(R)-2-octyl laurate | 127307-03-3

• 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: (R)-2-octyl laurate
• 英文别名: [(2R)-octan-2-yl] dodecanoate
• CAS: 127307-03-3
• 化学式: C₂₀H₄₀O₂
• 分子量: 312.536
• InChiKey: MIEBBHYETAOCSS-LJQANCHMSA-N

物化性质

• 沸点：
  354.6±10.0 °C(Predicted)
• 密度：
  0.862±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  22
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  月桂酸 、 仲辛醇 在 lipase-lipide 作用下， 以 异辛烷 为溶剂， 生成 (S)-(+)-2-辛醇 、 (R)-2-octyl laurate
  参考文献：
  名称：

  脂肪酶-脂质复合物作为有机溶剂中外消旋醇的拆分催化剂

  摘要：

  新制备了脂质包覆的脂肪酶，并在无水和均相有机溶剂中大力催化外消旋醇的对映选择性酯化（拆分）反应。

  DOI：

  10.1016/s0040-4039(00)80700-5

文献信息

• Continuous Flow Enzymatic Kinetic Resolution and Enantiomer Separation using Ionic Liquid/Supercritical Carbon Dioxide Media
  作者：Manfred T. Reetz、Wolfgang Wiesenhöfer、Giancarlo Franciò、Walter Leitner

  DOI：10.1002/adsc.200303109

  日期：2003.11

  using various modifications of the lipase from Candida antarctica (CaL-B) in imidazolium-based ionic liquids. The anion of the ionic liquid has a significant influence on the performance of the bio-catalyst with bis(trifluoromethanesulfonamide) [BTA] giving the best results. The acetates 4a–e can be extracted from the reaction mixture preferentially over the alcohols 1a–e with scCO2 under certain conditions

  离子液体（IL）中的动力学拆分和超临界二氧化碳（scCO 2）的选择性萃取相结合，为分离对映异构体提供了一种新方法，以脂肪酶催化的手性仲醇酯化为例。醇1a–e转化为相应的乙酸盐4a–e或月桂酸酯5a–e时，可以使用来自南极假丝酵母的脂肪酶（CaL-B）在咪唑鎓类离子液体中进行多种修饰，从而实现出色的对映选择性。离子液体的阴离子对具有最佳结果的双（三氟甲磺酰胺）[BTA]的生物催化剂的性能有重大影响。醋酸盐4a–e在某些条件下，可以优先从具有scCO 2的醇1a–e中从反应混合物中萃取，但制备上有用的选择性将需要先进的多步萃取程序。相反，如果优先从相应的月桂酸酯5a-e中提取醇1a-e，则可以使用相对简单的设备进行有效分离。基于这些发现，设计了一种不使用有机溶剂即可拆分外消旋醇的“绿色”连续方法。
• Lipase-lipid complex as a resolution catalyst of racemic alcohols in organic solvents
  作者：Yoshio Okahata、Yoshitaka Fujimoto、Kuniharu Ijiro

  DOI：10.1016/s0040-4039(00)80700-5

  日期：1988.1

  A lipid-coated lipase was newly prepared and vigorously catalyzed the reaction of enantioselective esterification (resolution) of racemic alcohols in anhydrous and homogeneous organic solvents.

  新制备了脂质包覆的脂肪酶，并在无水和均相有机溶剂中大力催化外消旋醇的对映选择性酯化（拆分）反应。
• Enzyme reactions in apolar solvents. The resolution of branched and unbranched 2-alkanols by porcine pancreatic lipase.
  作者：Brian Morgani、Allan C. Oehlschlager、Thomas M. Stokes

  DOI：10.1016/s0040-4020(01)96905-4

  日期：1991.1

  Straight-chain and branched 2-alkanols were subjected to enzyme catalyzed transesterification in organic solvent using porcine pancreatic lipase, high enantioselectivity being generally observed. The method was applied to the synthesis of (R)-(-)-9-hydroxy-(E)-decenoic acid, a component of the queen bee mandibular gland pheromone.
• A green resolution–separation process for aliphatic secondary alcohols
  作者：Liwei Ren、Tian Xu、Ruoping He、Zhenhua Jiang、Hua Zhou、Ping Wei

  DOI：10.1016/j.tetasy.2013.01.018

  日期：2013.3

  In order to obtain both enantiomers of aliphatic secondary alcohols via a greener method, the four-step resolution-separation process involving lipase-catalyzed enantioselective esterification and hydrolysis as well as two separation procedures both via heterogeneous azeotropic distillation was developed. (S)-2-Pentanol (ee = 98.6%), (R)-2-pentanol (ee >99%), (S)-2-octanol (ee = 98.2%), and (R)-2-octanol (ee = 98.5%) were all produced in high purity (>98%) and high yield (>90%). In addition to the two model substrates, this method could also be applied to the resolution of other aliphatic secondary alcohols. (C) 2013 Elsevier Ltd. All rights reserved.