(RS)-1,2-O-异亚丙基甘油对甲氧基苯甲酸酯 | 109368-16-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (RS)-1,2-O-异亚丙基甘油对甲氧基苯甲酸酯
• 英文名称: (2,2-dimethyl-1,3-dioxolane-4-yl)methyl p-methoxybenzoate
• 英文别名: (RS)-1,2-O-isopropylidene glycerol 4-methoxybenzoate；(RS)-1,2-O-isopropylidene glycerol p-methoxybenzoate；(2,2-dimethyl-1,3-dioxolan-4-yl)methyl 4-methoxybenzoate
• CAS: 109368-16-3
• 化学式: C₁₄H₁₈O₅
• 分子量: 266.294
• InChiKey: QUUMCVJKQBLRGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.0
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (RS)-1,2-O-异亚丙基甘油对甲氧基苯甲酸酯 在 Bacillus coagulans NCIMB 9365 dry cells 作用下， 以 水 、 丙酮 为溶剂， 反应 24.0h， 生成 (S)-(+)-1,2-异亚丙基甘油 、 (R)-(-)-甘油醇缩丙酮 、 (S)-1,2-O-isopropylidene glycerol 4-methoxybenzoate 、 (R)-1,2-O-isopropylidene glycerol 4-methoxybenzoate
  参考文献：
  名称：

  Enhanced enantioselectivity of Bacillus coagulans in the hydrolysis of 1,2-O-isopropylidene glycerol esters by thermal knock-out of undesired enzymes

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2004.12.021
• 作为产物：
  描述：

  4-甲氧基苯甲酸酐 、 丙酮缩甘油 在 吡啶 作用下， 以 苯 为溶剂， 生成 (RS)-1,2-O-异亚丙基甘油对甲氧基苯甲酸酯
  参考文献：
  名称：

  Enhanced enantioselectivity of Bacillus coagulans in the hydrolysis of 1,2-O-isopropylidene glycerol esters by thermal knock-out of undesired enzymes

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2004.12.021

文献信息

• 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.