(S)-2'-甲氧基-2-丙烯酰基-1,1'-联萘的合成

Synthesis of (S)-2'-Methyloxy-2-acrylyl-1,1'-binaphthyl

以1-羟基-2-萘甲酸与2-甲氧基萘为起始原料通过多步反应合成了标题化合物。首先将1-羟基-2-萘甲酸转化为1-(-)-薄荷氧基-2-萘甲酸-(-)-薄荷酯,再将2-甲氧基萘转化为1-溴-2-甲氧基萘,1-溴-2-甲氧基萘的格氏试剂与酯反应得到(S)-2'-甲氧基-1,1'-联萘-2-甲酸-(-)-薄荷酯。该薄荷酯再经还原反应、氧化反应、加成反应、氧化反应得到标题化合物。对各步反应的实验条件进行了适当改进,找到了较好的合成条件,并用1HNMR和13CNMR对各步产物进行了表征。

（ S ） -2′-Methyloxy-2-acrylyl-1, 1′-binaphthyl was synthesized from 1-hydroxy-2-naphthoic acid and methyl 2-naphthyl ether by multi steps. Firstly, methyl 1-methoxy-2- naphthoate was synthetized from 1-hydroxy-2-naphthoic acid, and then methyl 2-naphthyl ether was converted to 1-bromo-2- metho：tynaphthalene. The Grignard reagent of 1-bromo-2-me- thoxynaphthalene was treated with （ - ）-menthyl 1-（ - ） menthyloxy-2-naphthoate to form（ - ）-menthyl（S）-2′-methy- loxy-1, 1′-binaphthalene-2-earboxylate. The target compound was synthesized from （ - ）-menthyl 1-（ - ） menthyloxy-2- naphthoate via reduction, oxidation, addition, oxidation. The suitable reaction conditions were obtained and structures of the products were identified by I HNMR and 13CNMR.