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以取代苄胺为原料,经过Michael加成、Dieckmann缩合、水解脱羧、羟醛缩合等反应,合成一个未见文献报道的化合物:N-(4-甲基苄基)-3,5-双(4-氯苄叉基)-4-哌啶酮.目标化合物的结构经元素分析、核磁共振氢谱(1H NMR)、红外光谱(IR)、质谱(EI-MS)及单晶X-射线衍射测定确定.该单晶属于单斜晶系,空间群为P2(1),a=17.1226(16),b=6.28396(6),c=21.468(2),α=90°,β=99.753°,γ=90°,V=2276.5(4)3,Z=4,Dc=1.308 g/cm3=0.304 mm-1,Mr=448.36,F(000)=936,S=1.019,R=0.0585以及wR=0.1456.目标化合物的结构是非平面的,哌啶环呈沙发构象.化合物中的碳碳双键都是E式构的.在晶体结构中没有分子内和分子间氢键存在.生物活性测试结果表明:目标化合物对白血病K562细胞系的增殖有明显的抑制作用,具有潜在的抗癌活性.
The substituted benzylamine was used as a starting material to synthesize a compound which has not been reported in the literature after Michael addition, Dieckmann condensation, hydrolysis decarboxylation, aldol condensation, etc. N- (4-methylbenzyl) -3,5-bis 4-chlorobenzylidene) -4-piperidinone.The structure of target compound was confirmed by elemental analysis, 1 H NMR, IR, EI-MS and single crystal X-ray diffraction The single crystal belongs to the monoclinic system with space group P2 (1), a = 17.1226 (16), b = 6.28396 (6), c = 21.468 (2), α = 90 ° and β = 99.753 ° , γ = 90 °, V = 2276.5 (4) 3, Z = 4, Dc = 1.308 g / cm3 = 0.304 mm-1, Mr = 448.36, F (000) = 936, S = 1.019, R = 0.0585 and wR = 0.1456.The structure of the target compound is non-planar, and the piperidine ring is in the conformation of the sofa.The carbon-carbon double bonds in the compounds are both E-type structures, and there is no intramolecular and intermolecular hydrogen bond present in the crystal structure. The results showed that the target compound could obviously inhibit the proliferation of leukemia K562 cell line and had potential anticancer activity.