(3S,4S)-3-(benzyloxy)-4-methylnonane-1,4-diol | 1353653-33-4

• 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: (3S,4S)-3-(benzyloxy)-4-methylnonane-1,4-diol
• CAS: 1353653-33-4
• 化学式: C₁₇H₂₈O₃
• 分子量: 280.408
• InChiKey: HWGQHWBEPGITPA-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.29
• 重原子数：
  20.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 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：

  (3S,4S)-3-(benzyloxy)-4-methylnonane-1,4-diol 在 重铬酸吡啶 、 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、2.07 MPa 条件下， 反应 18.0h， 生成 (4S,5S)-4,5-dihydro-4-hydroxy-5-methyl-5-pentyl-2-(3H)-furanone
  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：

  (S)-3-(benzyloxy)dihydrofuran-2(3H)-one 以 四氢呋喃 为溶剂， 反应 15.0h， 生成 (3S,4S)-3-(benzyloxy)-4-methylnonane-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