(+/-)-2-acetoxyhexyl tosylate | 1018979-16-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+/-)-2-acetoxyhexyl tosylate
• 英文别名: 1-(4-Methylphenyl)sulfonyloxyhexan-2-yl acetate
• CAS: 1018979-16-2
• 化学式: C₁₅H₂₂O₅S
• 分子量: 314.403
• InChiKey: NBDSRPXHQLRZLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+/-)-2-acetoxyhexyl tosylate 、 溶剂黄146 在 PS lipase 、 偶氮二甲酸二乙酯 作用下， 以 异丙醚 、 甲苯 为溶剂， 反应 49.0h， 以91%的产率得到(S)-2-acetoxyhexyl tosylate
  参考文献：
  名称：

  Deracemization of 1,2-diol monotosylate derivatives by a combination of enzymatic hydrolysis with the Mitsunobu inversion using polymer-bound triphenylphosphine

  摘要：

  The deracemization of 1,2-diol monotosylate derivatives is achieved by the sequential combination of enzymatic hydrolysis and Mitsunobu inversion using a polymer-bound triphenylphosphine. After the lipase-catalysed hydrolysis of the racemic 2-acetoxyhexyl tosylate, the subsequent Mitsunobu reaction without separation causes an inversion of the resulting (R)-alcohol to give the (S)-enantiomer of the acetate as a single product. In particular, the reaction using the polymer-bound triphenylphosphine also proceeds smoothly, and the product is easily separated by filtration from the polymer-bound reagent and its by-products. This deracemization process is applicable to the preparation of several optically active 1,2-diol monotosylates. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.11.005
• 作为产物：
  描述：

  乙酸酐 、 甲苯-4-磺酸(2-羟基己基)酯 在 吡啶 作用下， 生成 (+/-)-2-acetoxyhexyl tosylate
  参考文献：
  名称：

  酶水解制备光学活性 1,2-二醇单甲苯磺酸酯

  摘要：

  公开了通过酶促水解容易制备光学活性的1,2-二醇单甲苯磺酸酯衍生物。脂肪酶 PS (BURKHOLDERIA CEPACIA) 以优异的对映选择性催化外消旋甲苯磺酸 2-乙酰氧基己酯的水解，以提供相应的旋光化合物。在该反应中，观察到独特的温度效应。优化反应条件后，该方法可广泛应用于各种高ee光学活性化合物的两种对映体的实际制备。

  DOI：

  10.1055/s-2008-1032047

文献信息

• Immobilization of lipase from Burkholderia cepacia into calcium carbonate microcapsule and its use for enzymatic reactions in organic and aqueous media
  作者：Masahiro Fujiwara、Kumi Shiokawa、Koji Yotsuya、Kazutsugu Matsumoto

  DOI：10.1016/j.molcatb.2014.08.009

  日期：2014.11

  We disclosed a useful procedure for the immobilization of a lipase from Burkholderia cepacia based on its encapsulation into vaterite calcium carbonate microcapsule. The immobilized enzyme had an adequate activity for the hydrolysis of 4-nitrophenyl acetate, which was preserved over 2 years in storage at 4 degrees C. The enantioselective esterification of (+/-)-1-phenylethanol with vinyl acetate using the immobilized lipase smoothly progressed to afford the corresponding optically active compounds, where the enzyme was easily recovered for reuse. Although the hydrolysis of (+/-)-2-acetoxyhexyl tosylate in aqueous solution was catalyzed by the enzyme, the phase transition of calcium carbonate from vaterite to poorly porous calcite during the reaction prevented the access of the reactant to the active site of the lipase, resulting in the significant decrease of the activity of the recovered enzyme. However, the treatment of the immobilized enzyme with zinc chloride solution inhibited the phase transition under the reaction conditions. The enzyme after the zinc treatment was recyclable for the hydrolysis of the substrate without significant decrease of the reactivity even after the uses in aqueous media. (C) 2014 Elsevier B.V. All rights reserved.