aber писал(а):вероятно, ошибка в странице: 6511 - это слишком много
скорее стр. 654-655 по данным SF "Структура и синтез алкалоида анаферина"
Structure and synthesis of the alkaloid anaferine. Rother, A.; Bobbitt, J. M.; Schwarting, A. E. Univ. of Connecticut, Storrs, Chem. Ind. (London, U. K.) (1962), 654-5. CODEN:CHINAG ISSN:0009-3068. Journal written in Unavailable. CAN 57:62953 AN 1962:462953 CAPLUS
ABSTRACT Anaferine (I) was isolated as a dihydrochloride, m. 222.523.5°, [α]22D 0°, from an alc. ext. of the root of Withania somnifera by ion-exchange chromatography and countercurrent distribution. I is hydroscopic, b0.01, 55°, and discolors in air, characterized as a dipicrate, m. 184-5° (decompn.) and distyphnate, m. 229-31°. I has ν 3270 cm.-1 (N-H) and 1710 cm.-1 (ketone C:O). It is a disecondary amine and forms an N,N'-diacetyl deriv., b0.02 120°. The diacetyl compd. shows no peaks at 3270 cm.-1 but does show an amide carbonyl at 1640 cm.-1 as well as the unchanged ketone carbonyl at 1710 cm.-1 A peak at 84 in the mass spectrum corresponds to the piperidine fragment found by the cleavage of I. Nuclear magnetic resonance spectrum show peaks at 7.083 τ, 7.65 τ, and 8.55 τ. From the data and biogenetic considerations I was assigned the structure of bis(2-piperidyhnethyl) ketone which was confirmed by synthesis. Thus ethyl chloroformate was condensed with 2 moles of 2-picolyllithium to give bis(2-pyridylmethyl) ketone (II) in 5% yield after chromatography over silica gel, b0.01 50°; dipicrate m. 193.5-94.,5°, ν 1710 cm.-1 Hydrogenation of II in HOAc over PtO2, gave 1,3-di(2-pyridyl)-2-pro-panol (III). The major spot on thin-layer chromatography (silica gel-alumina) of III was identified with one found by hydrogenation of I. The isomer mixt. was oxidized with chromic acid to yield I. I is optically inactive but whether it is the meso or the d1 form of I is not known.