(1R)-5β-hydroxy-6β-ketocineole | 1428786-29-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R)-5β-hydroxy-6β-ketocineole
• 英文别名: (1R,4S,5S)-5-hydroxy-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-one
• CAS: 1428786-29-1
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: MICGFUFHVOJCKX-MHYGZLNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  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