Benzenesulfonic acid esters

A number of substituted benzenesulfonic acid esters and p-chlorophenoxy-isobutyric acid esters produced hypolipidemic activity.35 Among a series of p-alkoxybenzoic acids, enhanced hypotriglyceridemic and hypocholesterol-emic activity was observed with oximino- (14) and chloro- (15) substituents.98 Hypocholesterolemia was observed after the administration of 16 to rats.97 Tetronic 701, a polymeric surfactant, also lowered serum cholesterol the tetrabenzoate of Tetronic 701 is of particular interest, since it produced comparatively less growth depression.98 Two linoleamide derivatives, (-)N-fa-phenyl-B-(p-tolyl)ethylllinoleamide (PTLA) and N-(a-methyl-benzoyl)linoleamide, suppressed serum and liver cholesterol levels in rats and inhibited cholesterol absorption b interfering with the hydrolysis of cholesteryl esters in the intestine.99 101... 

Biphenyl-2,2 -diamine and ring-substituted biphenyl-2,2 -diamines are transformed into dibenzo[rf,/][l JJdiazepines 1 in various ways by reaction with ortho esters (Method A),169 with hydrochlorides of imido acid esters (Method B)170 or with the benzenesulfonates of pro-tonated nitriles (Method C).171 Selected examples are given. 

Oae found that for both base- and acid-catalyzed hydrolysis of phenyl benzenesul-fonate, there was no incorporation of 0 from solvent into the sulfonate ester after partial hydrolysis. This was interpreted as ruling out a stepwise mechanism, but in fact it could be stepwise with slow pseudorotation. In fact this nonexchange can be explained by Westheimer s rules for pseudorotation, assuming the same rules apply to pentacoordinate sulfur. For the acid-catalyzed reaction, the likely intermediate would be 8 for which pseudorotation would be disfavored because it would put a carbon at an apical position. Further protonation to the cationic intermediate is unlikely even in lOM HCl (the medium for Oae s experiments) because of the high acidity of this species a Branch and Calvin calculation (See Appendix), supplemented by allowance for the effect of the phenyl groups (taken as the difference in between sulfuric acid and benzenesulfonic acid ), leads to a pA, of -7 for the first pisTa of this cation about -2 for the second p/sTa. and about 3 for the third Thus, protonation by aqueous HCl to give the neutral intermediate is likely but further protonation to give cation 9 would be very unlikely. 

R)-(-)-Methyl 3-hydroxybutanoate Butyric acid, 3-hydroxy-, methyl ester, D-(-)- (8) Butanoic acid, 3-hydroxy-, methyl ester, (R)- (9) (3976-69-0) p-Toluenesulfonic acid monohydrate (8) Benzenesulfonic acid, 4-methyl-, monohydrate (9) (6192-52-5)... 

It has been found that triamcinolone [101] and the 21-phosphate esters [102] do not under go the Porter-Silber reaction. It was also shown that an increased sensitivity for this procedure can be obtained using the p-hydrazino-benzenesulfonic acid-phosphoric acid reagent [103],... 

A second component in this mutagenic subfraction was shown to have an empirical formula of C8H10O2S. The compound was tentatively identified as the ethyl ester of benzenesulfonic acid. This structural assignment was made from exact mass analysis and interpretation of the following ions a molecular ion at 170.0400 mass units a characteristic... 

Formation of quinuclidine-3-carboxylic acid derivatives (68) from these reactions was conclusive proof of saponification of the ethoxy-carbonyl group at position 2 of the diester (61). A similar reaction takes place with diethyl quinuclidine-2,3-dicarboxylate.100 This is in agreement with the known principle of easier saponification of a- than j8-amino acid esters. Some 3-(j8-acyloxyethyl)-2-diethylaminomethyl-quinuclidines (69, 70)123 on distillation at atmospheric pressure cyclize with loss of ester and formation of a new tricyclic system, quinuclidino[2,3-c]piperidine (72). The same reaction takes place by heating the corresponding amino alcohol (71) with phthalic anhydride in the presence of benzenesulfonic acid.123... 

Methylation of 7-amino-l,2,3-triazolo[4,5-d]pyrimidine (8-azaadenine) (140) with dimethyl sulfate afforded the N-3 and N-9 methylated isomers 141 and 142, respectively, which upon further methylation with methyl iodide or benzenesulfonic acid methyl ester gave 3,7- and l,9-dimethyl-8-azaadeninium salts 144 and 145, respectively. Thermal decomposition of the dimethyl derivatives led to a transmethylation to give 6-methylamino-9-methyl-8-azapurine (143), whose methylation afforded 1- and 7-methyl-6-methylamino-9-methyl-8-azapurinium salts 146 and 147 (80ZOR2204) (Scheme 28). 

Furfural (18) was oxidized to give the butenolide 19, which on Michael condensation with diethyl ethylmalonate afforded lactone 20. Hydrolysis of 20 yielded the dilactone 21. This was treated with ethanol in the presence of sulfuric acid. The isomer mixture obtained was separated by preparative thin-layer chromatography, yielding 4-ethoxy-3-ethoxycarbonylmethyl-2-ethyl-4-butanolide (22). Elimination of ethanol, with the aid of p-amino-benzenesulfonic acid, gave 2-(3//)-furanone 23 the 2-(5//)-furanone isomer 24 was obtained with the aid of orthophosphoric acid. Both isomeric esters gave the acid 25 after hydrolysis, which on catalytic hydrogenation afforded m-3-carboxymethyl-2-ethyl-4-butanolide 26, identical to homopilopic acid. This synthesis of homopilopic acid differs from earlier syntheses because the less stable cw-2,3-disubstituted butanolide (26) is formed in the last step. 

BENZENESULFONATE 2,4-DICHLOROPHENYL BENZENESULPHONATE 2,4-DICHLOROPHENYL ESTER of BENZENESULFONIC ACID 2,4-DICHLOROPHENYL ESTER BENZENESULPHONIC ACID DPBS EM 923 GENITE GENITOL... 

Dodecyl benzenesulfonates Polyoxyethylene fatty acid esters... 

SOOsP2C4,H44, Osmium, carbonyl(5-thioxo-1,3-pentadiene-1,5-diyl-C, C, 5)bis(tri-phenylphosphine)-, 26 188 SO2C7H, Benzenesulfonic acid, 4-methyl-, rhodium complex, 27 292 S04PC,H,2. 2-Butenedioic acid, 2-(dimeth-ylphosphinothioyl)-, dimethyl ester, manganese complex, 26 163 SO C H , Thiophenetetracarboxylic add. tctramethyl ester, 26 166... 

Benzenesulfonic acid, 882 Benzenesulfonic anhydride, 46 Benzenesnlfonyl chloride, 46-48, 867, 1280 Benzenesulfonyl esters, 47 Benzenesnlfonyl isocyanate, 48 N-Benzenesulfonyl-1,4-naphthoquinone-4-imine, 559... 

Attempts have been made to Increase the specificity of sulfonyl compounds with respect to degree of inhibition of trypsin, plasmin, thrombin, kallikrein and urokinase. Nltrophenyl esters of benzenesulfonic acid and... 

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