icosyl (2S)-2-methyloctanoate | 181874-25-9

• 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: icosyl (2S)-2-methyloctanoate
• CAS: 181874-25-9
• 化学式: C₂₉H₅₈O₂
• 分子量: 438.778
• InChiKey: ZJEANSGXTSHKAG-NDEPHWFRSA-N

物化性质

• 沸点：
  467.2±13.0 °C(Predicted)
• 密度：
  0.858±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  13.6
• 重原子数：
  31
• 可旋转键数：
  26
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  icosyl (2S)-2-methyloctanoate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 2.0h， 生成 (2S)-2-methyloctan-1-ol
  参考文献：
  名称：

  Resolution of 2-Methylalkanoic Acids. Enantioselective Esterification with Long Chain Alcohols Catalysed by Candida rugosa Lipase.

  摘要：

  Candida rugosa lipase catalysed resolutions of 2-methylalkanoic acids run on a large scale often display decreased enantiomeric rations (E-values) and reaction rates compared with small-scale experiments. By continuous control of the water activity (addition of inorganic salt/hydrated salt mixtures) this can be avoided. The importance of the proper choice of alcohol as well as its concentration is demonstrated. (R)-2-Methyloctanoic acid (8.6g) and (S)-2-methyl-l-octanol (4.5 g), both in 99.6% ee were prepared from 20 g racemic 2-methyloctanoic acid.

  DOI：

  10.3891/acta.chem.scand.50-0666
• 作为产物：
  描述：

  1-二十醇 、 2-甲基辛酸 在 磷脂酶B sodium sulfate 作用下， 以 环己烷 、 水 为溶剂， 以44%的产率得到icosyl (2S)-2-methyloctanoate
  参考文献：
  名称：

  Resolution of 2-Methylalkanoic Acids. Enantioselective Esterification with Long Chain Alcohols Catalysed by Candida rugosa Lipase.

  摘要：

  Candida rugosa lipase catalysed resolutions of 2-methylalkanoic acids run on a large scale often display decreased enantiomeric rations (E-values) and reaction rates compared with small-scale experiments. By continuous control of the water activity (addition of inorganic salt/hydrated salt mixtures) this can be avoided. The importance of the proper choice of alcohol as well as its concentration is demonstrated. (R)-2-Methyloctanoic acid (8.6g) and (S)-2-methyl-l-octanol (4.5 g), both in 99.6% ee were prepared from 20 g racemic 2-methyloctanoic acid.

  DOI：

  10.3891/acta.chem.scand.50-0666

文献信息

• Resolution of 2-Methylalkanoic Acids. Enantioselective Esterification with Long Chain Alcohols Catalysed by Candida rugosa Lipase.
  作者：H. Edlund、P. Berglund、M. Jensen、E. Hedenström、H.-E. Högberg、Frode Rise、Kjell Undheim、Connie N. Rosendahl、Monika Haugg、Nathalie Trabesinger-Rüf、Elmar G. Weinhold

  DOI：10.3891/acta.chem.scand.50-0666

  日期：——

  Candida rugosa lipase catalysed resolutions of 2-methylalkanoic acids run on a large scale often display decreased enantiomeric rations (E-values) and reaction rates compared with small-scale experiments. By continuous control of the water activity (addition of inorganic salt/hydrated salt mixtures) this can be avoided. The importance of the proper choice of alcohol as well as its concentration is demonstrated. (R)-2-Methyloctanoic acid (8.6g) and (S)-2-methyl-l-octanol (4.5 g), both in 99.6% ee were prepared from 20 g racemic 2-methyloctanoic acid.