| 1440959-41-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• CAS: 1440959-41-0
• 化学式: C₁₅H₂₂O₄
• 分子量: 266.337
• InChiKey: DWGHJUIXNDQDGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  在 2,6-二甲基吡啶 、 三乙基硅烷 、 bismuth(III) bromide 、 三乙基硼 、 三正丁基氢锡 、 三氧化硫吡啶 、 二异丁基氢化铝 、 magnesium bromide ethyl etherate 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 以 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 22.25h， 生成 (±)-(S)-methyl 2-((2S,6R)-6-(2-(benzyloxy)ethyl)tetrahydro-2H-pyran-2-yl)propanoate
  参考文献：
  名称：

  A Study of Exocyclic Radical Reductions of Polysubstituted Tetrahydropyrans

  摘要：

  Exocyclic radical reductions were thoroughly investigated in the context of the synthesis of polysubstituted tetrahydropyrans, Which are found in numerous macrolides. The radical precursors studied herein were generated by tandem cycloetherification and iodoetherification reactions or, alternatively, by semicyclic acetals substitutions. DFT calculations (BHandHLYP/TZVP) performed at the transition-state level for the hydrogen radical delivery are in good accordance with the experimental data and enabled the identification of important conformational factors that govern the selectivities obtained. This study demonstrates:that both the preferred reactive conformation of the radical and steric interactions with the incoming hydride have to be considered in order to fully rationalize the levels of diastereoselection generated in acyclic free-radical processes.

  DOI：

  10.1021/jo400721e