(2,2-dimethyl-1,3-dioxolane-4-yl)methyl caproate | 20620-19-3

• 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: (2,2-dimethyl-1,3-dioxolane-4-yl)methyl caproate
• 英文别名: (RS)-1,2-O-isopropylidene glycerol hexanoate；solketal hexanoate；(+/-)-4-hexanoyloxymethyl-2,2-dimethyl-[1,3]dioxolane；(+/-)-4-Hexanoyloxymethyl-2,2-dimethyl-[1,3]dioxolan；2,3-(Dimethylmethyldioxy)propyl-capronat；(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl hexanoate
• CAS: 20620-19-3
• 化学式: C₁₂H₂₂O₄
• 分子量: 230.304
• InChiKey: KFKXVIFHVSPPFG-UHFFFAOYSA-N

物化性质

• 沸点：
  284.2±20.0 °C(Predicted)
• 密度：
  0.989±0.06 g/cm3(Predicted)

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

• 作为反应物：
  描述：

  (2,2-dimethyl-1,3-dioxolane-4-yl)methyl caproate 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 15.0h， 生成 (S)-1,2-O-isopropylidene glycerol hexanoate
  参考文献：
  名称：

  光学活性单酰基甘油：合成和纯度评估

  摘要：

  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。

  DOI：

  10.1002/ejoc.201300247
• 作为产物：
  描述：

  [2-hydroxy-3-(2-methoxypropan-2-yloxy)propyl] hexanoate 生成 (2,2-dimethyl-1,3-dioxolane-4-yl)methyl caproate
  参考文献：
  名称：

  DAWE, R. D.;WRIGHT, J. L. C., LIPIDS, 23,(1988) N 4, 355-358

  摘要：

  DOI：

文献信息

• Study of the Effect of DATEM. 1. Influence of Fatty Acid Chain Length on Rheology and Baking
  作者：Peter Köhler、Werner Grosch

  DOI：10.1021/jf980891i

  日期：1999.5.1

  To answer the question of which fatty acid residue is the most effective, diacetyltartaric esters of monoglycerides (DATEMs) with fatty acids of chain lengths 6:0-20:0 were synthesized. The activity of synthesized DATEMs and commercial DATEM products was studied by means of rheological methods and a microscale baking test with 10 g of flour. Variation of the acyl residue from 6:0 to 22:0 showed that stearic acid (18:0) had the best effect on the baking activity of DATEM (loaf volume increased by 62%). DATEMs containing unsaturated fatty acids (18:1, 18:2) or DATEMs produced from diacylglycerols instead of monoacylglycerols showed a slight increase of the loaf volumes. A slight effect of DATEM on the rheology of dough was observed. However, much greater was the effect on the gluten isolated from doughs prepared with DATEM. The resistance of gluten to extension was increased after the addition of increasing amounts of DATEM (0.1-0.5%). Within the series of DATEMs derived from the homologous series of monoacylglycerols the product based on glycerol monostearate (18:0) showed a maximum increase of the gluten resistance.
• Lipase-mediated desymmetrization of glycerol with aromatic and aliphatic anhydrides
  作者：Daniela I. Batovska、Shuichirou Tsubota、Yasuo Kato、Yasuhisa Asano、Makoto Ubukata

  DOI：10.1016/j.tetasy.2004.09.033

  日期：2004.11

  Chirazyme L-2 (Candida antarctica) catalyzed esterification of glycerol with aromatic and aliphatic anhydrides in 1,4-dioxane is described. All the aromatic monoacylglycerols (MAGs) were produced as (R)-enantiomers, while aliphatic MAGs were obtained either as racemic mixtures or the (S)-enantiomers. The influence of substituted aromatic rings, chain length, and presence of a conjugated double bond in the acyl donor moiety on the enantiotopic selectivity as well as the efficiency of the enzyme was studied. (C) 2004 Elsevier Ltd. All rights reserved.
• Optimized double kinetic resolution for the preparation of (S)-solketal
  作者：Eero Vänttinen、Liisa T Kanerva

  DOI：10.1016/s0957-4166(97)00057-8

  日期：1997.3

  The lipase AK (lipase from Pseudomonas sp.)-catalysed alcoholysis of racemic solketal (2,2-dimethyl-1,3-dioxolane-4-methanol) esters and acylation of solketal in organic solvents proceeded with E=20-25. This enabled the preparation of the more reactive (S)-enantiomer with more than 30% total isolated yield (based on the racemate) and 95% ee by a double kinetic resolution strategy consisting of enzymatic acylation-chemical saponification-enzymatic acylation or enzymatic alcoholysis-enzymatic acylation sequences. Numerical calculations and theoretical plots for the optimal termination conversions for the 1st and 2nd resolution steps as well as for the final yields as the function of E is considered. (C) 1997 Elsevier Science Ltd.
• 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.
• Hartman, Journal of the Chemical Society, 1959, p. 4134
  作者：Hartman

  DOI：——

  日期：——