(R)-1,2-O-isopropylidene glycerol propionate | 62244-19-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-1,2-O-isopropylidene glycerol propionate
• 英文别名: (R)-solketal propionate；(R)-2,2-dimethyl-4-propionyloximethyl-[1,3]dioxolane；(R)-2,2-Dimethyl-4-propionyloxymethyl-[1,3]dioxolan；[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl propanoate
• CAS: 62244-19-3
• 化学式: C₉H₁₆O₄
• 分子量: 188.224
• InChiKey: NGWPJKMXMOMEGH-ZETCQYMHSA-N

物化性质

• 沸点：
  228.3±20.0 °C(Predicted)
• 密度：
  1.026±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 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 、 丙酸 在 4-二甲氨基吡啶 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以79%的产率得到(R)-1,2-O-isopropylidene glycerol propionate
  参考文献：
  名称：

  Lipases Aided Esterification of (2,2-Dimethyl-1,3-dioxolan-4-yl)methanol

  摘要：

  消旋的索克替醛（2,2-二甲基-1,3-二恶烷-4-基）甲醇1，在不同脂肪酶的存在下，与不同链长的羧酸或其乙烯酯反应。酯化反应在正己烷或二异丙基醚中进行。索克替醛酯的产率和它们的手性纯度令人满意，这一点通过使用手性柱的气相色谱法得到了证实。来自米麹霉和荧光假单胞菌的脂肪酶在索克替醛与乙烯丁酸酯在室温下的二异丙基醚溶液中反应时，给出了最佳的对映体过量（ee值）。

  DOI：

  10.2174/157017861101140113155507

文献信息

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

  DOI：——

  日期：——
• Application of pig liver esterase catalyzed transesterification in organic media to the kinetic resolution of glycerol derivatives
  作者：Manfred Jungen、Hans-Joachim Gais

  DOI：10.1016/s0957-4166(99)00380-8

  日期：1999.9

  The PLE/MPEG catalyzed transesterification of the glycerol ketals rac-1a and rac-1d-f with vinyl propionate in toluene proceeded with good selectivities (E=24-34) and gave the enantiomerically enriched S-alcohols 1a and 1d-f, and the S-esters 2a and 2d-f. High selectivities (E=99 and E greater than or equal to 200) were observed in the transesterification of the glycerol ether rac-3 and its desoxy analog rac-5, both having a secondary hydroxy group, with PLE/MPEG. In transesterifications in organic media PLE exhibited a much higher enantioselectivity than in hydrolysis in water. (C) 1999 Elsevier Science Ltd. All rights reserved.
• 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.
• Oligomers of Straight-Chain and Unbranched Fatty Acids and Drugs Containing These
  申请人：Wolf Hans Uwe

  公开号：US20090012166A1

  公开（公告）日：2009-01-08

  The present invention relates to new substances which are derived from naturally occurring straight-chain and unbranched fatty acids and also from semi-synthetic and synthetic compounds with principally the same structure in that they represent dimers, trimers, tetramers or higher oligomers of the starting substances.
• US7964640B2
  申请人：——

  公开号：US7964640B2

  公开（公告）日：2011-06-21