Acetic acid (1R,4S,6S)-1,3,3-trimethyl-2-oxa-bicyclo[2.2.2]oct-6-yl ester | 57709-95-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: Acetic acid (1R,4S,6S)-1,3,3-trimethyl-2-oxa-bicyclo[2.2.2]oct-6-yl ester
• 英文别名: (1R,4S,6S)-1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octan-6-yl acetate；[(1R,4S,6S)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-yl] acetate
• CAS: 57709-95-2
• 化学式: C₁₂H₂₀O₃
• 分子量: 212.289
• InChiKey: XRKZFZWIYZDOQO-JBLDHEPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  2
• 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：
  3

反应信息

• 作为产物：
  描述：

  (1R,4S,6S)-2-hydroxy-1,8-cineole (S)-O-methylmandelate ester 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 Acetic acid (1R,4S,6S)-1,3,3-trimethyl-2-oxa-bicyclo[2.2.2]oct-6-yl ester
  参考文献：
  名称：

  Enantiomeric Purity and Odor Characteristics of 2- and 3-Acetoxy-1,8-cineoles in the Rhizomes of Alpinia galanga Willd.

  摘要：

  (S)-(+)-O-methylmandelate esters of trans- and cis-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-5- and 6-ols (2- and 3-hydroxy-1,8-cineoles) were prepared, and eight diastereomers were separated. The absolute configuration of the asymmetric carbons of the cineole moiety of each diastereomer was determined by H-1 NMR data according to the Mosher theory. Each mandelate was reduced with LiAlHe4 to obtain optically pure hydroxy-1,8-cineoles, this being followed by acetylation to afford optically pure acetoxy-1,8-cineoles. These acetates were subjected to chiral GC, using a cyclodextrin column, and the enantiomeric purity of trans- and cis-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-5- and 6-yl acetates in the aroma concentrate from the rhizomes of Alpinia galanga was determined as 93.9 (5S), 19.4 (5R), 63.5 (6R), and 100 (6R) % cc, respectively. The aroma character of each enantiomer was also evaluated by GC-sniffing.

  DOI：

  10.1021/jf9807465