Rotenone. I. Reduction Products of Rotenone

Abstract

CiüHnON-HCl 15.58 15.05 15.37 " Chlorine and nitrogen determinations were unsatisfactory. Summary 1. Acylanilines and acyltoluidines have anesthetic properties, particularly their hydrochlorides, if there is at least a butyrophenone skeleton.2. Data concerning eight such compounds are given.3. Six of the eight amines are new and are described together with their intermediates and, in some cases, their derivatives.

Rotenone photodecomposition

“…[The Roman numerals given below, after the names of some compounds, indicate that they are not structurally defined in Figure 1; the numerals given refer to the respective structures assigned to the compounds by Crombie (1963).] Rotenone was decomposed in ethanolic potassium hydroxide solution in the presence of zinc powder (Hamada and Chubachi, 1969;LaForge and Smith, 1929) to give derritol (XLII) [mp 162-3°C, reported as 164°C; mass spectra (ms) fragments at 370 (M+), 203,194,175,167,166,147,137] and rotenol (LIX-LX) (mp 118-9°C, reported as 120°C). Treatment of rotenone with 5% ethanolic potassium hydroxide yielded tubaic acid [mp 127-8 °C, reported as 129 °C by Haller and LaForge (1930); ms fragments at 220 (M+), 203,202,176,174,146] [methyl ester: mp 51-2°C, reported as 48°C by Butenandt (1928); ms fragments at 234 (M+), 203, 202, 175, 174, 146; infrared (ir) spectral peaks at 3200-3100 (hydrogen-bonded OH), 1665 (C=0), 1625, 1600, and 1490 cm"1 (phenyl)].…”

A 4-[6,7-dimethoxybenzopyranyl]5-[4-hydroxy-2-isopropyl benzofuranyl]ketone obtained by catalytic hydrogenation of rotenone

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UDC 547.972 Rotenone was hydrogenated by H 2 /chloroplatinic acid in absolute ethanol, yielding three products: dihydrorotenone (1) and dihydrodehydrorotenone (2), which have already been identified [1,2], and 4-[6,7-dimethoxybenzopyranyl]5-[4-hydroxy-2-isopropyl benzofuranyl]ketone (3) for which to our knowledge no analytical data have been published yet, although similar structures have been described elsewhere [3,4], which mentioned that the compound was obtained as a result of the opening of the C-ring in basic medium [5][6][7][8]. In our case the mechanism of formation of 3 was not clearly manifested as we did not operate in basic conditions; we then hypothesized that our catalyst might have contained a basic impurity.

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Synthesis of 14C‐labeled benzofurano[2,3‐b] benzopyran‐6‐one and its 4‐hydroxycoumarin derivative

“…Isorotenone(Ib),which has the biological activity a s rotenone(Ia) (8), was heated under reflux in ethanolic alkaline solution in the presence of zinc dust to give the deoxybenzoin IIb, known as isoderritol (9). In this process, however, a ten-fold excess of ethyl formate are usually employed, resulting in dilution of specific activity of the product obtained.…”