(3S,5R)-6-(benzyloxy)-3-methylhexane-1,5-diol | 1580448-84-5

• 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,5R)-6-(benzyloxy)-3-methylhexane-1,5-diol
• 英文别名: (3S,5R)-3-methyl-6-phenylmethoxyhexane-1,5-diol
• CAS: 1580448-84-5
• 化学式: C₁₄H₂₂O₃
• 分子量: 238.327
• InChiKey: UMGMIETZPUQAKS-GXTWGEPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,5R)-6-(benzyloxy)-3-methylhexane-1,5-diol 在 lithium aluminium tetrahydride 、 氨 、 sodium 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.0h， 生成 (S)-(+)-4-甲基-1-己醇
  参考文献：
  名称：

  (3S,5R)-6-(benzyloxy)-3-methylhexane-1,5-diol in the synthesis of insect pheromones with methyl-branched carbon chain and of amphidinolide L C 7 –C 14 fragment

  摘要：

  New building block (3S,5R)-6-(benzyloxy)-3-methylhexane-1,5-diol was obtained, and based thereon new formal syntheses of (Z)-trogodermal, a component of the sex pheromone of smaller tea tortrix and of the alarm pheromone of ants of genus Crematogaster were suggested. A new synthetic protocol for (3S)-5-methyl-5-oxopentyl acetate and (3S)-5-(benzyloxy)-3-methylpentanal, convenient building blocks for insect pheromones designing was developed. A new simple and efficient asymmetric synthesis of C-7-C-14 fragment of the cytotoxic macrolactone amphidinolide L was carried out.

  DOI：

  10.1134/s1070428014020043
• 作为产物：
  描述：

  (4R,6R)-6-(benzyloxymethyl)-4-methyltetrahydro-2H-pyran-2-one 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 0.5h， 以98%的产率得到(3S,5R)-6-(benzyloxy)-3-methylhexane-1,5-diol
  参考文献：
  名称：

  (3S,5R)-6-(benzyloxy)-3-methylhexane-1,5-diol in the synthesis of insect pheromones with methyl-branched carbon chain and of amphidinolide L C 7 –C 14 fragment

  摘要：

  New building block (3S,5R)-6-(benzyloxy)-3-methylhexane-1,5-diol was obtained, and based thereon new formal syntheses of (Z)-trogodermal, a component of the sex pheromone of smaller tea tortrix and of the alarm pheromone of ants of genus Crematogaster were suggested. A new synthetic protocol for (3S)-5-methyl-5-oxopentyl acetate and (3S)-5-(benzyloxy)-3-methylpentanal, convenient building blocks for insect pheromones designing was developed. A new simple and efficient asymmetric synthesis of C-7-C-14 fragment of the cytotoxic macrolactone amphidinolide L was carried out.

  DOI：

  10.1134/s1070428014020043