- Synthesis and Catalytic Activity of Quaternary Ammonium Salts Containing gem-Dichlorocyclopropane and 1,3-Dioxolane Fragments
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Abstract: Quaternary ammonium salts containing gem-dichlorocyclopropane and 1,3-dioxolane groups were synthesized in high yield. The reactions of dichlorocarbonation of styrene and O-alkylation of 2,2-dimethyl-4-hydroxymethyl-1,3-dioxolane in the presence of quaternary ammonium salts were studied. It was established that in the O-alkylation reaction, compounds containing cycloacetal and allyl moieties have the maximum efficiency in the series of catalysts studied. The structures of the isolated salts were proved by 1H and 13C NMR spectroscopy.
- Raskil’dina, G. Z.,Sakhabutdinova, G. N.,Yakovenko, E. A.,Zlotskii, S. S.
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p. 967 - 972
(2020/08/24)
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- Condensation of 1,2,4-Butanetriol with Carbonyl Compounds and Reactions of Hydroxyalkyl-1,3-dioxacyclanes
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A mixture of isomers of 2-(1,3-dioxolan-4-yl)ethanol and 1,3-dioxan-4-ylmethanol was prepared by reaction of 1,2,4-butanetriol with paraformaldehyde. This mixture was subjected to O-alkylation, O-acylation, condensation with phenyl isocyanate, and substitution of OH groups for Cl. The relative activity of acetone derivatives of glycerol and 1,2,4-butanetriol in reactions with allyl chloride and benzyl chloride was estimated.
- Raskil’dina,Borisova, Yu. G.,Zlotskii
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p. 1601 - 1605
(2018/11/10)
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- Hybrid Fluorinated and Hydrogenated Double-Chain Surfactants for Handling Membrane Proteins
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Two hybrid fluorinated double-chain surfactants with a diglucosylated polar head were synthesized. The apolar domain consists of a perfluorohexyl main chain and a butyl hydrogenated branch as a side chain. They were found to self-assemble into small micel
- Legrand, Frderic,Breyton, Ccile,Guillet, Pierre,Ebel, Christine,Durand, Grgory
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p. 681 - 688
(2016/01/25)
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- Selective functionalization of the primary hydroxy group in triols
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A procedure was suggested for preparing functionally substituted 1,2-diols by O-alkylation of hydroxyalkyl-1,3-dioxacyclanes with alkyl halides, followed by acid hydrolysis. The conditions for selective cleavage of the ethers obtained were found. (2,2-Dimethyl-1,3-dioxolan-4-yl)methyl benzoate under the conditions of acid deacetalization undergoes saponification of the ester group.
- Raskil'Dina,Valiev,Sultanova,Zlotskii
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p. 1599 - 1604
(2016/02/18)
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- Discovery of lipids from B. longum subsp. infantis using whole cell MALDI analysis
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Bifidobacteria are dominant members of the microbial community in the intestinal tract of infants, and studies have shown that glycolipids extracted from the cell surface of these bacteria elicit beneficial immune responses. Accordingly, the identification and structural characterization of glycolipids from the cell wall of bifidobacteria is the first step in correlating glycolipid structure with biological activity. Using whole cell MALDI as a screening tool, we herein present for the first time the identification and structural elucidation of the major polar lipids from Bifidobacterium longum subs. infantis. The lipids identified include an unprecedented plasmenyl cyclophosphatidic acid and a mixed acetal glycolipid, with the latter subsequently being isolated and found to suppress the innate immune response.
- Timmer, Mattie S. M.,Sauvageau, Janelle,Foster, Amy J.,Ryan, Jason,Lagutin, Kirill,Shaw, Odette,Harper, Jacquie L.,Sims, Ian M.,Stocker, Bridget L.
