumi,Yamamoto, Masato,Danjo, Hiroshi
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p. 1351 - 1354
(2013/10/01)
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- Development of a kilogram-scale synthesis of salidroside and its analogs
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An efficient, safe, and viable process has been developed for large-scale preparation of salidroside, a natural product. The process consists of two chemical steps, which produce the salidroside on a multikilogram scale with 72% overall yield and >98% purity.A series of novel salidroside analogs were prepared according to the same method. Taylor & Francis Group, LLC.
- Shi, Tianyao,Chen, Hui,Jing, Linlin,Liu, Xueying,Sun, Xiaoli,Jiang, Ru
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experimental part
p. 2594 - 2600
(2011/08/07)
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- Understanding the exceptional hydrogen-atom donor characteristics of water in TiIII-mediated free-radical chemistry
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In recent years solid evidence of HAT reactions involving water as hydrogen atom source have been presented. In this work we demonstrate that the efficiency of titanocene(III) aqua complexes as an unique class of HAT reagents is based on two key features: (a) excellent binding capabilities of water toward titanocene(III) complexes and (b) a low activation energy for the HAT step. The theory has predictive capabilities fitting well with the experimental results and may aid to find more examples of this remarkable radical reaction.
- Paradas, Miguel,Campana, Araceli G.,Jimenez, Tania,Robles, Rafael,Oltra, J. Enrique,Bunuel, Elena,Justicia, Jose,Cardenas, Diego J.,Cuerva, Juan M.
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supporting information; experimental part
p. 12748 - 12756
(2010/10/21)
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- Radical reduction of epoxides using a titanocene(III)/water system: Synthesis of β-deuterated alcohols and their use as internal standards in food analysis
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We describe a comprehensive study into the Cp2TiCl-mediated reductive epoxide ring opening using either water as a hydrogen source or deuterium oxide as a deuterium source. The remarkable chemical profile of this reaction allows access to alcohols with anti-Markovnikov regiochemistry from different epoxides. The use of D2O as a deuterium source leads to an efficient synthesis of β-deuterated alcohols, including a deuterated sample of tyrosol, a bioactive compound contained in the leaves of the olive, which was successfully applied as an internal standard in food analysis.
- Jimenez, Tania,Campana, Araceli G.,Bazdi, Btissam,Paradas, Miguel,Arraez-Roman, David,Segura-Carretero, Antonio,Fernandez-Gutierrez, Alberto,Oltra, J. Enrique,Robles, Rafael,Justicia, Jose,Cuerva, Juan M.
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experimental part
p. 4288 - 4295
(2010/10/21)
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- Microwave-accelerated selective acylation of (hydroxyalkyl)phenols using acid chlorides
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Highly selective acylation of the alcoholic hydroxy group can be achieved with (hydroxyalkyl)phenols carrying both alcoholic and phenolic hydroxyls by the use of the most common acylating agents, acid chlorides, under microwave irradiation. Copyright Tayl
- Miyazawa, Toshifumi,Yamamoto, Masato,Maeda, Yuki
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experimental part
p. 1092 - 1099
(2009/09/06)
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- Biological activity of acetylated phenolic compounds
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In recent years an effort has been made to isolate and identify biologically active compounds that are included in the Mediterranean diet. The existence of naturally occurring acetylated phenolics, as well as studies with synthetic ones, provide evidence that acetyl groups could be correlated with their biological activity. Platelet activating factor (PAF) is implicated in atherosclerosis, whereas its inhibitors seem to play a protective role against cardiovascular disease. The aim of this study was to examine the biological activity of resveratrol and tyrosol and their acetylated derivatives as inhibitors of PAF-induced washed rabbit platelet aggregation. Acetylation of resveratrol and tyrosol was performed, and separation was achieved by HPLC. Acetylated derivatives were identified by negative mass spectrometry. The data showed that tyrosol and its monoacetylated derivatives act as PAF inhibitors, whereas diacetylated derivatives induce platelet aggregation. Resveratrol and its mono- and triacetylated derivatives exert similar inhibitory activity, whereas the diacetylated ones are more potent inhibitors. In conclusion, acetylated phenolics exert the same or even higher antithrombotic activity compared to the biological activity of the initial one.
