5,5-Dimethoxy-bicyclo[2.2.2]oct-2-en-1-ol | 868673-77-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,5-Dimethoxy-bicyclo[2.2.2]oct-2-en-1-ol
• CAS: 868673-77-2
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: CQFVTEDWUDOKIU-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  5,5-Dimethoxy-bicyclo[2.2.2]oct-2-en-1-ol 、 溴甲苯 在 四丁基碘化铵 、 sodium hydride 、 盐酸 、 水 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 20.0h， 以93%的产率得到4-benzyloxy-bicyclo[2.2.2]oct-5-en-2-one
  参考文献：
  名称：

  Asymmetric baker’s yeast reductions of bridgehead-substituted bicyclo[2.2.2]octane-2,6-dione derivatives followed by conversion into catalytically active BODOLs for the diethylzinc addition to benzaldehyde

  摘要：

  4-Substituted bicyclo[2.2.2]octane-2,6-diones have been synthesized and tested as substrates in the enantioselective reduction with baker's yeast to give the corresponding hydroxy ketones. It was found that the derivative bearing a TIPSO group at the 4-position was not reduced at all while that with a TBDMSO group gave 87% yield and 46% ee. Other 4-oxy functionalized derivatives were reduced with varying yields (36-87%) and ees (10-82%). The best result was obtained for the 4-Oallyl derivative (80% yield, 82% ee). The hydroxy ketones carrying the benzyloxy and allyloxy groups at the 4-position were converted into the corresponding BODOLs, which were tested as catalysts in the diethylzinc addition to benzaldehyde. In this reaction the ees were 90% and 89%, respectively, which showed that BODOLs substituted at the 4-position are essentially as good catalysts in this reaction as those bearing a hydrogen. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.06.003
• 作为产物：
  描述：

  1,3-环己二酮 在 乙酸异丙烯酯 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 84.0h， 生成 5,5-Dimethoxy-bicyclo[2.2.2]oct-2-en-1-ol
  参考文献：
  名称：

  桥头羟基双环[2.2.2]辛烷衍生物的合成1

  摘要：

  描述了从1，3-环己二酮开始，向4-羟基双环[2.2.2]辛烷-2，6-二酮衍生物3的两个独立的合成路线。

  DOI：

  10.1021/jo051284e