(4S,8R)-4,8-dimethyldecyl acetate | 1262552-74-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (4S,8R)-4,8-dimethyldecyl acetate
• CAS: 1262552-74-8
• 化学式: C₁₄H₂₈O₂
• 分子量: 228.375
• InChiKey: BPOWBJYGBRSCBI-OLZOCXBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 重原子数：
  16.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  (4R,8S)-4,8-dimethyldecan-1-ol 、 乙酸酐 在 吡啶 作用下， 生成 (4S,8R)-4,8-dimethyldecyl acetate
  参考文献：
  名称：

  Pheromone synthesis. Part 245: Synthesis and chromatographic analysis of the four stereoisomers of 4,8-dimethyldecanal, the male aggregation pheromone of the red flour beetle, Tribolium castaneum

  摘要：

  All four stereoisomers of 4,8-dimethyldecanal (1) were synthesized from the enantiomers of 2-methyl-1-butanol and citronellal. Enantioselective GC analysis enabled separation of (4R,8R)-1 and (4R,8S)-1 from a mixture of (45,8R)-1 and (4S,8S)-1, when octakis-(2,3-di-O-methoxymethyl-6-O-tert-butyldimethylsilyl)-gamma-cyclodextrin was employed as a chiral stationary phase. Complete separation of the four stereoisomers of 1 on reversed-phase HPLC at -54 degrees C was achieved after oxidation of 1 to the corresponding carboxylic acid 12 followed by its derivatization with (1R,2R)-2-(2,3-anthracenedicarboximido) cyclohexanol, and the natural 1 was found to be a mixture of all the four stereoisomers. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.10.086