This investigation was undertaken with the aim of synthesizing compounds from which, because of their structural similarity to oestrone (I), some oestrogenic activity might be expected.2 2-Hydroxy-9,10-dihydrophenanthrene (II) appeared
The distribution functions possess maxima characteristics similar to those previously discussed for "r = 1" polymers. In fact, the same equations may be used for locating the xmax. value for * by replacing p with r!lp. Exact equations for Mw and Mz, corresponding to equations ( 13) and ( 14), are cumbersome; for all practical purposes it is permissible merely to replace p with r''lp in ( 13) and ( 14), respectively. It follows that here also the ratio of M": Mw: z approaches 1:2:3 for high molecular weights. Thus, sedimentation equilibrium measurements in the ultracentrifuge would not distinguish the two types of polymers.
Derivatives of 1,3-Di-(^-hydroxyphenyl) -propane 1579 4-hydroxyphenyl)-ethane, in common with hexestrol, are geometrically related to estradiol but, in contrast, have no estrogenic activity.2. The amino analog of hexestrol, 3,4-bis-(£aminophenyl)-hexane, is inactive.3. Replacement of the ^-hydroxyphenyl groups of hexestrol with 3,4-dihydroxyphenyl or p-hydroxybenzyl results in decreased estrogenic activity.Pearl River, N. Y.
Dialkyl Derivatives of 1 ,3-Di-(P-hydroxyphenyl) -propane 1475 ml. of dry ether. A crystal of iodine was added, followed by 1 ml. of ethyl bromide. As soon as the reaction had started, the stirrer was turned on, a slow stream of dry nitrogen was passed through the flask and 60 g. (0.4 mole) of l-diethylamino-3-chloropropane, dissolved in 100 ml. of dry ether, was added over a period of ten minutes. Another ml. of ethyl bromide was added, the flask was heated in a water-bath vept at 45-50°for five minutes and then 27.2 g. (0.2 mole) of anisaldehyde, dissolved in 160 ml. of dry ether,1? was added over a period of ninety minutes. The stirring, heating and nitrogen flow were continued during the addition and for twelve hours after the addition was complete. A white precipitate formed.9 10 After standing overnight the reaction mixture was hydrolyzed by a solution of 75 g. of ammonium chloride in 200 ml. of water.
ammonia was allowed to remain in a thermostat at 30" for three days. Twenty-five cc. aliquots of this solution were refluxed for seven hours with 15 cc. of concentrated hydrochloric acid, after which the solution was codled in an ice-bath and made alkaline by the addition of solid sodium hydroxide. The alkaline solution was extracted with two 50-cc. and one 25-cc. portion of ether. The ether extracts were washed with 30 cc. of water and extracted with one 60-cc. and two 20-cc. portions of a solution of 15 cc. of concentrated hydrochloric acid in 85 cc. of water. The acid solution was boiled to expel ether. To the cooled acid solution was added 12 cc. of 10% potassium bromide solution, after which it was titrated with approximately 0.15 N standard potassium bromate solution. The end-point was determined by spotting on starch-potassium iodide paper. One cubic centimeter of 0.1 N potassium bromate is equivalent to 1.551 mg. of aniline. This method gave results reproducible to within 0.8%.The yield of amine from benzoyl p-methoxybenzhydroxamate, benzoyl p-methylbenzhydroxamate, mnitrobenzoyl p-methylbenzhydroxamate, m-nitrobenzoyl P-methoxybenzhydroxamate, benzoyl m-methylbenzhydroxamate, benzoyl m-methoxybenzhydroxamate and mfluorobenzoyl benzhydroxamate was determined by dissolving 1 to 2 g. of the potassium salt of the dihydroxamic acid in the amount of 0.1 N ammonia calculated to make a 0.026 molar solution and allowing the salt to decompose in the thermostat at 3 0 ' . The solution was then made acid with 20 cc. of concentrated hydrochloric acid and refluxed for seven hours. The solution was concentrated to about 50 cc. by distillation, cooled in an ice-bath and made alkaline by addition of solid potassium hydroxide. The alkaline solution was extracted with two 50-cc. and one 25-cc. portion of ether and the combined ether extracts washed with 30 cc. of water. The ether solution was extracted 6 t h two 25-cc. portions of 3 N hydrochloric acid. The acid solutions were combined in a weighed beaker, evaporated to dryness on a water-bath and finally dried in a desiccator over Drierite until their sveight did not change after a day in the desiccator. The yield of amine was calculated from the weight of amine hydrochloride obtained in this way. This method gave results that were reproducible to within 2%.1. The rates of decomposition of the potassium salts of a series of meta and para substituted dibenzhydroxamic acids, R-&-A-+&-R~, have been determined at 30'. A qualitative inverse relationship has been found between the ionization constants of benzoic acids corresponding to R and the rates of decomposition of dihydroxamic acid salts in which the effect of substituents in R alone was considered. A quantitative direct relationship has been found between the ionization constants of benzoic acids corresponding to R' and the rates of decomposition of dihydroxamic acid salts in which the effect of substituents in R' alone was being considered.2. These results support the hypothesis that the rate determining step in a Hofma...
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