2-tetrahydropyranyl ether of isobutyl alcohol | 32767-69-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 2-tetrahydropyranyl ether of isobutyl alcohol
• 英文别名: sec-butyl tetrahydropyranyl ether；2H-Pyran, tetrahydro-2-(1-methylpropoxy)-；2-butan-2-yloxyoxane
• CAS: 32767-69-4
• 化学式: C₉H₁₈O₂
• 分子量: 158.241
• InChiKey: GKBFTJFDXHMTGZ-UHFFFAOYSA-N

物化性质

• 沸点：
  185.3±8.0 °C(Predicted)
• 密度：
  0.91±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-tetrahydropyranyl ether of isobutyl alcohol 在 磷酸铁(III) 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以90%的产率得到仲丁醇
  参考文献：
  名称：

  Anhydrous FePO4 as a Cost-Effective and Recyclable Catalyst for Tetrahydropyranylation and Tetrahydrofuranylation of Alcohols and Phenols

  摘要：

  本文开发了一种温和且高效的方案，可在室温下利用少量的无水FePO4作为催化剂，在较短的反应时间内，将多种脂肪族和苄基醇以及酚转化为相应的四氢吡喃醚和四氢呋喃醚（使用3,4-二氢-2H-吡喃，DHP和2,3-二氢呋喃，DHF），产率良好至优秀。

  DOI：

  10.2174/157017811796064485
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 、 仲丁醇 在 sulfated ZrO₂ 作用下， 以94%的产率得到2-tetrahydropyranyl ether of isobutyl alcohol
  参考文献：
  名称：

  用于醇和酚的无溶剂四氢吡喃化反应的高效氧化锆催化剂

  摘要：

  摘要醇和酚在硫酸化氧化锆催化剂的存在下以良好到极好的收率在无溶剂条件下被四氢吡喃化。

  DOI：

  10.1081/scc-120014966

文献信息

• Metal Benzenesulfonates/Acetic Acid Mixtures as Novel Catalytic Systems: Application to the Protection of a Hydroxyl Group
  作者：Min Wang、Jingjing Gao、Zhiguo Song

  DOI：10.1515/znb-2010-1109

  日期：2010.11.1

  A surprising synergistic effect has been discovered in mixtures of metal benzenesulfonates (Co, Al, Ni, Zn, Cd, Pr, La, Cu, Mn) and acetic acid, leading to active catalytic systems for the tetrahydropyranylation of alcohols and phenols to produce tetrahydropyranyl ethers. All reactions proceed mildly and efficiently with moderate to high yields at room temperature without solvent. After the reaction, the metal benzenesulfonate can be easily recovered and reused many times. The efficiency of these systems might result from the “double activation” by Brønsted and Lewis acid catalysis.

  在金属苯磺酸盐（Co，Al，Ni，Zn，Cd，Pr，La，Cu，Mn）和乙酸的混合物中发现了令人惊讶的协同效应，导致了活性催化系统的产生，用于将醇和酚四氢吡喃化生成四氢吡喃基醚。所有反应在室温下在无溶剂的条件下温和高效地进行，产率适中至高。反应后，金属苯磺酸盐可以轻松回收并多次重复使用。这些系统的效率可能是由于Brønsted和Lewis酸催化的“双重活化”。
• Solvent-free tetrahydropyranylation of alcohols catalyzed by amine methanesulfonates
  作者：Rui Wang、MingZhu Sun、Heng Jiang

  DOI：10.1007/s11164-010-0222-6

  日期：2011.1

  A comparative study of tetrahydropyranylation of alcohols under various solvents or solvent-free conditions using different amine methanesulfonates as catalysts shows that tetrahydropyranyl ethers of alcohols are obtained under solvent-free conditions in good yields using catalytic amounts of triethylenediamine methanesulfonate, 1,6-hexanediamine methanesulfonate, diethylenetriamine methanesulfonate and pyridine methanesulfonate, respectively. The reaction occurs readily in short times at room temperature catalyzed by these catalysts, especially triethylenediamine methanesulfonate. Some of the major advantages of this procedure are that the catalysts are environmentally friendly, highly effective, and easy to prepare and handle. The reaction is also clean and needs no solvent, and the work-up is very simple.

  不同溶剂或无溶剂条件下使用不同的胺甲磺酸盐作为催化剂对醇的四氢吡喃化反应的比较研究表明，在无溶剂条件下，使用催化量的三亚乙基二胺甲磺酸盐、1,6-己二胺甲磺酸盐、二亚乙基三胺甲磺酸盐和吡啶甲磺酸盐分别能以良好的产率得到醇的四氢吡喃醚。这些催化剂，特别是三亚乙基二胺甲磺酸盐，能够在室温下短时间内催化反应顺利进行。该方法的主要优点是催化剂环境友好、高效且易于制备和处理。反应干净且无需溶剂，后处理非常简单。
• 1,6-HEXANEDIAMINE METHANESULFONATE: A MILD AND EFFICIENT CATALYST FOR THE TETRAHYDROPYRANYLATION OF ALCOHOLS UNDER SOLVENT-FREE CONDITIONS
  作者：Rui Wang、Heng Jiang

  DOI：10.1080/10826068.2010.488491

  日期：2010.7.14

  Various alcohols react with 3,4-dihydro-2 H-pyran under mild conditions using a catalytic amount of 1,6-hexanediamine methanesulfonate. It affords the corresponding tetrahydropyranyl ethers in good yields at a faster rate in the absence of solvent.

  在温和的条件下，使用催化量的1,6-己二胺甲磺酸盐，各种醇与3,4-二氢-2 H-吡喃反应。在不存在溶剂的情况下，它以较快的速率以良好的产率提供了相应的四氢吡喃基醚。
• Copper nitrate/acetic acid as an efficient synergistic catalytic system for the chemoselective tetrahydropyranylation of alcohols and phenols
  作者：Min Wang、Zhi-Guo Song、Hong Gong、Heng Jiang

  DOI：10.1007/s00706-008-0051-0

  日期：2009.2

  ylation of alcohols and phenols was accomplished successfully using copper nitrate and acetic acid as a synergistic catalyst at room temperature under solvent-free condition. Compared with other synergistic catalytic systems, copper nitrate/acetic acid proved to be the most efficient. Both alcohols (primary, secondary, tertiary, benzylic, cyclic, allyl, cinnamyl, and furyl) and phenols reacted smoothly

  摘要使用硝酸铜和乙酸作为增效催化剂，在室温和无溶剂条件下成功完成了醇和酚的四氢吡喃基化反应。与其他协同催化系统相比，硝酸铜/乙酸被证明是最有效的。两种醇（伯，仲，叔，苄基，环状，烯丙基，肉桂基和呋喃基）和酚均能以高收率平稳反应。 图形概要
• Tetrahydropyranylation of Alcohols and Phenols Using the Synergistic Catalyst System, Copper(II) Chloride-Acetic Acid
  作者：Min Wang、Zhi-Guo Song、Heng Jiang、Hong Gong

  DOI：10.1007/s00706-007-0631-4

  日期：2007.6

  Copper(II) chloride-acetic acid was found to be an efficient synergistic catalytic system for the tetraphydropyranylation of various alcohols and phenols in high yields at room temperature in short reaction times.

  发现氯化铜（II）-乙酸是一种高效的协同催化体系，可在室温下以较短的反应时间高收率地对各种醇和酚进行四邻苯二甲酰化。