(1R,2S,6R)-1,10,10-trimethyl-2-(trifluoromethyl)-3,5-dioxa-tricyclo[5.2.1.0^2,6]decan-4-one | 1059189-25-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1R,2S,6R)-1,10,10-trimethyl-2-(trifluoromethyl)-3,5-dioxa-tricyclo[5.2.1.0^2,6]decan-4-one
• 英文别名: (1R,2S,6R,7S)-1,10,10-trimethyl-2-(trifluoromethyl)-3,5-dioxatricyclo[5.2.1.02,6]decan-4-one
• CAS: 1059189-25-1
• 化学式: C₁₂H₁₅F₃O₃
• 分子量: 264.245
• InChiKey: LOFHQCHUJOSNGF-JJHYMCDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (1R,2S,3R)-2-(trifluoromethyl)bornane-2,3-diol 、 N,N'-羰基二咪唑 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以94%的产率得到(1R,2S,6R)-1,10,10-trimethyl-2-(trifluoromethyl)-3,5-dioxa-tricyclo[5.2.1.0^2,6]decan-4-one
  参考文献：
  名称：

  Trifluoromethylation of camphorquinone and its monoimine derivatives

  摘要：

  Treatment of (1R)-camphorquinone 2 with (trifluoromethyl)trimethylsilane in the presence of catalytic amounts of caesium fluoride in DME at room temperature yields two pairs of exo/endo isomers of trifluoromethylated silylated alcohols 5 and 6. In this case, nucleophilic addition of the CF3 anion occurs neither regio- nor stereoselectively. On the other hand, the analogous reaction with (1R)-camphorquinone 3-imines 3, followed by hydrolysis with 5 M HCl in ethanol, leads stereoselectively to (1R,2S)-2-hydroxy-2-(trifluoromethyl)bornan-3-one 8. The attempted reductions of the intermediate adducts with NaBH4 in ethanol gave the corresponding (1R,2S)-3-imino-2-(trifluoromethyl)bornan-2-ols 9 as the sole isomers in high yield. The configuration of C(2), that is, the endo course of the nucleophilic CF3 addition, was proven by X-ray crystallography. Furthermore, the reduction of the C = N bond in 9 with DIBAL-H leads stereoselectively to the exo amino derivatives 10, which, by treatment with phosgene, smoothly form the fused 1,3-oxazolidin-2-ones 11. In contrast, the reduction of ketone 8 yields a Mixture of the exo,exo- and exo,endo-2,3-diols 12. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.07.003