<2R-(2a(S*),3aα,4α,7α,7aα)>-3-<(octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy>butan-2-on | 135638-10-7

• 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(S*),3aα,4α,7α,7aα)>-3-<(octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy>butan-2-on
• 英文别名: (3S)-3-[[(1R,2S,4R,6S,7R)-1,10,10-trimethyl-3-oxatricyclo[5.2.1.02,6]decan-4-yl]oxy]butan-2-one
• CAS: 135638-10-7
• 化学式: C₁₆H₂₆O₃
• 分子量: 266.381
• InChiKey: LCMSOVYBBWKTJJ-ANGPLYBPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 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(S*),3aα,4α,7α,7aα)>-3-<(octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy>butan-2-on 在 zinc(II) tetrahydroborate 作用下， 以 乙醚 为溶剂， 反应 0.5h， 生成 <2R-(2α(2S*,3S*),3aα,4α,7α,7aα)>-3-<(Octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy>-2-butanol 、 <2R-(2a(2R*,3S*),3aα,4α,7α,7aα)>-3-<(octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy>butan-2-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：

  甲基碘化镁 、 (S)-2-((1R,2S,4R,6S,7R)-1,10,10-Trimethyl-3-oxa-tricyclo[5.2.1.0^2,6]dec-4-yloxy)-propionitrile 以 乙醚 为溶剂， 反应 12.0h， 以74%的产率得到<2R-(2a(S*),3aα,4α,7α,7aα)>-3-<(octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy>butan-2-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.