(R)-10,14-Dimethyl-7-pentadecanol | 164260-11-1

• 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: (R)-10,14-Dimethyl-7-pentadecanol
• 英文别名: (r)-10,14-Dimethyl-1-pentadecanol；(10R)-10,14-dimethylpentadecan-1-ol
• CAS: 164260-11-1
• 化学式: C₁₇H₃₆O
• 分子量: 256.472
• InChiKey: ZJLZJBDEHQWBHZ-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  18
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  异丁酰氯 、 (R)-10,14-Dimethyl-7-pentadecanol 在 吡啶 、 盐酸 、 碳酸氢钠 作用下， 以 乙醚 为溶剂， 175.0 ℃ 、93.33 Pa 条件下， 生成 (R)-10,14-dimethylpentadecyl isobutyrate
  参考文献：
  名称：

  摘要：

  Field trials were conducted with each synthetic enantiomer(> 98 % ee) and blends of the two synthetic enantiomers of the female-produced sex pheromone (10,14-dimethylpentadecyl isobutyrate) of the tea tussock moth, Euproctis pseudoconspersa. Male moths were attracted to each enantiomer alone and to various blends of them. Short syntheses of both enantiomers of the pheromone from commercially available (R)- and (S)-citronellyl bromide and a method of checking the enantiomeric purity of the citronellyl bromide enantiomers are described.

  DOI：

  10.1023/a:1021226800132
• 作为产物：
  描述：

  (10S)-10,14-dimethylpentadec-13-en-6-yn-1-ol 在 palladium on activated charcoal 氢气 作用下， 以 正己烷 为溶剂， 反应 8.0h， 以83%的产率得到(R)-10,14-Dimethyl-7-pentadecanol
  参考文献：
  名称：

  摘要：

  Field trials were conducted with each synthetic enantiomer(> 98 % ee) and blends of the two synthetic enantiomers of the female-produced sex pheromone (10,14-dimethylpentadecyl isobutyrate) of the tea tussock moth, Euproctis pseudoconspersa. Male moths were attracted to each enantiomer alone and to various blends of them. Short syntheses of both enantiomers of the pheromone from commercially available (R)- and (S)-citronellyl bromide and a method of checking the enantiomeric purity of the citronellyl bromide enantiomers are described.

  DOI：

  10.1023/a:1021226800132

文献信息

• Absolute configuration of sex pheromone for tea tussock moth,Euproctis pseudoconspersa (strand)via synthesis of (R)- and (S)-10, 14-dimethyl-1-pentadecyl isobutyrates
  作者：Akio Ichikawa、Tetsuya Yasuda、Sadao Wakamura

  DOI：10.1007/bf02033705

  日期：1995.5

  (R)- and (S)-10,14-dimethyl-1-pentadecyl isobutyrates were synthesized from (S)- and (R)-citronellols, respectively. TheR enantiomer was as active as the natural pheromone but theS enantiomer was less active in the electrophysiological analyses, which provided conclusive proof that the absolute configuration of the natural pheromone isR.

  (R)-和(S)-10,14-二甲基-1-十五烷基异丁酸酯分别由(S)-和(R)-香茅醇合成。R 对映异构体与天然信息素一样有活性，但 S 对映异构体在电生理分析中活性较低，这为天然信息素的绝对构型为 R 提供了确凿证据。
• ——
  作者：Cheng-Hua Zhao、Jocelyn G. Millar、Kun-Hui Pan、Cai-Sheng Xu

  DOI：10.1023/a:1021226800132

  日期：——

  Field trials were conducted with each synthetic enantiomer(> 98 % ee) and blends of the two synthetic enantiomers of the female-produced sex pheromone (10,14-dimethylpentadecyl isobutyrate) of the tea tussock moth, Euproctis pseudoconspersa. Male moths were attracted to each enantiomer alone and to various blends of them. Short syntheses of both enantiomers of the pheromone from commercially available (R)- and (S)-citronellyl bromide and a method of checking the enantiomeric purity of the citronellyl bromide enantiomers are described.