68279-46-9Relevant academic research and scientific papers
Thermodynamic, spectroscopic, and density functional theory studies of allyl aryl and prop-1-enyl aryl ethers. Part 1. Thermodynamic data of isomerization
Taskinen, Esko
, p. 1824 - 1834 (2007/10/03)
A chemical equilibration study of the relative thermodynamic stabilities of seventy isomeric allyl aryl ethers (a) and (Z)-prop-1-enyl aryl ethers (b) in DMSO solution has been carried out. From the variation of the equilibrium constant with temperature the Gibbs energies, enthalpies, and entropies of isomerization at 298.15 K have been evaluated. Because of their low enthalpies, the (Z)-prop-1-enyl aryl ethers are strongly favored at equilibrium, the Gibbs energies of the a→b isomerization ranging from -12 to -23 kJ mol-1. The entropy contribution is negligible in most reactions, but occasionally small positive values less than +10 J K-1 mol-1 of the entropy of isomerization are found. The equilibration studies were also extended to involve two pairs of related isomeric ethers with a Me substituent on C(2) of the olefinic bond. The Me substituent was found to increase the relative thermodynamic stability of the allylic ethers by ca. 3.4 kJ mol-1.
Synthesis of methyl 2,3-dihydro-2-benzofurancarboxylates from o-allylphenols via 2-(phenylthiomethyl)-2,3-dihydrobenzofurans
Yodo, Mitsuaki,Harada, Hiroshi
, p. 2361 - 2368 (2007/10/02)
A method for synthesizing methyl 2,3-dihydro-2-benzofurancarboxylates rom o-allylphenols is described.The reaction of 6allyl-2,3-dichlorophenol (3) with benzenesulfenyl chloride (PhSCl) in acetonitrile gave a mixture of PhSCl -adducts, which was heated in aqueous acetonitrile then with sodium bicarbonate to obtain 6,7-dichloro-2-(phenylmethyl)-2,3-dihydrobenzofuran (6). α-Dichlorination of the phenylthiomethyl group of 6 and subsequent methanolysis gave the methyl ester 5 in high yield.The generality of this synthetic method was examined by the conversion of o-allylphenols 11 having various substituents on the benzene ring into the corresponding methyl ester 23.Cyclization of 11 to sulfides 12 could be achived similerly to the case of 3.However, in the subsequent conversions of 12 to 23, selective α-dichlorination followed by methanolysis could be achived only with 12 substituted with an electron-withdrawing group such as a chloro or nitro group.Keywords - oallylphenils; methyl 2,3-dihydro-2-benzofurancarboxylate; 2-(phenylthiomethyl)-2,3-dihydrobenzofuran; benzenesulfenyl chloride; α-chlorination; methanolysis.
α-Adrenoreceptor Reagents. 2. Effects of Modification of the 1,4-Benzodioxan Ring System on α-Adrenoreceptor Activity
Chapleo, Christopher B.,Myers, Peter L.,Butler, Richard C. M.,Davis, John A.,Doxey, John C.,et al.
, p. 570 - 576 (2007/10/02)
Modification of the 1,4-benzodioxan ring present in RX 781094 (1) has not previously been considered.This paper describes a number of analogues of this ring system, including compounds in which one of the oxygen atoms has been replaced by a methylene group and also those in which the ring size has been changed to give, for example, furan and thiophene derivatives.The dihydroxybenzofuranylimidazoline compound 7 is the only analogue possesing presynaptic antagonist potency and selectivity comparable to that of 1.In view of this result, a number of derivatives was prepared to determine the structure-activity relationships within this series.Many derivatives, as well as the parent compound 7, were found to possess presynaptic α2-adrenoreceptor antagonist and postsynaptic α1-adrenoreceptor partial agonist properties.Two of the selective presynaptic antagonists,13 and 14, possess greater potency and selectivity than that possessed by 1.The 5-chloro derivative 25 is twice as potent as 1 after oral administration but only about half as potent when given intravenously.
(Acylaryloxy)acetic Acid Diuretics. 3. 2,3-Dihydro-5-acyl-2-benzofurancarboxylic Acids, a New Class of Uricosuric Diuretics
Hoffman, William F.,Woltersdorf, Otto W.,Novello, Frederick C.,Cragoe, Edward J,Spinger, James P.,et al.
, p. 865 - 873 (2007/10/02)
The discovery that dihydroethacrynic acid and other (4-acylphenoxy)acetic acids possessed modest but significant uricosuric and diuretic activity prompted our investigation of the related 2,3-dihydro-5-acyl-2-benzofurancarboxylic acids.Synthetic routes to
Use of cyclic esters to prepare 2,3-dichloro-4-(2-thenoyl)phenoxyacetic acid
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, (2008/06/13)
A new process and intermediates for preparing 2,3-dichloro-4-(2-thenoyl)phenoxyacetic acid (ticrynafen, a diuretic agent) using as a key reaction a Friedel-Crafts acylation of an esterified 3-(2,3-dichlorophenoxy)-1,2-propanediol using a thenoyl halide.
