2-O-pentylglycerol monoether | 100078-37-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 2-O-pentylglycerol monoether
• 英文别名: 2-monopentyl glycerol；2-(pentyloxy)-1,3-propanediol；2-Pentoxypropane-1,3-diol
• CAS: 100078-37-3
• 化学式: C₈H₁₈O₃
• 分子量: 162.229
• InChiKey: ZQZTVETVPBHROI-UHFFFAOYSA-N

物化性质

• 沸点：
  276.5±20.0 °C(Predicted)
• 密度：
  0.999±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  戊酸甲酯 在 5%-palladium/activated carbon 、 氢气 作用下， 100.0~120.0 ℃ 、5.0 MPa 条件下， 反应 32.0h， 生成 3-戊基氧基丙烷-1,2-二醇 、 2-O-pentylglycerol monoether
  参考文献：
  名称：

  1- ø -烷基（二）甘油醚的合成从甲基酯和甘油三酸酯 通过两种途径：催化还原 烷基化 和酯交换/还原

  摘要：

  从可用的和生物来源的甲酯中， 甘油单酸酯或油酸向日葵精制油，通过两种不同途径以高收率和选择性获得了相应的1- O-烷基（二）甘油醚。对于甲酯，在1mol％的Pd / C和酸助催化剂的存在下，在50巴的氢气压力下，实现了与（二）甘油的还原性烷基化。从甲酯或三油精 包括第一次酯交换反应成相应的 甘油单酸酯与BaO / Al 2 O 3 催化剂，然后 减少在H 2压力下，用可循环利用的非均相催化体系Pd / C和Amberlyst 35合成所需的甘油单醚。另外，还提出了反应机理。

  DOI：

  10.1039/c3gc36907b

文献信息

• POLYOL ETHERS AND PROCESS FOR MAKING THEM
  申请人：Tulchinsky Michael L.

  公开号：US20100048940A1

  公开（公告）日：2010-02-25

  New polyol ether compounds and a process for their preparation. The process comprises reacting a polyol, a carbonyl compound, and hydrogen in the presence of hydrogenation catalyst, to provide the polyol ether. The molar ratio of polyol to carbonyl compound in the process is greater than 5:1.

  新的聚醚醇化合物及其制备方法。该方法包括在氢化催化剂存在下，使聚醇、羰基化合物和氢发生反应，从而提供聚醚醇。在该过程中，聚醇与羰基化合物的摩尔比大于5:1。
• Catalytic etherification of glycerol with short chain alkyl alcohols in the presence of Lewis acids
  作者：Fei Liu、Karine De Oliveira Vigier、Marc Pera-Titus、Yannick Pouilloux、Jean-Marc Clacens、Floryan Decampo、François Jérôme

  DOI：10.1039/c3gc36944g

  日期：——

  Here we report the homogeneously-catalyzed etherification of glycerol with short chain alkyl alcohols. Among the large variety of Brønsted and Lewis acids tested, we show here that metal triflates are not only the most active but are also capable of catalyzing this reaction with an unprecedented selectivity. In particular, in the presence of Bi(OTf)3, the targeted monoalkylglyceryl ethers were obtained with up to 70% yield. Although tested Brønsted acids were also capable of catalyzing the etherification of glycerol with alkyl alcohols, they were found however less active and less selective than Bi(OTf)3. By means of counter experiments, we highlighted that the high activity and selectivity of Bi(OTf)3 may rely on a synergistic effect between Bi(OTf)3 and triflic acid, a Brønsted acid that can be released by in situ glycerolysis of Bi(OTf)3. The scope of this methodology was also extended to other polyols and, in all cases, the monoalkylpolyol ethers were conveniently obtained with fair to good yields.

