1,3-Dioxolane-4-methanol, 2,2-dimethyl-5-undecyl-, (4S-trans)- | 150822-77-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3-Dioxolane-4-methanol, 2,2-dimethyl-5-undecyl-, (4S-trans)-
• 英文别名: (2S,3S)-2,3-O-Isopropylidene-1,2,3-tetradecanetriol
• CAS: 150822-77-8
• 化学式: C₁₇H₃₄O₃
• 分子量: 286.455
• InChiKey: IJZIJIJDGXXHOD-HOTGVXAUSA-N

物化性质

• 沸点：
  369.0±17.0 °C(Predicted)
• 密度：
  0.912±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.42
• 重原子数：
  20.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1,3-Dioxolane-4-methanol, 2,2-dimethyl-5-undecyl-, (4S-trans)- 在 吡啶 、 盐酸 作用下， 以 甲醇 为溶剂， 反应 73.0h， 生成 (2S,3S)-1-(Tosyloxy)-2,3-tetradecanediol
  参考文献：
  名称：

  Alkylative epoxide rearrangement. A stereospecific approach to chiral epoxide pheromones

  摘要：

  The alkylative rearrangement of 1,2-epoxy-3-alkanol tosylates is applied to the synthesis of chiral epoxide pheromones. Attack at the terminal carbon atom of epoxy tosylates by lithioacetylenes and cyclization of the intermediate tosyloxy alcohols produces internal epoxides in high yield. The method is stereospecific: threo-epoxy tosylates give eL's-epoxides, and erythro-epoxy tosylates yield trans-epoxides. Several diastereomerically pure epoxides were prepared in high optical purity from chiral pool intermediates derived from sugars. Pheromone components prepared include (+/-)-cis-epoxyalkene 20 and both enantiomers of cis-epoxy diene 16, a female sex pheromone component of a number of lepidopteran species. These results demonstrate that alkylative rearrangement of 1,2-epoxy-3-alkanol tosylates complements existing methods for stereoselective synthesis of epoxides, including the Payne rearrangement and Sharpless epoxidation.

  DOI：

  10.1021/jo00071a026
• 作为产物：
  描述：

  (4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde 在 palladium on activated charcoal 正丁基锂 、 氢气 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 为溶剂， -78.0 ℃ 、262.01 kPa 条件下， 生成 1,3-Dioxolane-4-methanol, 2,2-dimethyl-5-undecyl-, (4S-trans)-
  参考文献：
  名称：

  Alkylative epoxide rearrangement. A stereospecific approach to chiral epoxide pheromones

  摘要：

  The alkylative rearrangement of 1,2-epoxy-3-alkanol tosylates is applied to the synthesis of chiral epoxide pheromones. Attack at the terminal carbon atom of epoxy tosylates by lithioacetylenes and cyclization of the intermediate tosyloxy alcohols produces internal epoxides in high yield. The method is stereospecific: threo-epoxy tosylates give eL's-epoxides, and erythro-epoxy tosylates yield trans-epoxides. Several diastereomerically pure epoxides were prepared in high optical purity from chiral pool intermediates derived from sugars. Pheromone components prepared include (+/-)-cis-epoxyalkene 20 and both enantiomers of cis-epoxy diene 16, a female sex pheromone component of a number of lepidopteran species. These results demonstrate that alkylative rearrangement of 1,2-epoxy-3-alkanol tosylates complements existing methods for stereoselective synthesis of epoxides, including the Payne rearrangement and Sharpless epoxidation.

  DOI：

  10.1021/jo00071a026

文献信息

• Alkylative epoxide rearrangement. A stereospecific approach to chiral epoxide pheromones
  作者：Thomas W. Bell、James A. Ciaccio

  DOI：10.1021/jo00071a026

  日期：1993.9

  The alkylative rearrangement of 1,2-epoxy-3-alkanol tosylates is applied to the synthesis of chiral epoxide pheromones. Attack at the terminal carbon atom of epoxy tosylates by lithioacetylenes and cyclization of the intermediate tosyloxy alcohols produces internal epoxides in high yield. The method is stereospecific: threo-epoxy tosylates give eL's-epoxides, and erythro-epoxy tosylates yield trans-epoxides. Several diastereomerically pure epoxides were prepared in high optical purity from chiral pool intermediates derived from sugars. Pheromone components prepared include (+/-)-cis-epoxyalkene 20 and both enantiomers of cis-epoxy diene 16, a female sex pheromone component of a number of lepidopteran species. These results demonstrate that alkylative rearrangement of 1,2-epoxy-3-alkanol tosylates complements existing methods for stereoselective synthesis of epoxides, including the Payne rearrangement and Sharpless epoxidation.