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p. 7332 - 7341
(2014/11/08)
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- METHODS FOR THE SYNTHESIS OF PLASMALOGENS AND PLASMALOGEN DERIVATIVES, AND THERAPEUTIC USES THEREOF
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A method for preparing plasmalogens and derivatives thereof represented by Formula B, wherein R1 and R2 are similar or different, derived from fatty acids; R3 is selected from hydrogen and small alkyl groups. The synthetic route involves production of novel cyclic plasmalogen precursors of Formula A and their conversion to plasmalogens and plasmalogen derivatives of Formula B. Also disclosed is the therapeutic use of plasmalogens and derivatives thereof as produced by the synthetic route of the present invention.
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Page/Page column 25-27
(2013/06/05)
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- Omega-functionalized fatty acids, alcohols, and ethers via olefin metathesis
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Methyl 17-hydroxy stearate was converted to methyl octadec-16-enoate using copper sulfate adsorbed on silica gel. This compound served as a useful substrate for the olefin metathesis reaction. As a result, several fatty acids with novel functional groups at the x-end were prepared: a glyceryl ether attached at the 18-carbon, an aromatic fatty acid from eugenol, and a ferrocenyl fatty acid. By employing the unsaturated fatty alcohol, other groups were introduced, namely the terminal fluoride, bromide, and iodide were prepared, as was a thiol derivative. The penultimate and omega olefins reported here should serve as building blocks that allow fatty acids to make a greater contribution to a range of emerging technological
- Zerkowski, Jonathan A.,Solaiman, Daniel K. Y.
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experimental part
p. 1325 - 1332
(2012/09/10)
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- Model studies toward a synthesis of asperaculin A: Exploration of iterative intramolecular Pauson-Khand reaction based strategies to access the dioxa[5.5.5.6]fenestrane framework
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A concise strategy, involving tandem intramolecular Pauson-Khand reactions (IPKRs) on a readily available ene-diyne precursor, to access the dioxa-fenestrane framework is delineated.
- Mehta, Goverdhan,Khan, Tabrez Babu
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scheme or table
p. 4558 - 4561
(2012/09/25)
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- Investigation of the catalytic activity of an electron-deficient vanadium(IV) tetraphenylporphyrin: A new, highly efficient and reusable catalyst for ring-opening of epoxides
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In this work, the catalytic activity of high-valent tetraphenylporphyrinatovanadium(IV) trifluoromethanesulfonate, [V IV(TPP)(OTf)2], in the nucleophilic ring-opening of epoxides is reported. This new V(IV) catalyst was used as an efficient catalyst for alcoholysis with primary (methanol, ethanol and n-propanol), secondary (iso-propanol) and tertiary alcohols (tert-butanol), hydrolysis and acetolysis of epoxides with acetic acid and also for the conversion of epoxides to 1,2-diacetates with acetic anhydride, conversion of epoxides to thiiranes with ammonium thiocyanate and thiourea, and for conversion of epoxides to acetonides with acetone. The catalyst was reused several times without loss of its activity.
- Taghavi, S. Abdolmanaf,Moghadam, Majid,Mohammadpoor-Baltork, Iraj,Tangestaninejad, Shahram,Mirkhani, Valiollah,Khosropour, Ahmad Reza,Ahmadi, Venus
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experimental part
p. 2244 - 2252
(2011/10/03)
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- Catalytic conversion of epoxides to 1,3-dioxolanes with phosphomolybdic acid (PMA) in solution and under solvent-free conditions
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The fast and efficient conversion of epoxides into 2,2-dimethyl-1,3- dioxolanes was studied with catalytic amounts of phosphomolybdic acid (PMA) (0.1-0.2 mol %) at room temperature in solution and under solvent-free conditions. The products were obtained in high to excellent yields within 1-2 min. Copyright Taylor & Francis Group, LLC.
