(3R)-3-methyldecanoic 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: (3R)-3-methyldecanoic acid
• 化学式: C₁₁H₂₂O₂
• 分子量: 186.294
• InChiKey: ZGDHFHMCRRTRAW-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 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

• 作为反应物：
  描述：

  (3R)-3-methyldecanoic acid 在 草酰氯 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成
  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
• 作为产物：
  描述：

  cis-3,4-Methylenedecanoic acid 在 C₃₈H₃₆IrO₂P 、 氢气 、 caesium carbonate 作用下， 以 正丁醇 为溶剂， 65.0 ℃ 、303.99 kPa 条件下， 反应 0.5h， 以99%的产率得到(3R)-3-methyldecanoic acid
  参考文献：
  名称：

  具有手性膦-羧基配体的中性铱催化剂用于不饱和羧酸的不对称氢化†

  摘要：

  我们开发了具有手性螺环膦-羧基配体 (SpiroCAP) 的中性铱催化剂，用于不饱和羧酸的不对称氢化。与阳离子 Crabtree 型催化剂不同，具有手性螺环膦-羧基配体的铱催化剂是中性的，不需要使用四[3,5-双(三氟甲基)苯基]硼酸盐 (BAr F -) 抗衡离子，这是稳定阳离子 Crabtree 型催化剂所必需的。中性铱催化剂的另一个优点是它们具有高稳定性并且在空气中具有长寿命。具有手性螺环膦-羧基配体的新型铱催化剂在各种不饱和羧酸的不对称氢化中表现出前所未有的高对映选择性（高达 99.4% ee），特别是对于 3-烷基-3-亚甲基丙酸而言，这对其他手性的底物具有挑战性催化剂。

  DOI：

  10.1039/c6sc03764j

文献信息

• Neutral iridium catalysts with chiral phosphine-carboxy ligands for asymmetric hydrogenation of unsaturated carboxylic acids
  作者：Shuang Yang、Wen Che、Hui-Ling Wu、Shou-Fei Zhu、Qi-Lin Zhou

  DOI：10.1039/c6sc03764j

  日期：——

  We developed neutral iridium catalysts with chiral spiro phosphine-carboxy ligands (SpiroCAP) for asymmetric hydrogenation of unsaturated carboxylic acids. Different from the cationic Crabtree-type catalysts, the iridium catalysts with chiral spiro phosphine-carboxy ligands are neutral and do not require the use of a tetrakis[3,5-bis(trifluoromethyl)phenyl]borate (BArF−) counterion, which is necessary

  我们开发了具有手性螺环膦-羧基配体 (SpiroCAP) 的中性铱催化剂，用于不饱和羧酸的不对称氢化。与阳离子 Crabtree 型催化剂不同，具有手性螺环膦-羧基配体的铱催化剂是中性的，不需要使用四[3,5-双(三氟甲基)苯基]硼酸盐 (BAr F -) 抗衡离子，这是稳定阳离子 Crabtree 型催化剂所必需的。中性铱催化剂的另一个优点是它们具有高稳定性并且在空气中具有长寿命。具有手性螺环膦-羧基配体的新型铱催化剂在各种不饱和羧酸的不对称氢化中表现出前所未有的高对映选择性（高达 99.4% ee），特别是对于 3-烷基-3-亚甲基丙酸而言，这对其他手性的底物具有挑战性催化剂。
• 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.