2-己氧基丙烷-1,3-二醇 | 10305-38-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 中文名称: 2-己氧基丙烷-1,3-二醇
• 英文名称: hexyl glycerol
• 英文别名: 3-(hexyloxy)propane-1,2-diol；3-n-hexyloxy-1,2-propanediol；3-hexyloxy-1,2-propanediol；1-O-hexyl-glycerol ether；3-hexoxy-1,2-propanediol；hexoxy-propan-1,2-diol；3-hexoxypropane-1,2-diol
• CAS: 10305-38-1
• 化学式: C₉H₂₀O₃
• mdl: MFCD00167017
• 分子量: 176.256
• InChiKey: MQVMITUCTLYRNV-UHFFFAOYSA-N

物化性质

• 沸点：
  278℃ at 102.7-102.9kPa
• 密度：
  0.97g/cm3 at 20℃
• LogP：
  1.81 at 20℃
• 表面张力：
  56.2mN/m at 1g/L and 20℃

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  8
• 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

制备方法与用途

O-己基-rac-甘油是一种生物化学试剂，可用于生物材料或有机化合物的研究，在生命科学领域有着广泛的应用价值。

反应信息

• 作为反应物：
  描述：

  2-己氧基丙烷-1,3-二醇 在 硼酸三乙酯 、 水 、 硼酸 、 sodium hydride 、 三乙胺 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 、 异丙醇 、 甲苯 为溶剂， 反应 22.0h， 生成
  参考文献：
  名称：

  Structure-activity relationship in PAF-acether. 3. Hydrophobic contribution to agonistic activity

  摘要：

  The synthesis of some selected PAF-acether homologues with an alkoxy-chain length from C1 to C20 in position 1 is described. All agonist activities are closely correlated among themselves and with the calculated fatty-chain hydrophobicity. After a discussion on recent published results and comparison with our data, we conclude that the ether oxide function is absolutely essential at the glycerol 1-position for potent agonist activity and that potency correlates well with hydrophobicity parameters. We indicate the importance of steric and configurational constraints.

  DOI：

  10.1021/jm00388a008
• 作为产物：
  描述：

  1-氯-3-(己氧基)-2-丙醇 在 sodium hydroxide 、 高氯酸 作用下， 以 水 为溶剂， 反应 22.0h， 生成 2-己氧基丙烷-1,3-二醇
  参考文献：
  名称：

  Gloe, K.; Muehl, P.; Beger, J., Journal fur praktische Chemie (Leipzig 1954), 1991, vol. 333, # 3, p. 413 - 421

  摘要：

  DOI：

文献信息

• 1-O-Alkyl (di)glycerol ethers synthesis from methyl esters and triglycerides by two pathways: catalytic reductive alkylation and transesterification/reduction
  作者：Marc Sutter、Wissam Dayoub、Estelle Métay、Yann Raoul、Marc Lemaire

  DOI：10.1039/c3gc36907b

  日期：——

  esters, monoglycerides or oleic sunflower refined oil, the corresponding 1-O-alkyl (di)glycerol ethers were obtained in both high yields and selectivity by two different pathways. With methyl esters, a reductive alkylation with (di)glycerol was realized under 50 bar hydrogen pressure in the presence of 1 mol% of Pd/C and an acid co-catalyst. A second two step procedure was evaluated from methyl esters

  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。
• 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。
• 1,2,3-Trimethoxypropane and Glycerol Ethers as Bio-Sourced Solvents from Glycerol. Synthesis by Solvent-Free Phase-Transfer Catalysis and Utilization as an Alternative Solvent in Chemical Transformations
  作者：Marc Sutter、Wissam Dayoub、Estelle Métay、Yann Raoul、Marc Lemaire

  DOI：10.1002/cctc.201300458

  日期：2013.10

  phase‐transfer catalyst with no additional solvent. No heating was required, and the synthesis was easily performed under atmospheric pressure on a 150 g scale. For the preparation of 2, the conversion of glycerol was complete and the selectivity for the expected glycerol trimethylether was above 95 %. This product was utilized as a solvent in organic reactions such as transesterifications between glycerol

  1,2,3-三甲氧基丙烷（2），1-烷氧基-2,3-二甲氧基丙烷和1-芳氧基-2,3-二甲氧基丙烷在固相转移催化中得到了良好的收率和选择性。无机碱和铵盐作为相转移催化剂，无需其他溶剂。不需要加热，并且容易在大气压下以150g规模进行合成。准备2，甘油的转化完成，并且预期的甘油三甲醚的选择性高于95％。该产品在有机反应中用作溶剂，例如甘油和植物油之间的酯交换反应，有机金属反应（格氏和巴比尔型反应），碳-碳偶联反应（Suzuki，Sonogashira，Heck）以及在脱氢反应中的醚化反应中烷基化。溶剂显示出有趣的聚合物增溶性能。
• 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。
• Prodrugs of a 3-(pyrrol-2-ylmethylidene)-2-indolinone derivatives
  申请人：Sugen. Inc.

  公开号：US20030100555A1

  公开（公告）日：2003-05-29

  The present invention relates to pyrrole substituted 2-indolinone compounds and their pharmaceutically acceptable salts which modulate the activity of protein kinases and therefore are expected to be useful in the prevention and treatment of protein kinase related cellular disorders such as cancer.

  本发明涉及吡咯替代的2-吲哚酮化合物及其药学上可接受的盐，这些化合物调节蛋白激酶的活性，因此预计在预防和治疗蛋白激酶相关的细胞疾病，如癌症方面具有用处。