- Zeynizadeh, Behzad,Sadighnia, Leila
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experimental part
p. 2274 - 2279
(2009/07/18)
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- Ring-opening reactions of epoxides catalyzed by molybdenum(VI) dichloride dioxide
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Transformation of epoxides to β-alkoxy alcohols, acetonides, and α-alkoxy ketones is achieved by using molybdenum(VI) dichloride dioxide (MoO2Cl2) as a catalyst. Alcohol, aldehyde, oxime, tosyl, and tert-butyldimethylsilyl functional groups are tolerated during the methanolysis and acetonidation of the functionalized epoxides. No polymerization product is observed with any of the epoxides. Direct conversion of epoxides devoid of sensitive functional groups into the corresponding α-methoxy ketone is achieved in a single step by using the MoO2Cl 2/Oxone system. Georg Thieme Verlag Stuttgart.
- Jeyakumar, Kandasamy,Chand, Dillip Kumar
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p. 807 - 819
(2008/09/21)
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- Novel organosilicon compound, organosilicon resin having diol, and processes for producing these
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[Problems] To provide a novel alkoxysilane having a diol protected, an organosilicon resin which has a diol and the composition of which can be easily regulated, and to processes for producing these. [Means for solving problems] The alkoxysilane is an organosilicon compound represented by the following formula (1). The organosilicon resin having a diol is one obtained by hydrolyzing-condensing this compound with a multifunctional alkoxysilane. (In the formula, each of R1, R2 and R3 is an alkyl group or an alkoxy group each having carbon number from 1 to 6. R4 is an alkylene group having carbon number from 2 to 6. Z is an alkylene group having carbon number from 1 to 3.) The alkoxysilane of the present invention can be produced by a hydrosilylation reaction of a compound represented by the following formula (4) and a silane compound R1R2R3SiH. (In the formula, Z is an alkylene group having carbon number from 1 to 3 and R5 has a carbon-carbon double bond at the terminal.) The organosilicon resin of the present invention can be produced by a hydrolysis-condensation of a mixture comprising the organosilicon compound represented by the formula (1) above and a molecular weight-controlling agent.
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Page/Page column 4
(2010/11/28)
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- Efficient and catalytic conversion of epoxides into 1,3-dioxolanes with LiBF4
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Lithium tetrafluoroborate catalysis the efficient conversion of epoxides with acetone to the corresponding 1,3-dioxolanes in excellent isolated yields. Copyright Taylor & Francis, Inc.
- Kazemi,Kiasat,Ebrahimi
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p. 1441 - 1445
(2007/10/03)
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- Rapid and efficient ring opening of epoxides catalyzed by a new electron deficient tin(IV) porphyrin
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The new electron deficient tin(IV) tetraphenylporphyrinato trifluoromethanesulfonate, [SnIV(tpp)(OTf)2], was used as an efficient catalyst for the alcoholysis, hydrolysis and acetolysis of epoxides. Conversion of epoxides to thiiranes and acetonides were also performed efficiently in the presence of this catalyst.
- Moghadam, Majid,Tangestaninejad, Shahram,Mirkhani, Valiollah,Shaibani, Reza
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p. 6105 - 6111
(2007/10/03)
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- Conversion of Epoxides to 1,3-Dioxolanes Catalyzed by Tin(II) Chloride
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Anhydrous tin(II) chloride is an efficient catalyst for the reaction of epoxides with acetone to prepare 2,2-dimethyl-1,3-dioxolanes (acetonides) in good to excellent yields. Mono-, di-, and trisubstituted epoxides participate equally well in this diastereospecific reaction. The use of single enantiomer epoxides under the reported conditions results in significant erosion of optical activity.
- Vyvyan, James R.,Meyer, Jennifer A.,Meyer, Korin D.
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p. 9144 - 9147
(2007/10/03)
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- Efficient conversion of epoxides to 1,3-dioxolanes catalyzed by bismuth(III) salts
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Epoxides react with acetone in the presence of catalytic amounts of bismuth(III) salts including BiCl3, Bi(TFA)3 and Bi(OTf)3 affording the corresponding 1,3-dioxolanes in excellent yields.
