(2S,3S,4S)-2-pentyl-1-oxaspiro[4.5]decane-3,4-diol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4S)-2-pentyl-1-oxaspiro[4.5]decane-3,4-diol
• 化学式: C₁₄H₂₆O₃
• 分子量: 242.359
• InChiKey: ACGRVSOJIAXSFY-XQQFMLRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S)-2-pentyl-1-oxaspiro[4.5]decane-3,4-diol 、 tert-butyldimethylsilyl triflate 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (2S,3S,4S)-3-(tert-butyldimethylsilyloxy)-2-pentyl-1-oxaspiro[4.5]decan-4-ol
  参考文献：
  名称：

  Regioselective and Stereoselective Cyclizations of Chloropolyols in Water: Rapid Synthesis of Hydroxytetrahydrofurans

  摘要：

  A concise, stereoselective synthesis of functionalized tetrahydrofuranols has been developed that involves heating readily available chloropolyols in water. These reactions are operationally straightforward and chemoselective for the formation of tetrahydrofurans, obviating the need for complicated protecting group strategies. The efficiency of this process is demonstrated in a short asymmetric synthesis of the natural product (+)-goniothalesdiol.

  DOI：

  10.1021/ol100260z
• 作为产物：
  描述：

  (1S,2S,3R)-3-chloro-1-(1-hydroxycyclohexyl)octane-1,2-diol 以 水 为溶剂， 反应 0.33h， 以94%的产率得到(2S,3S,4S)-2-pentyl-1-oxaspiro[4.5]decane-3,4-diol
  参考文献：
  名称：

  Regioselective and Stereoselective Cyclizations of Chloropolyols in Water: Rapid Synthesis of Hydroxytetrahydrofurans

  摘要：

  A concise, stereoselective synthesis of functionalized tetrahydrofuranols has been developed that involves heating readily available chloropolyols in water. These reactions are operationally straightforward and chemoselective for the formation of tetrahydrofurans, obviating the need for complicated protecting group strategies. The efficiency of this process is demonstrated in a short asymmetric synthesis of the natural product (+)-goniothalesdiol.

  DOI：

  10.1021/ol100260z

文献信息

• Regioselective and Stereoselective Cyclizations of Chloropolyols in Water: Rapid Synthesis of Hydroxytetrahydrofurans
  作者：Baldip Kang、Stanley Chang、Shannon Decker、Robert Britton

  DOI：10.1021/ol100260z

  日期：2010.4.16

  A concise, stereoselective synthesis of functionalized tetrahydrofuranols has been developed that involves heating readily available chloropolyols in water. These reactions are operationally straightforward and chemoselective for the formation of tetrahydrofurans, obviating the need for complicated protecting group strategies. The efficiency of this process is demonstrated in a short asymmetric synthesis of the natural product (+)-goniothalesdiol.