(2S,6S)-1,2-O-isopropylidene-4,8-dioxaundeca-10-en-6-ol | 1452161-50-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,6S)-1,2-O-isopropylidene-4,8-dioxaundeca-10-en-6-ol
• CAS: 1452161-50-0
• 化学式: C₁₂H₂₂O₅
• 分子量: 246.304
• InChiKey: QUAXSGFCTFSNTF-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.72
• 重原子数：
  17.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S,6S)-1,2-O-isopropylidene-4,8-dioxaundeca-10-en-6-ol 在 水 、 溶剂黄146 作用下， 反应 7.0h， 以100%的产率得到
  参考文献：
  名称：

  Short and Stereocontrolled Cyclic Polyglycerols Synthesis Using BF3·OEt2 Mediated Intramolecular Epoxide-Opening Reaction

  摘要：

  We developed a new method for the stereocontrolled synthesis of cyclic oligoglycerols. Optically pure solketal and epichlorohydrin were coupled with allyl alcohol under aqueous basic conditions to construct a linear triglycerol skeleton. After subsequent steps, the epoxy alcohol (7) obtained was treated with a catalytic amount of BF3 center dot OEt2 in CH2Cl2 to produce in a high yield of the desired cyclic triglycerol through a regioselective, intramolecular epoxide ring-opening reaction.

  DOI：

  10.3987/com-12-s(n)67
• 作为产物：
  描述：

  左旋环氧氯丙烷 、 (S)-(+)-1,2-异亚丙基甘油 、 烯丙醇 在 四正丁基硫酸铵 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 26.0h， 以65%的产率得到(2S,6S)-1,2-O-isopropylidene-4,8-dioxaundeca-10-en-6-ol
  参考文献：
  名称：

  Short and Stereocontrolled Cyclic Polyglycerols Synthesis Using BF3·OEt2 Mediated Intramolecular Epoxide-Opening Reaction

  摘要：

  We developed a new method for the stereocontrolled synthesis of cyclic oligoglycerols. Optically pure solketal and epichlorohydrin were coupled with allyl alcohol under aqueous basic conditions to construct a linear triglycerol skeleton. After subsequent steps, the epoxy alcohol (7) obtained was treated with a catalytic amount of BF3 center dot OEt2 in CH2Cl2 to produce in a high yield of the desired cyclic triglycerol through a regioselective, intramolecular epoxide ring-opening reaction.

  DOI：

  10.3987/com-12-s(n)67