(2R,4S)-4-methylhexane-1,2,6-triol | 1427207-35-9

• 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: (2R,4S)-4-methylhexane-1,2,6-triol
• 英文别名: (2R,4S)-4-methylhexan-1,2,6-triol
• CAS: 1427207-35-9
• 化学式: C₇H₁₆O₃
• 分子量: 148.202
• InChiKey: ASIVSHMOKCMYPA-NKWVEPMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,4S)-4-methylhexane-1,2,6-triol 在 重铬酸吡啶 、 periodic acid dihydrate 、 4-甲基苯磺酸吡啶 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 38.25h， 生成 ethyl (2E,5S)-7,7-dimethoxy-5-methylhept-2-enoate
  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-(hydroxymethyl)-4-methyltetrahydro-2H-pyran-2-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到(2R,4S)-4-methylhexane-1,2,6-triol
  参考文献：
  名称：

  (4R,6R)-6-(hydroxymethyl)-4-methyltetrahydro-2H-pyran-2-one in the synthesis of polyfunctional compounds with the methyl-branched carbon skeleton

  摘要：

  A simple and efficient asymmetrical synthesis was performed of a convenient bifunctional building block, methyl (R)-5,5-dimethoxy-3-methylpentanoate and its (S)-enantiomer. The possibility was shown of its application to the synthesis of insect pheromones.

  DOI：

  10.1134/s1070428013020127