(3S,5R)-5-(12-tridecenyl)-tetrahydrofuran-3-ol | 1404497-41-1

• 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: (3S,5R)-5-(12-tridecenyl)-tetrahydrofuran-3-ol
• 英文别名: (3S,5R)-5-tridec-12-enyloxolan-3-ol
• CAS: 1404497-41-1
• 化学式: C₁₇H₃₂O₂
• 分子量: 268.44
• InChiKey: ILYKFXPAFREVNA-DLBZAZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  19
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  13-bromo-1-tridecene 在 二正丁基氧化锡 、 magnesium 、 溶剂黄146 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 27.5h， 生成 (2S, 4R)-2,4-dihydroxyheptadec-16-enyl 4-methylbenzene sulfonate 、 (3S,5R)-5-(12-tridecenyl)-tetrahydrofuran-3-ol
  参考文献：
  名称：

  Serendipitous synthesis of 3-hydroxy tetrahydrofurans from tin catalyzed sulfonylation of acyclic 1,2,4-triols

  摘要：

  The reaction of syn-1,2,4-triols under sulfonylation conditions catalyzed by Bu2SnO (5 mol %) results in cyclization and the formation of 3-hydroxy tetrahydrofurans (56-85%) while the anti-1,2,4-triols react to give C1-O-sulfonyl derivatives in good yields (66-83%) and the cyclization product in poor yield (5-12%). A mechanism that justifies these observations is proposed to occur via the tosylation of the primary hydroxyl followed by an intramolecular tin acetal rearrangement to a 1,3-stannylene which then undergoes a 5-exo-tet-cyclization. The difference in rates of cyclization reactivity is due to the energetically more stable tin acetals of syn-1,3-diols compared to those of anti-1,3-diols. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.08.110

文献信息

• Serendipitous synthesis of 3-hydroxy tetrahydrofurans from tin catalyzed sulfonylation of acyclic 1,2,4-triols
  作者：Makhosazana P. Gamedze、Rejoice B. Maseko、Fidelis Chigondo、Comfort M. Nkambule

  DOI：10.1016/j.tetlet.2012.08.110

  日期：2012.10

  The reaction of syn-1,2,4-triols under sulfonylation conditions catalyzed by Bu2SnO (5 mol %) results in cyclization and the formation of 3-hydroxy tetrahydrofurans (56-85%) while the anti-1,2,4-triols react to give C1-O-sulfonyl derivatives in good yields (66-83%) and the cyclization product in poor yield (5-12%). A mechanism that justifies these observations is proposed to occur via the tosylation of the primary hydroxyl followed by an intramolecular tin acetal rearrangement to a 1,3-stannylene which then undergoes a 5-exo-tet-cyclization. The difference in rates of cyclization reactivity is due to the energetically more stable tin acetals of syn-1,3-diols compared to those of anti-1,3-diols. (C) 2012 Elsevier Ltd. All rights reserved.