(2R,3R)-1-Iodo-2,3-pentadecanediol | 165601-78-5

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: (2R,3R)-1-Iodo-2,3-pentadecanediol
• 英文别名: (2S,3R)-1-iodopentadecane-2,3-diol
• CAS: 165601-78-5
• 化学式: C₁₅H₃₁IO₂
• 分子量: 370.314
• InChiKey: QSLFCGNAHKEWGH-HUUCEWRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  18
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,3R)-1-Iodo-2,3-pentadecanediol 在 sodium hydroxide 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 2.5h， 生成 2-((2R,3R)-2,3-Dihydroxy-pentadecyl)-malonic acid
  参考文献：
  名称：

  C-1 Reactivity of 2,3-Epoxy Alcohols via Oxirane Opening with Metal Halides: Applications and Synthesis of Naturally Occurring 2,3-Octanediol, Muricatacin, 3-Octanol, and 4-Dodecanolide

  摘要：

  The C-1 reactivity of 2,3-epoxy alcohols and derivatives has been examined thoroughly. In the first approach a rearrangement opening of 2,3-epoxy alcohols with LiI leads to 1-iodo 2,3-diols with erythro or three stereochemistry starting from trans or cis epoxy alcohols. Subsequent coupling with a carbon nucleophile can lead to a series of vicinal diols with predicted relative and absolute stereochemistry: the described methodology has been applied to the asymmetric synthesis of the naturally occurring (S,S)-2,3-octanediol and (R,R)-muricatacin. The second approach, starting from easily available tosyloxy epoxides, leads to the highly regioselective opening of the oxirane ring with Li halides. The 3-iodohydrins obtained can be reduced to the corresponding 1-(tosyloxy)alkan-2-ols and then coupled with common carbon nucleophiles to afford, in high yields, optically active alcohols. This methodology has been applied to the asymmetric synthesis of naturally occurring pheromones like 3(R)-octanol and 4(R)-dodecanolide.

  DOI：

  10.1021/jo00120a025
• 作为产物：
  描述：

  (2R,3R)-2,3-Epoxypentadecan-1-ol 在 lithium iodide 作用下， 以 乙二醇二甲醚 为溶剂， 反应 7.0h， 以70%的产率得到(2R,3R)-1-Iodo-2,3-pentadecanediol
  参考文献：
  名称：

  C-1 Reactivity of 2,3-Epoxy Alcohols via Oxirane Opening with Metal Halides: Applications and Synthesis of Naturally Occurring 2,3-Octanediol, Muricatacin, 3-Octanol, and 4-Dodecanolide

  摘要：

  The C-1 reactivity of 2,3-epoxy alcohols and derivatives has been examined thoroughly. In the first approach a rearrangement opening of 2,3-epoxy alcohols with LiI leads to 1-iodo 2,3-diols with erythro or three stereochemistry starting from trans or cis epoxy alcohols. Subsequent coupling with a carbon nucleophile can lead to a series of vicinal diols with predicted relative and absolute stereochemistry: the described methodology has been applied to the asymmetric synthesis of the naturally occurring (S,S)-2,3-octanediol and (R,R)-muricatacin. The second approach, starting from easily available tosyloxy epoxides, leads to the highly regioselective opening of the oxirane ring with Li halides. The 3-iodohydrins obtained can be reduced to the corresponding 1-(tosyloxy)alkan-2-ols and then coupled with common carbon nucleophiles to afford, in high yields, optically active alcohols. This methodology has been applied to the asymmetric synthesis of naturally occurring pheromones like 3(R)-octanol and 4(R)-dodecanolide.

  DOI：

  10.1021/jo00120a025