(S)-3-(benzyloxy)-4-methylpentane-1,4-diol | 1353653-49-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-3-(benzyloxy)-4-methylpentane-1,4-diol
• CAS: 1353653-49-2
• 化学式: C₁₃H₂₀O₃
• 分子量: 224.3
• InChiKey: IENOBBUGANVTOP-LBPRGKRZSA-N

物化性质

• 沸点：
  376.3±27.0 °C(Predicted)
• 密度：
  1.085±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.73
• 重原子数：
  16.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  49.69
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-3-(benzyloxy)-4-methylpentane-1,4-diol 在 重铬酸吡啶 、 正丁基锂 、 potassium hydride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 环己烷 为溶剂， 反应 25.0h， 生成 (S)-(((2-methyl-2-((2-methylallyl)oxy)undec-5-en-3-yl)oxy)methyl)benzene
  参考文献：
  名称：

  Ring-closing metathesis and palladium-catalyzed formate reduction to 3-methyleneoxepanes. Formal synthesis of (−)-zoapatanol

  摘要：

  A sequence of ring-closing metathesis and palladium-catalyzed formate reduction was developed for preparing O-heterocycles with an exocyclic olefin and applied to the asymmetric synthesis of zoapatanol. The key vicinal stereocenters in zoapatanol were constructed from the L-malic acid-derived lactone by successive chelation-controlled addition of alkyl groups. The O-allylations to prepare the dienes for RCM were achieved with the tertiary alcohols bearing internal olefins. The ring opening of oxepane, a new reaction pathway for the Pd-formate reduction, is also reported. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.10.023
• 作为产物：
  描述：

  甲基溴化镁 、 (S)-3-(benzyloxy)dihydrofuran-2(3H)-one 在 氯化铵 作用下， 以 乙醚 、 水 为溶剂， 反应 1.5h， 以92%的产率得到(S)-3-(benzyloxy)-4-methylpentane-1,4-diol
  参考文献：
  名称：

  Ring-closing metathesis and palladium-catalyzed formate reduction to 3-methyleneoxepanes. Formal synthesis of (−)-zoapatanol

  摘要：

  A sequence of ring-closing metathesis and palladium-catalyzed formate reduction was developed for preparing O-heterocycles with an exocyclic olefin and applied to the asymmetric synthesis of zoapatanol. The key vicinal stereocenters in zoapatanol were constructed from the L-malic acid-derived lactone by successive chelation-controlled addition of alkyl groups. The O-allylations to prepare the dienes for RCM were achieved with the tertiary alcohols bearing internal olefins. The ring opening of oxepane, a new reaction pathway for the Pd-formate reduction, is also reported. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.10.023