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本文报导炔二醇的合成与环化,及环化产物的结构问题。将多聚甲醛三聚乙醛及环氧乙烷与乙炔基环已醇(Ⅰ)及格氏试剂交换而得的镁衍生物反应,分别得3-(1＇-羟代环已基)丙炔-2-醇-1(Ⅱ),4-(1＇-羟代环已基)丁炔-3-醇-2(Ⅲ)及4-(1＇-羟代环已基)丁炔-3-醇-1(Ⅳ)。 用甲酸磷酸混合酸处理,Ⅱ,即实现环化而生成4,5,6,9-四氢茚满酮(Ⅵ);而相似的处理却将Ⅲ及Ⅳ都各自环化为同一物,即3-甲基-4,5,6,9-四氢茚满酮(Ⅶ)。这样,就提供了一种新的合成四氢茚满酮的路线 在光谱和化学论据的基础上,对环化产物中有关双键的准确位置的细微结构问题,进行了讨论。
This paper reports the synthesis and cyclization of acetylenic diols and their structural problems. The reaction of paraformaldehyde and its derivatives with magnesium oxide obtained by the exchange of ethylene oxide with ethynylcyclohexanol (I) and Grignard reagents gives 3- (1’-hydroxycyclohexyl) propyne (II), 4- (1’-hydroxycyclohexyl) butyn-3-ol-2 (III) and 4- (1’-hydroxycyclohexyl) - alcohol - 1 (Ⅳ). With formic acid phosphoric acid mixed treatment, Ⅱ, that is, cyclization to generate 4,5,6,9-tetrahydroindanone (Ⅵ); and similar treatment, but Ⅲ and Ⅳ are each cyclized to the same thing, namely 3-methyl-4,5,6,9-tetrahydroindanone (VII). Thus, a new synthetic tetrahydrindanone route was discussed based on spectroscopic and chemical evidence of the fine structure of the cyclized product at the exact position of the double bond.