<2R-(2a(R*),3aα,4α,7α,7aα)>-2-methyl-8-<(octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy>octadecan-7-on | 132881-35-7

• 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: <2R-(2a(R*),3aα,4α,7α,7aα)>-2-methyl-8-<(octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy>octadecan-7-on
• 英文别名: (8R)-2-methyl-8-[[(1R,2S,4R,6S,7R)-1,10,10-trimethyl-3-oxatricyclo[5.2.1.02,6]decan-4-yl]oxy]octadecan-7-one
• CAS: 132881-35-7
• 化学式: C₃₁H₅₆O₃
• 分子量: 476.784
• InChiKey: HHSUZLQCCJOENL-CAPOSIETSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  34
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  <2R-(2a(R*),3aα,4α,7α,7aα)>-2-methyl-8-<(octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy>octadecan-7-on 在 zinc(II) tetrahydroborate 作用下， 以 乙醚 为溶剂， 反应 0.5h， 生成 <2R-(2a(7R*,8R*),3aα,4α,7α,7aα)>-2-methyl-8-<(octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy>octadecan-7-ol 、 <2R-(2a(7S*,8R*),3aα,4α,7α,7aα)>-2-methyl-8-<(octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy>octadecan-7-ol
  参考文献：
  名称：

  Pheromone, 3.Mitt.: Eine einfache Methode zur Steuerung der Reduktion von ?-Alkoxy-carbonylverbindungen

  摘要：

  Enantiomerically pure 1,2-diols bearing optionally syn or anti configurated secondary hydroxylic groups are synthesized from acetal-protected cyanohydrins. After resolution of the diastereomers the cyanohydrins are converted into alpha-alkoxy-ketones by Grignard-reaction followed by reduction using common chelating or non-chelating agents. Among others syntheses of enantiomerically pure pheromones, endo-Brevicomin, exo-Brevicomin and Dispalure are given as examples.

  DOI：

  10.1007/bf00810831
• 作为产物：
  描述：

  (RS)-2-hydroxy-dodecanenitrile 在 对甲苯磺酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.25h， 生成 <2R-(2a(R*),3aα,4α,7α,7aα)>-2-methyl-8-<(octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy>octadecan-7-on
  参考文献：
  名称：

  Pheromone, 3.Mitt.: Eine einfache Methode zur Steuerung der Reduktion von ?-Alkoxy-carbonylverbindungen

  摘要：

  Enantiomerically pure 1,2-diols bearing optionally syn or anti configurated secondary hydroxylic groups are synthesized from acetal-protected cyanohydrins. After resolution of the diastereomers the cyanohydrins are converted into alpha-alkoxy-ketones by Grignard-reaction followed by reduction using common chelating or non-chelating agents. Among others syntheses of enantiomerically pure pheromones, endo-Brevicomin, exo-Brevicomin and Dispalure are given as examples.

  DOI：

  10.1007/bf00810831

文献信息

• Pheromone, 3.Mitt.: Eine einfache Methode zur Steuerung der Reduktion von ?-Alkoxy-carbonylverbindungen
  作者：Christian R. Noe、M. Knollm�ller、G. Steinbauer、E. Wagner、H. K�rner、P. Ettmayer、H. V�llenkle

  DOI：10.1007/bf00810831

  日期：1991.4

  Enantiomerically pure 1,2-diols bearing optionally syn or anti configurated secondary hydroxylic groups are synthesized from acetal-protected cyanohydrins. After resolution of the diastereomers the cyanohydrins are converted into alpha-alkoxy-ketones by Grignard-reaction followed by reduction using common chelating or non-chelating agents. Among others syntheses of enantiomerically pure pheromones, endo-Brevicomin, exo-Brevicomin and Dispalure are given as examples.