摘要
螺双二氢茚二酚(SPINOL)与N-溴代丁二酰亚胺经溴代反应制得6,6'-二溴-螺双二氢茚二酚(1);1与叔丁基二甲基硅基三氟甲磺酸(TBSOTf)经醚化反应得6,6'-二溴-7-羟基-7'-叔丁基二甲硅氧基-1,1'-螺二氢茚(2);SPINOL经羟基保护后与碘甲烷经双甲基化反应制得6,6'-二甲基-7,7'-双(1-甲氧甲氧基)-1,1'-螺二氢茚(4);4经脱保护后再与TBSOTf经醚化反应合成了6,6'-二甲基-7-羟基-7'-叔丁基二甲硅氧基-1,1'-螺二氢茚(6)。2和6为新化合物,其结构经1H NMR,13C NMR和HR-ESI-MS表征。
6,6＇-Dibromo-7＇-[（ tert-butyldimethylsilyl） oxy]-2,2＇,3,3＇-tetrahydro-1,1＇-spirobi[inden]-7-ol（ 2） was synthesized by etherification of TBSOTf with 6,6＇-dibromo spirobiindane（ 1）,which was obtained by bromination of SPINOL with NBS. 6,6＇-Dimethyl-1,1＇-spirobiindane-7,7＇-bis（ 1-methoxymethoxy）（ 4） was obtained by hydroxyl protection and methylation from SPINOL. 7＇-[（ Tert-butyldimethylsilyl） oxy]-6,6＇-dimethyl-2,2＇,3,3＇-tetrahydro-1,1＇-spirobi[inden]-7-ol（ 6）was synthesized by deprotection and single-protection with TBSOTf from 4. 2 and 6 were novel compounds and the structures were characterized by1 H NMR,13 C NMR and HR-ESI-MS.
出处
《合成化学》
CAS
CSCD
2015年第10期945-947,951,共4页
Chinese Journal of Synthetic Chemistry
基金
国家自然科学基金资助项目(21102175
21372259)
关键词
螺双二氢茚二酚
溴代
甲基化
羟基保护
合成
1,1＇-spirobiindane-7,7＇-diol
bromination
methylation
hydroxyl protection
synthesis
