(1R)-5β-(t-butyldimethylsilanoxy)-6-ketocineole | 1428786-32-6

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (1R)-5β-(t-butyldimethylsilanoxy)-6-ketocineole
• CAS: 1428786-32-6
• 化学式: C₁₆H₃₀O₃Si
• 分子量: 298.498
• InChiKey: NMGCULOHEZYIEY-MQIPJXDCSA-N

反应信息

• 作为反应物：
  描述：

  (1R)-5β-(t-butyldimethylsilanoxy)-6-ketocineole 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.25h， 以41%的产率得到(1R)-5β-hydroxy-6β-ketocineole
  参考文献：
  名称：

  Synthesis of oxygenated cineole derivatives from cineole: utility of cytochrome P450cin as an enantioselective catalyst

  摘要：

  The oxidation of cineole to (1R)-6 beta-hydroxycineole by cytochrome P450(cin) (CYP176A) is utilised as the initial step in the synthesis of a range of compounds, both novel and ones previously known only as race-mates. The potential of P450(cin) to provide useful, enantiopure building blocks is thus demonstrated. In particular, hydroxylation by this enzyme was used as the initial step in the synthesis of a range of functionalised cineole derivatives that could be used as mechanistic probes to elucidate the effect of substrate structure on the transformations mediated by P450(cin). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.02.004
• 作为产物：
  描述：

  在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以0.52 g的产率得到(1R)-5β-(t-butyldimethylsilanoxy)-6-ketocineole
  参考文献：
  名称：

  Synthesis of oxygenated cineole derivatives from cineole: utility of cytochrome P450cin as an enantioselective catalyst

  摘要：

  The oxidation of cineole to (1R)-6 beta-hydroxycineole by cytochrome P450(cin) (CYP176A) is utilised as the initial step in the synthesis of a range of compounds, both novel and ones previously known only as race-mates. The potential of P450(cin) to provide useful, enantiopure building blocks is thus demonstrated. In particular, hydroxylation by this enzyme was used as the initial step in the synthesis of a range of functionalised cineole derivatives that could be used as mechanistic probes to elucidate the effect of substrate structure on the transformations mediated by P450(cin). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.02.004