期刊论文

Synthesis of(S)-6-vinyl-2,2’-methylenedioxy-1,1’-binaphthyl

中文

湖南城市学院学报(自然科学版)

1672-7304

2018

27

1

75-78

10.3969/j.issn.1672-7304.2018.01.0017

14A025:湖南省教育厅科学研究项目

本校为第一机构

以（S）-联萘酚为起始原料通过多步反应合成了（S）-6-乙烯基-2,2’-甲叉二氧基-1,1’-联萘﹒首先将（S）-联萘酚通过2步合成了（S）-6-溴-2-特戊酰氧基-2’-羟基-1,1’-联萘;再脱去特戊酰基得到了（S）-6-溴-2,2’-二羟基-1,1’-联萘;然后羟基醚化得到（S）-6-溴-2,2’-甲叉二氧基-1,1’-联萘;接下来与DMF反应得（S）-6-甲酰基-2,2’-甲叉二氧基-1,1’-联萘;最后通过维蒂希反应得标题化合物﹒研究优化了各步反应的实验条件,获得了较好的合成方案,通过1H NMR和13C NMR对各步产物进行了表征﹒

(S)-6-vinyl-2,2'-methylenedioxy-1,1'-binaphthyl was synthesized from (S)-2,2'-dihydroxy-1,1'-binaphthyl by multi steps. Firstly, (S)-6-bromo-2-hydroxy-2'-pivaloyloxy-1,1'-binaphthyl was synthesized from (S)-2,2'-hydroxy-1,1'-binaphthyl by two steps, and then (S)-6-bromo-2,2'-methylenedioxy-1,1'-binaphthyl was obtained by the reaction of hydrolysis and etherification. The lithium reagent of (S)-6-bromo-2,2'-methylenedioxy-1,1'-binaphthyl was treated with DMF to form (S)-6-formyl-2,2'-methylenedioxy-1,1'-binaphthyl. The target compound was synthesized from (S)-6-formyl-2,2'-methylenedioxy-1,1'-b...