- Mohammadpoor-Baltork,Khosropour,Aliyan
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p. 3411 - 3416
(2007/10/03)
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- Conversion of epoxides into 1,3-dioxolanes catalysed by high oxidation state metalloporphyrins
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Tin(IV) tetraphenylporphyrin perchlorate, Sn(IV)(tpp)(ClO4)2, catalyses the efficient reaction of epoxides with acetone to give the corresponding 1,3-dioxolanes in good yields.
- Tangestaninejad,Habibi,Mirkhani,Moghadam
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p. 365 - 367
(2007/10/03)
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- Iron(III) trifluoroacetate as an efficient catalyst for solvolytic and nonsolvolytic nucleophilic ring opening of epoxides
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Iron(III) trifluoroacetate was used as an efficient and nonhygroscopic catalyst for the alcoholysis, hydrolysis, and acetolysis of epoxides. The addition of chloride, bromide, iodide, and nitrate ions to epoxides to produce the corresponding 2-halo and 2-nitratoalkanols and also the conversion of epoxides to acetonides and thiiranes were also performed efficiently in the presence of this catalyst.
- Iranpoor, Nasser,Adibi, Hadi
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p. 675 - 680
(2007/10/03)
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- Hydroxynitrile lyase catalyzed enantioselective HCN addition to O-protected α-hydroxyaldehydes
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Various O-protected glycol- and racemic lactaldehydes 3 and 6 as well as O-allyl protected racemic α-hydroxyaldehydes 7 (R1=Et, Pr, Bu) have been prepared to investigate and perform a stereoselective Kiliani-Fischer synthesis by hydroxynitrile lyase (HNL) catalyzed addition of HCN. From all protecting groups investigated the allyl moiety was most suitable. (R)-PaHNL from bitter almonds (Prunus amygdalus), yielding the (2S)-cyanohydrins 8-10, was found to be a more stereoselective catalyst than (S)-MeHNL from maniok (Manihot esculenta). While (R)-PaHNL led to enantiomeric excesses ≥93%, with (S)-MeHNL the (2R)-cyanohydrins 8-10 were obtained with enantiomeric excesses ≤78%.
- Roos, Juergen,Effenberger, Franz
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p. 2817 - 2828
(2007/10/03)
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- Efficient and Catalytic Conversion of Epoxides to 1,3-Dioxolanes with TiO(TFA)2 or TiCl3(OTf)
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TiO(TFA)2 or TiCl3(OTf) catalyses the efficient reaction of epoxides with acetone to give the corresponding 1,3-dioxolanes in excellent yields. The reaction of chiral styrene oxide was found to be highly stereospecific.
- Iranpoor,Zeynizadeh
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p. 466 - 467
(2007/10/03)
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- Sequential radical perfluoroalkylation - Nucleophilic cyclization. Synthesis of 2-perfluoroalkylidenemethyl and 2-perfluoroalkylmethyl-1,4-dioxanes from 1-O-allyl-1,2-diols
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The title compounds were synthesized by radical addition of perfluoroalkyl iodide to 1-O-allyl-1,2-diols and subsequent nucleophilic cyclization according to one of the following procedures. Basic treatment of the iodo F-alkyl adduct gave an olefinic compound which is stereoselectively cyclized with an excess of base into the corresponding 2-perfluoroalkylidenemethyl-1,4-dioxane through as S(N)' process. The direct cyclization of the adduct into 2-perfluoroalkylmethyl-1,4-dioxane was achieved by a new and simple method using molecular iodine or positive halogen reagents (DBH, NBS) for the activation of the carbon-iodine bond.
- Foulard, Gaelic,Brigaud, Thierry,Portella, Charles
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p. 6187 - 6200
(2007/10/03)
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- Dioxolane, diol and diacrylate silicon compounds and method for their preparation and use
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Dioxolane-substituted silicon compounds are prepared by a hydrosilylation reaction between a silicon hydride and an aliphatically unsaturated dioxolane compound. The dioxolane-substituted silicon compounds are thereafter converted to diol-substituted silicon compounds and then to diacrylate-substituted silicon compounds. The latter are useful in a curable coating composition for providing a substrate with an adhesive-releasing coating.
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