2-(E)-(取代苯亚甲基)环己酮的合成工艺研究

Synthesis of 2(E)-(Benzylidene)cyclohexanones

采用异香兰醛和环己酮为原料,以乙醇为溶剂,在哌啶催化作用下羟醛缩合合成了姜黄素类抗癌药物重要中间体2-(E)-(3-羟基-4-甲氧基苯亚甲基)环己酮,通过1H NMR对产品的结构进行确证。并对反应条件进行了优化,优化条件为n(异香兰醛)∶n(环己酮)=1∶3,催化剂为哌啶,且质量为环己酮质量的20%,常压下70℃混合反应,反应结束后通过干法柱层析纯化,2-(E)-(3-羟基-4-甲氧基苯亚甲基)环己酮的反应收率达60.5%。通过扩展实验可知同样适用于香兰醛、3,4,5-三甲氧基苯甲醛等芳醛。

（E）-2-（3-Hydroxy-4-methoxybenzylidene）cyclohexanone was synthesized from aldol condensation of 3-hydroxy-4-methoxybenzaldehyde and cyclohexanone using piperidine as catalyst in ethanol. Its structure was characterized by^1 H NMR. The experimental results showed that the optimal molar ratio of 3-hydroxy-4-methoxybenzaldehyde to cyclohexanone was 1：3; the optimal dosage of piperidine was 20% of cyclohexanone; the optimal temperature was 70℃. The target product was obtained in a yield of 60.5%. This method could also be applied in the preparation of Vanillin, 3,4,5-trimethoxybenzaldehyde and other aromatic benzaldehydes.