- Fragopoulou, Elizabeth,Nomikos, Tzortzis,Karantonis, Haralabos C.,Apostolakis, Constantinos,Pliakis, Emmanuel,Samiotaki, Martina,Panayotou, George,Antonopoulou, Smaragdi
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- Highly efficient and versatile acetylation of alcohols catalyzed by cerium(III) triflate
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Cerium(III) triflate is a powerful catalyst for the acetylation of alcohols. The reaction works well for a large variety of simple and functionalized alcohols, without isomerisation of chiral centres. Changes of hydroxyl protective groups are possible in a one-pot procedure. The catalyst can be easily recycled.
- Dalpozzo, Renato,De Nino, Antonio,Maiuolo, Loredana,Procopio, Antonio,Nardi, Monica,Bartoli, Giuseppe,Romeo, Roberto
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p. 5621 - 5624
(2007/10/03)
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- Thiazolidinedione, oxazolidinedione and oxadiazolidinedione derivatives
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Novel thiazolidinedione, oxazolidinedione and oxadiazolidinedione derivatives, process for their manufacture, pharmaceutical preparations containing them and the use of the compounds in conditions associated with insulin resistance.
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- Dendroid peptide structural mimetics of ω-conotoxin MVIIA based on a 2(1H)-quinolinone core
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Three mimetics of the peptide ω-Conotoxin MVIIA have been synthesised following the dendroid approach. The three key central amino acids of the natural peptide are mimicked by phenylguanidine (arginine), isopentyl (leucine) and aryl alcohol (tyrosine) att
- Guo, Zhao-Xia,Cammidge, Andrew N.,Horwell, David C.
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p. 5169 - 5175
(2007/10/03)
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- A mild and selective cleavage of tritylethers by cerium(III) chloride
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Trityl ethers are selectively cleaved by cerium(III) chloride in high yields in refluxing acetonitrile under neutral reaction conditions. The method is compatible with other acid sensitive functional groups like acetonide, acetate, benzoate, BOC, Cbz, benzyl, TBDPS, PMB, allyl, methyl and tetrahydropyranyl ethers present in the molecule.
- Yadav,Subba Reddy
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p. 1275 - 1276
(2007/10/03)
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- Synthesis of 13C-labeled possible intermediates in the biosynthesis of phenylethanoid derivatives, cornoside and rengyosides
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In order to clarify the biosynthetic pathway of C6-C2 unit compounds containing salidroside, cornoside, and rengyosides A and B in oleaceous plants, 13C-labeled putative precursors, 4-hydroxyphenylethanol, salidroside and cornoside, were prepared.
- Kuwajima, Hiroshi,Takai, Yoshitaka,Takaishi, Kiyokazu,Inoue, Kenichiro
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p. 581 - 586
(2007/10/03)
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- An Extremely Powerful Acylation Reaction of Alcohols with Acid Anhydrides Catalyzed by Trimethylsilyl Trifluoromethanesulfonate
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Trimethylsilyl trifluoromethanesulfonate is an excellent catalyst for the acylation of alcohols with acid anhydrides. Highly functionalized primary, secondary, tertiary, and allylic alcohols, and phenols, were acylated cleanly and efficiently and in a fraction of the time used under the standard DMAP conditions.
- Procopiou, Panayiotis A.,Baugh, Simon P.D.,Flack, Stephen S.,Inglis, Graham G.A.
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p. 2342 - 2347
(2007/10/03)
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- Production of 4-hydroxyphenethyl alcohol
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A method for producing 4-hydroxyphenethyl alcohol by epoxidizing 4-acetoxystyrene with a percaboxylic acid to produce 4-acetoxyphenyl oxirane; and catalytically hydrogenating the 4-acetoxyphenyl oxirane with hydrogen to produce 4-acetoxyphenethyl alcohol; and saponifying or transesterifying the 4-acetoxyphenethyl alcohol to produce 4-hydroxyphenethyl alcohol.
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- SELECTIVE ACYLATIONS OF AMINOPHENOLS AND HYDROXYALKYLPHENOLS WITH 1-ACETYL-v-TRIAZOLOPYRIDINE.
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The title triazolide serves as a convenient reagent for highly chemoselective acetylations of aminophenols and hydroxyalkylphenols.
- Paradisi, Mario Paglialunga,Zecchini, Giampiero Pagani,Torrini, Ines
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p. 5029 - 5032
(2007/10/02)
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