85353-80-6Relevant academic research and scientific papers
Friedel-Crafts alkylations on nanoscopic inorganic fluorides
Candu,Wuttke,Kemnitz,Coman,Parvulescu
experimental part, p. 169 - 174 (2011/10/05)
The catalytic potential of nanoscopic MFx (M = Mg, Al; x = 2, 3) has been investigated using batch Friedel-Crafts alkylation of aromatic compounds, including benzene, ethylbenzene, trimethylhydroquinone (TMHQ), and menadiol (MDL), with isophytol and benzyl alcohol. The conversion of isophytol was 100% in the reactions with trimethylhydroquinone (TMHQ), menadiol (MDL) and benzene while the highest selectivity in alkylated compounds was achieved with TMHQ (>99%). The different reaction rates of the alkylation reactions are due to the different nucleophylicities of the substrates, and therefore, due to their ability to delocalize the positive charge in the Wheland intermediate by inductive and resonance effects. The conversions of benzyl alcohol varied between 10 and 84% as a function of the catalyst nature and reaction conditions while the highest selectivity to monobenzyl derived compounds (25%) was achieved with ethylbenzene. The formation of high amounts of dibenzyl ether was also observed, indicating the presence of high amounts of Br?nsted acid sites in this type of catalysts.
Catalytic performance of nanoscopic, aluminium trifluoride-based catalysts in the synthesis of (all-rac)-α-tocopherol
Coman,Wuttke,Vimont,Daturi,Kemnitz
experimental part, p. 2517 - 2524 (2009/08/14)
A novel nanoscopic, partly hydroxylated aluminium fluoride was prepared in a sol-gel fluorination synthesis and characterised by IR probe molecules. It was shown that this material has, in contrast to high surface area aluminium fluoride (HSAlF3) which is one of the strongest Lewis acids, a low amount of strong Lewis acid sites combined with weak and medium strength Br?nsted sites. Both materials were tested in the synthesis of (all-rac)-α-tocopherol through the condensation of 2,3,6- trimethylhydroquinone (TMHQ) with isophytol (IP). The activity data indicate the partly hydroxylated aluminium fluoride to be a very efficient and highly selective catalyst for (all-rac)-α-tocopherol (>99.9%, for an IP conversion of 100%) whereas high surface area aluminium fluoride is a poor catalyst for this reaction.
PROCESS FOR THE MANUFACTURE OF ALKENYLATED HYDROXYLATED AROMATIC COMPOUNDS, OF CHROMAN COMPOUNDS AND OF THEIR ACYLATED DERIVATIVES
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Page/Page column 31-32, (2008/06/13)
The present invention relates to a novel process for the manufacture of alkenylated aro-matic compounds featuring at least one hydroxy group, their ring-closure reactions to chroman derivatives, as well as the acylation of the latter and the aromatic compounds featuring at least one hydroxy group themselves. The present invention relates especially to a process for the manufacture of tocol, tocopherols and their alkanoates such as α-tocopherol (TCP) and alkanoates (TCPA) thereof, preferably α-tocopheryl acetate (TCPAc). The processes of the present invention are characterized in that at least one step of the processes is carried out in the presence of an indium salt as the catalyst. Thus, an object of the present invention is the use of an indium salt as the catalyst in Friedel-Crafts alkylation reactions of aromatic compounds featuring at least one hydroxy group and ring-closure reactions of the latter to produce chroman-ring compounds in organic solvents. According to another aspect of the invention indium salts can be used as the catalyst in processes for the manufacture of tocyl alkanoates, tocopheryl alkanoates and alkanoates of aromatic compounds featuring at least one hydroxy group by reacting tocols, tocopherol and aromatic compounds featuring at least one hydroxy group, respectively, with an acylating agent. Suitable indium salts are indium(III) salts, especially indium trichloride, indium tribromide or indium triiodide, indium(III) triflate, indium(III) bis(trifluoromethanesulfonamide) and indium(III) acetate. In preferred embodiments of the invention the processes are carried out at a pressure of at least 0.96 bar, whereby the acylation can be carried out at an absolute pressure of at least 0.02 bar.
Tocopherol, tocotrienol, other chromane, and their side chain deriv. and method for using the same
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Page/Page column 41, (2008/06/13)
The present invention provides an antiproliferative compound having the structural formula wherein X is oxygen, nitrogen or sulfur; Y is selected from the group consisting of oxygen, nitrogen and sulfur wherein when Y is oxygen or nitrogen, n is 1 and when Y is sulfur, n is 0. Also provided is a method for inducing apoptosis in a cell comprising administering a composition comprising a compound having said structural formula.
Tocopherols, tocotrienols, other chroman and side chain derivatives and uses thereof
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Page column Sheet 8; 36, (2008/06/13)
The present invention provides an antiproliferative compound having a structural formula where X and Y independently are oxygen, nitrogen o r sulfur; R1 is alkyl, alkenyl, alkynyl, aryl, heteroaryl, carboxylic acid, carboxylate, carboxamide, ester, thioamide, thiolacid, thiolester, saccharide, alkoxy-linked saccharide, amine, sulfonate, sulfate, phosphate, alcohol, ethers or nitriles; R2 and R3 are hydrogen or R4; R4 is methyl, benzyl carboxylic acid, benzyl carboxylate, benzyl carboxamide, benzylester, saccharide or amine; and R5 is alkenyl; where when Y is nitrogen, said nitrogen is substituted with R6, wherein R6 is hydrogen or methyl. Also provided are methods for treating a cell proliferative disease and for inducing apoptosis in a cell comprising administering this compound is also provided.
PRODUCTION OF 2-ALKENYL-3,5,6-TRIMETHYL-1,4-BENZOQUINONES AND THEIR WATER-SOLUBLE FORMS
Byzova, V. N.,Zakharova, E. I.,Zhukova, E. E.,Sarycheva, I. K.,Evstigneeva, R. P.
, p. 2135 - 2140 (2007/10/02)
A method is described for the synthesis of 3,5,6-trimethyl-1,4-benzoquinones containing isoprenoid substituents with hydrocarbon chain lengths between C5 and C20 at position 2 by the condensation of 2,3,5-trimethylhydroquinone or its
