(S)-5-Methyl-decanoic acid

• 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)-5-Methyl-decanoic acid
• 英文别名: (5S)-5-methyldecanoic acid
• 化学式: C₁₁H₂₂O₂
• 分子量: 186.294
• InChiKey: BDUUYZWYAVGTOK-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,4-苯二胺,N4-环丙基-2-甲基- 、 1-十六烷醇 在 immobilised Candida rugosa Lipase sodium sulfate 作用下， 以 环己烷 为溶剂， 反应 14.4h， 生成 (-)(R)-5-methyl-decanoic acid-(1) 、 (S)-5-Methyl-decanoic acid 、 (R)-5-Methyl-decanoic acid hexadecyl ester
  参考文献：
  名称：

  Do enzymes recognise remotely located stereocentres? Highly enantioselective Candida rugosa lipase-catalysed esterification of the 2- to 8-methyldecanoic acids

  摘要：

  Several racemic methyl decanoic acids have been synthesised and Successfully resolved in esterification with 1-hexadecanol at a(w)=0.8 in cyclohexane using immobilised Candida rugosa lipase (CRL) as the catalyst. The enantiomeric ratios (E=2.8-68) obtained were surprisingly high even when the methyl group was as remotely located as in 8-methyldecanoic acid (E=25). Interestingly, the lipase shows enantiopreference for the S-enantiomer when the methyl group is located on even numbered carbons i.e. for the 2-,4-,6- and 8-methyldecanoic acids and to the R-enantiomer when the methyl group is located on uneven numbered carbons i.e. for the 3-,5- and 7-methyldecanoic acids. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(02)00172-6

文献信息

• Do enzymes recognise remotely located stereocentres? Highly enantioselective Candida rugosa lipase-catalysed esterification of the 2- to 8-methyldecanoic acids
  作者：Erik Hedenström、Ba-Vu Nguyen、Louis A. Silks

  DOI：10.1016/s0957-4166(02)00172-6

  日期：2002.5

  Several racemic methyl decanoic acids have been synthesised and Successfully resolved in esterification with 1-hexadecanol at a(w)=0.8 in cyclohexane using immobilised Candida rugosa lipase (CRL) as the catalyst. The enantiomeric ratios (E=2.8-68) obtained were surprisingly high even when the methyl group was as remotely located as in 8-methyldecanoic acid (E=25). Interestingly, the lipase shows enantiopreference for the S-enantiomer when the methyl group is located on even numbered carbons i.e. for the 2-,4-,6- and 8-methyldecanoic acids and to the R-enantiomer when the methyl group is located on uneven numbered carbons i.e. for the 3-,5- and 7-methyldecanoic acids. (C) 2002 Published by Elsevier Science Ltd.