  我们报道了甘油与短链烷基醇在均相催化下的醚化反应。在测试了大量布朗斯特和路易斯酸后，我们发现金属三氟甲磺酸盐不仅是最活跃的催化剂，而且还能以前所未有的选择性催化这一反应。特别是，在Bi(OTf)3的存在下，目标单烷基甘油醚的产率高达70%。尽管测试的布朗斯特酸也能催化甘油与烷基醇的醚化反应，但它们的活性和选择性都低于Bi(OTf)3。通过对比实验，我们强调Bi(OTf)3的高活性和选择性可能依赖于Bi(OTf)3和三氟甲磺酸（一种可由Bi(OTf)3现场甘油分解释放的布朗斯特酸）之间的协同效应。这种方法的应用范围也扩展到其他多元醇，并且在所有情况下，单烷基多元醇醚都能以合理至良好的产率方便地获得。
• Selective Synthesis of 1-<i>O</i>-Alkyl(poly)glycerol Ethers by Catalytic Reductive Alkylation of Carboxylic Acids with a Recyclable Catalytic System
  作者：Marc Sutter、Wissam Dayoub、Estelle Métay、Yann Raoul、Marc Lemaire

  DOI：10.1002/cssc.201200447

  日期：2012.12

  (Poly)glycerol monoethers were synthesized in good yield and selectivity by the catalytic reductive alkylation of glycerol, diglycerol, and triglycerol with readily available, cheap and/or bio‐sourced carboxylic acids. The reaction was catalyzed by 1 mol % of Pd/C under 50 bar H2 using an acid ion‐exchange resin as a recyclable cocatalyst. The catalytic system was recycled several times, and a mechanism

  （聚）甘油单醚是通过甘油，二甘油和三甘油与现成的廉价和/或生物来源的羧酸的催化还原烷基化反应而合成的，具有良好的收率和选择性。使用酸性离子交换树脂作为可循环助催化剂，在50 bar H 2下以1 mol％的Pd / C催化反应。催化系统被回收了几次，并提出了这种转化的机理。
• Synthesis of Monoalkyl Glyceryl Ethers by Ring Opening of Glycidol with Alcohols in the Presence of Lewis Acids
  作者：Raffaele Cucciniello、Maria Ricciardi、Rosa Vitiello、Martino Di Serio、Antonio Proto、Carmine Capacchione

  DOI：10.1002/cssc.201600989

  日期：2016.12.8

  deals with the production of monoalkyl glyceryl ethers (MAGEs) through a new reaction pathway based on the reaction of glycidol and alcohols catalyzed by Lewis acid‐based catalysts. Glycidol is quantitatively converted with high selectivity (99 %) into MAGEs under very mild reaction conditions (80 °C and 0.01 mol % catalyst loading) in only 1 h using Al(OTf)3 or Bi(OTf)3 as catalyst. The proposed method

  目前的工作涉及通过路易斯酸基催化剂催化的缩水甘油和醇类反应的新反应途径，通过单反应生成甘油单烷基甘油醚（MAGEs）。使用Al（OTf）3或Bi（OTf）3作为催化剂，在非常温和的反应条件（80°C和0.01 mol％的催化剂负载量）下，仅1小时即可将缩水甘油以高选择性（99％）定量转化为MAGEs 。所提出的方法为生产增值产品（例如MAGE）增加了可能的绿色合成方法的选择。
• Regioselective Ring‐Opening of Glycidol to Monoalkyl Glyceryl Ethers Promoted by an [OSSO]‐Fe ^III Triflate Complex
  作者：Francesco Della Monica、Maria Ricciardi、Antonio Proto、Raffaele Cucciniello、Carmine Capacchione

  DOI：10.1002/cssc.201901329

  日期：2019.8.8

  bis‐thioether‐di‐phenolate [OSSO]‐type ligand, was discovered to promote the ring‐opening of glycidol with alcohols under mild reaction conditions (0.05 mol % catalyst and 80 °C). The reaction proceeded with high activity (initial turnover frequency of 1680 h−1 for EtOH) and selectivity (>95 %) toward the formation of twelve monoalkyl glyceryl ethers (MAGEs) in a regioselective fashion (84–96 % yield of the non‐symmetric

  发现具有三硫醚醚-二酚盐[OSSO]型配体的三价铁三价铁配合物可在温和的反应条件（0.05 mol％催化剂和80°C）下促进缩水甘油与醇的开环。反应以高活性（EtOH的初始周转频率为1680 h -1）进行，并以区域选择性方式（十二烷基单烷基甘油醚（MAGEs）形成）的选择性（> 95％）（非-的收率为84–96％）对称区域异构体）。这种合成方法可通过使用富含地壳的金属基催化剂将甘油衍生的平台分子（即缩水甘油）转化为高附加值的产品。