2-((2R,5R)-5-(hydroxymethyl)-5-vinyltetrahydrofuran-2-yl)propan-2-ol | 1174400-45-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: 2-((2R,5R)-5-(hydroxymethyl)-5-vinyltetrahydrofuran-2-yl)propan-2-ol
• 英文别名: 2-[(2R,5R)-5-ethenyl-5-(hydroxymethyl)oxolan-2-yl]propan-2-ol
• CAS: 1174400-45-3
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: GEFKCBVNZZMNLH-SCZZXKLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (R)-2-methyl-6-methylene-7-octene-2,3-diol 在 吡啶-N-氧化物 、 potassium osmate(VI) dihydrate 、 zinc trifluoromethanesulfonate 、 柠檬酸 、 水 、 sodium sulfite 作用下， 以 水 、 乙腈 为溶剂， 反应 16.0h， 以78%的产率得到2-((2R,5R)-5-(hydroxymethyl)-5-vinyltetrahydrofuran-2-yl)propan-2-ol
  参考文献：
  名称：

  A Lewis Acid Promoted Oxidative Cyclization

  摘要：

  Replacing trifluoroacetic acid with it catalytic amount of Lewis acid in the osmium mediated oxidative cyclization results in higher yielding reactions that can proceed nearly an order of magnitude faster. The osmium loading can also be reduced to as little its 0.2 mol %. Furthermore, these mildly acidic conditions are capable of tolerating a wide range of acid sensitive protecting groups that are incompatible with previous cyclization conditions.

  DOI：

  10.1021/jo901243y

文献信息

• A Lewis Acid Promoted Oxidative Cyclization
  作者：Timothy J. Donohoe、Paul C. M. Winship、Daryl S. Walter

  DOI：10.1021/jo901243y

  日期：2009.8.21

  Replacing trifluoroacetic acid with it catalytic amount of Lewis acid in the osmium mediated oxidative cyclization results in higher yielding reactions that can proceed nearly an order of magnitude faster. The osmium loading can also be reduced to as little its 0.2 mol %. Furthermore, these mildly acidic conditions are capable of tolerating a wide range of acid sensitive protecting groups that are incompatible with previous cyclization conditions.