(R)-1,2-O-isopropylidene glycerol hexanoate | 189633-90-7

• 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)-1,2-O-isopropylidene glycerol hexanoate
• 英文别名: (R)-(2,2-dimethyl-1,3-dioxolan-4-yl)methyl hexanoate；(R)-4-hexanoyloximethyl-2,2-dimethyl-[1,3]dioxolane；(R)-4-Hexanoyloxymethyl-2,2-dimethyl-[1,3]dioxolan；[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl hexanoate
• CAS: 189633-90-7
• 化学式: C₁₂H₂₂O₄
• 分子量: 230.304
• InChiKey: KFKXVIFHVSPPFG-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (S)-(+)-1,2-异亚丙基甘油 、 己酰氯 在 吡啶 、 氯仿 作用下， 生成 (R)-1,2-O-isopropylidene glycerol hexanoate
  参考文献：
  名称：

  Baer; Fischer, Journal of the American Chemical Society, 1945, vol. 67, p. 2036

  摘要：

  DOI：

文献信息

• Optically Active Monoacylglycerols: Synthesis and Assessment of Purity
  作者：Chao-Yuan Chen、Wei-Bo Han、Hui-Jun Chen、Yikang Wu、Po Gao

  DOI：10.1002/ejoc.201300247

  日期：2013.7

  Despite their simple structures, synthesis of 1(or 3)-acyl-sn-glycerols remains a challenge that cannot be ignored because of facile acyl migrations, which not only complicate the synthesis but also make direct GC or HPLC analysis unfeasible. Assessment of the optical purity of monoacylglycerols has, to date, relied almost exclusively on specific rotation data, which are small in value and thus insensitive

  尽管结构简单，但 1（或 3）-酰基-sn-甘油的合成仍然是一个不容忽视的挑战，因为酰基迁移容易，这不仅使合成复杂化，而且使直接 GC 或 HPLC 分析不可行。迄今为止，单酰基甘油光学纯度的评估几乎完全依赖于比旋光度数据，这些数据价值小，因此对杂质不敏感。现在，已经找到了一种“放大”小比旋光度的简单方法，以及测量 1,2- 和 1,3-酰基迁移的实用方法，这些方法为 Mori 的 NMR 分析提供了一种方便且直接的替代方法。莫舍酯。借助这些方法，在合成两种天然单酰基甘油的过程中，研究了一系列脱丙酮的条件。
• Kinetics of enzymatic synthesis of isopropylidene glycerol esters by goat pregastric lipase
  作者：Douglas T. Lai、Norikatsu Hattori、Charmian J. O’Connor

  DOI：10.1007/s11746-999-0075-6

  日期：1999.7

  AbstractThe goat pregastric lipase‐catalyzed esterification of isopropylidene glycerol with caproic acid, to form isopropylidene glycerol caproate, followed a ping pong bi bi mechanism incorporating an acyl‐enzyme intermediate. The maximum rate was estimated to be 96 µmol min−1 mg−1 in isooctane at 35°C, and the Michaelis‐Menten constants for isopropylidene glycerol and caproic acid were 0.23 and 0.32 M, respectively. The catalyzed rate also correlated well with the partition coefficient of caproic acid between the organic and aqueous phases. The results suggest that the desolvation energy of the substrate from the bulk medium to the active site of the enzyme dominates the reaction rate for the enzyme‐catalyzed reaction in organic media.
• Enhanced enantioselectivity of Bacillus coagulans in the hydrolysis of 1,2-O-isopropylidene glycerol esters by thermal knock-out of undesired enzymes
  作者：Diego Romano、Francesco Falcioni、Diego Mora、Francesco Molinari、Andreas Buthe、Marion Ansorge-Schumacher

  DOI：10.1016/j.tetasy.2004.12.021

  日期：2005.2

  The enantioselective hydrolysis of different (RS)-1,2-O-isopropylidene glycerol esters has been achieved with whole cells of Bacillus coagulans NCIMB 9365 furnishing the (S)-alcohol as the major enantiomer. The reaction is catalysed by a thermostable cell-bound carboxylesterase and improvement of the enantioselectivity has been achieved by heat treatment of the whole cells, which causes the knock-outs a non-enantioselective competing enzyme. Thermally-treated cells hydrolysed (RS)-1,2-O-isopropylidene glycerol esters with high enantioselectivity, the highest enantiomeric ratio (80-100) being observed for the benzoate. The biocatalyst displayed good stability and could be re-used after filtration for 12 cycles before showing significant loss of activity; repeated biotransformation batches allowed the recovery of 9.55 g/L of enantiomerically pure (S)-isopropylideneglycerol benzoate starting from 24.0 g/L of the racemic mixture. (C) 2005 Elsevier Ltd. All rights reserved.