Dimmock J R, Smith P J, Noble L M, Pannekoek W J
J Pharm Sci. 1978 Nov;67(11):1536-9. doi: 10.1002/jps.2600671111.
A number of nuclear-substituted 1-phenyl-1-nonen-3-one oximes were synthesized. Reduction of several of these compounds with lithium aluminum hydride yielded the corresponding 1-phenyl-2,3-epiminononanes, shown by 100-MHz NMR spectroscopy to be the cis-geometrical isomers. When several ring-substituted 4-dimethylaminomethyl-1-phenyl-1-nonen-3-ones were treated with hydroxylamine hydrochloride under forcing conditions, the product isolated was the corresponding oxime. Reaction under mild conditions led only to the isolation of the Michael addition product of the oxime in low yield. Reduction of some nuclear-substituted 4-dimethylaminomethyl-1-phenyl-1-nonen-3-ones with sodium borohydride led to the formation of the corresponding allyl alcohols, and the products were shown by 1H- and 13C-NMR spectroscopy to be the threo-isomers or, alternatively, a mixture of erythro- and threo-isomers. Reaction of phosphoric acid with one of the substituted allyl alcohols led to a diolefin, shown by NMR spectroscopy to be a mixture of (E, E)- and (E, Z)-isomers in a ratio of 65:35.
合成了多种核取代的1-苯基-1-壬烯-3-酮肟。用氢化铝锂还原其中几种化合物，得到相应的1-苯基-2,3-环氧亚氨基壬烷，100兆赫核磁共振光谱表明其为顺式几何异构体。当几种环取代的4-二甲基氨基甲基-1-苯基-1-壬烯-3-酮在强制条件下用盐酸羟胺处理时，分离得到的产物是相应的肟。在温和条件下反应仅导致以低产率分离出肟的迈克尔加成产物。用硼氢化钠还原一些核取代的4-二甲基氨基甲基-1-苯基-1-壬烯-3-酮导致形成相应的烯丙醇，1H和13C核磁共振光谱表明产物为苏式异构体，或者是赤式和苏式异构体的混合物。磷酸与一种取代的烯丙醇反应生成一种二烯烃，核磁共振光谱表明其为（E,E）-和（E,Z）-异构体的混合物，比例为65:35。
