(2S,4S,6S)-2,4,6,8-tetramethylnonan-1-ol | 1354656-83-9

• 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: (2S,4S,6S)-2,4,6,8-tetramethylnonan-1-ol
• CAS: 1354656-83-9
• 化学式: C₁₃H₂₈O
• 分子量: 200.365
• InChiKey: PRKWWWFQTPBHRO-AVGNSLFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  14
• 可旋转键数：
  7
• 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：

  (2S,4S,6S)-2,4,6,8-tetramethylnonan-1-ol 在 吡啶 、 4-二甲氨基吡啶 、 水 、 三乙胺 、 对甲苯磺酰氯 、 lithium hydroxide 、 双环己基(三氟甲烷磺酰氧基)硼烷 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 6.0h， 生成 (+)-vittatalactone
  参考文献：
  名称：

  A General, Asymmetric, and Noniterative Synthesis of Trideoxypropionates. Straightforward Syntheses of the Pheromones (+)-Vittatalactone and (+)-Norvittatalactone

  摘要：

  A novel, highly stereocontrolled, and very flexible synthetic access to biologically relevant trideoxypropionate building blocks in optically pure form has been developed. On the basis of a three-step sequence comprising a thermal oxy-Cope rearrangement, an iridium-catalyzed hydrogenation, and an auxiliary-controlled enolate methylation, trideoxypropionates with easily adjustable relative configuration were synthesized in excellent yields. In addition, the functionalized end groups allow for chemoselective manipulations and further elongation of the chain. The underlying strategy constitutes the first noniterative process for the assembly of polydeoxypropionates and has further been applied in total syntheses of the pheromones (+)-vittatalactone and (+)-norvittatalactone, which had been isolated from the striped cucumber beetle Acalymma vittatum.

  DOI：

  10.1021/jo202330b
• 作为产物：
  描述：

  C₂₃H₄₀O₃Si 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 potassium carbonate 、 magnesium 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 42.0h， 生成 (2S,4S,6S)-2,4,6,8-tetramethylnonan-1-ol
  参考文献：
  名称：

  A General, Asymmetric, and Noniterative Synthesis of Trideoxypropionates. Straightforward Syntheses of the Pheromones (+)-Vittatalactone and (+)-Norvittatalactone

  摘要：

  A novel, highly stereocontrolled, and very flexible synthetic access to biologically relevant trideoxypropionate building blocks in optically pure form has been developed. On the basis of a three-step sequence comprising a thermal oxy-Cope rearrangement, an iridium-catalyzed hydrogenation, and an auxiliary-controlled enolate methylation, trideoxypropionates with easily adjustable relative configuration were synthesized in excellent yields. In addition, the functionalized end groups allow for chemoselective manipulations and further elongation of the chain. The underlying strategy constitutes the first noniterative process for the assembly of polydeoxypropionates and has further been applied in total syntheses of the pheromones (+)-vittatalactone and (+)-norvittatalactone, which had been isolated from the striped cucumber beetle Acalymma vittatum.

  DOI：

  10.1021/jo202330b

文献信息

• A General, Asymmetric, and Noniterative Synthesis of Trideoxypropionates. Straightforward Syntheses of the Pheromones (+)-Vittatalactone and (+)-Norvittatalactone
  作者：Christian F. Weise、Matthias C. Pischl、Andreas Pfaltz、Christoph Schneider

  DOI：10.1021/jo202330b

  日期：2012.2.3

  A novel, highly stereocontrolled, and very flexible synthetic access to biologically relevant trideoxypropionate building blocks in optically pure form has been developed. On the basis of a three-step sequence comprising a thermal oxy-Cope rearrangement, an iridium-catalyzed hydrogenation, and an auxiliary-controlled enolate methylation, trideoxypropionates with easily adjustable relative configuration were synthesized in excellent yields. In addition, the functionalized end groups allow for chemoselective manipulations and further elongation of the chain. The underlying strategy constitutes the first noniterative process for the assembly of polydeoxypropionates and has further been applied in total syntheses of the pheromones (+)-vittatalactone and (+)-norvittatalactone, which had been isolated from the striped cucumber beetle Acalymma vittatum.