threo-(2R,3R)-1,2-Epoxy-3-tetradecanol | 136598-27-1

• 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: threo-(2R,3R)-1,2-Epoxy-3-tetradecanol
• 英文别名: (2R,3R)-1,2-epoxy-3-hydroxytetradecane；(2r,3r)-1,2-Epoxytetradecan-3-ol；(1R)-1-[(2R)-oxiran-2-yl]dodecan-1-ol
• CAS: 136598-27-1
• 化学式: C₁₄H₂₈O₂
• 分子量: 228.375
• InChiKey: DTJNQTGZYVCTIX-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  16
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  threo-(2R,3R)-1,2-Epoxy-3-tetradecanol 在 吡啶 、 正丁基锂 、 三氟化硼乙醚 、 potassium carbonate 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 26.17h， 生成 噁丙环,2-(2,5-辛二炔基)-3-十一烷基-,(2S,3R)-
  参考文献：
  名称：

  Tolstikov, A. G.; Khakhalina, N. V.; Spirikhin, L. V., Journal of Organic Chemistry USSR (English Translation), 1991, vol. 27, # 4.2, p. 679 - 684

  摘要：

  DOI：
• 作为产物：
  描述：

  undecylmagnesium bromide 在 吡啶 、 盐酸 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 82.25h， 生成 threo-(2R,3R)-1,2-Epoxy-3-tetradecanol
  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

• TOLSTIKOV, A. G.;XAXALINA, N. V.;SPIRIXIN, L. V.;XALILOV, L. M.;PANASENKO+, ZH. ORGAN. XIMII, 27,(1991) N, S. 792-798
  作者：TOLSTIKOV, A. G.、XAXALINA, N. V.、SPIRIXIN, L. V.、XALILOV, L. M.、PANASENKO+

  DOI：——

  日期：——
• 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.
• Tolstikov, A. G.; Khakhalina, N. V.; Spirikhin, L. V., Journal of Organic Chemistry USSR (English Translation), 1991, vol. 27, # 4.2, p. 679 - 684
  作者：Tolstikov, A. G.、Khakhalina, N. V.、Spirikhin, L. V.、Khalilov, L. M.、Panasenko, A. A.、et al.

  DOI：——

  日期：——