1-(tetrahydrofuran-2-yl)ethanol | 16765-41-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: 1-(tetrahydrofuran-2-yl)ethanol
• 英文别名: (RS)-1-(RS)-tetrahydrofuran-2-yl-ethanol；(+/-)-threo-1--aethanol-(1)；(R)-1-((R)-tetrahydrofuran-2-yl)ethanol；(1S)-1-[(2S)-oxolan-2-yl]ethanol
• CAS: 16765-41-6
• 化学式: C₆H₁₂O₂
• 分子量: 116.16
• InChiKey: FGNVEEOZAACRKW-WDSKDSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(tetrahydrofuran-2-yl)ethanol 生成 (2R,3R)-2,3-hexanediol
  参考文献：
  名称：

  Gagnaire,D.; Leclercq,M., Bulletin de la Societe Chimique de France, 1963, p. 721 - 726

  摘要：

  DOI：
• 作为产物：
  描述：

  hept-5-en-1-ol 在 poly(N-isopropylacrylamide)-based phosphotungstate complex 双氧水 作用下， 以 水 为溶剂， 反应 6.0h， 以85%的产率得到1-(tetrahydrofuran-2-yl)ethanol
  参考文献：
  名称：

  利用温度响应催化剂的新型固相反应系统：过氧化氢的氧化环化

  摘要：

  基于温度变化的可转换催化剂在水中提供了一种新颖的固相反应系统。在较高温度下，对有机底物的催化剂亲和力的增加导致有效的活性驱动了固态内相反应，而在较低温度下亲和力的丧失使反应完成时有机产物易于分离。利用该催化剂智能设计新颖的催化系统，可利用过氧化氢进行有效的氧化环化反应，这是一种利用氧杂环的有效方法。

  DOI：

  10.1002/adsc.200700114

文献信息

• Ring Opening of Epoxides by Pendant Silanols
  作者：Someshwar Nagamalla、Joel T. Mague、Shyam Sathyamoorthi

  DOI：10.1021/acs.orglett.1c04310

  日期：2022.1.28

  We present a new ring-opening reaction of epoxides by pendant silanols, catalyzed by either Ph3C+BF4– or BINOL-phosphoric acid. Silanol epoxides derived from trans-allylic alcohols, cis-allylic alcohols, trans-homoallylic alcohols, and cis-homoallylic alcohols were all compatible and gave products from either endo- or exo-ring opening. With silanol epoxides derived from 4-alkenyl silanols, an unusual

  我们提出了一种新的环氧化物开环反应，该反应由侧链硅烷醇进行，由 Ph 3 C + BF 4 –或 BINOL-磷酸催化。衍生自反式烯丙醇、顺式烯丙醇、反式高烯丙醇和顺式高烯丙醇的硅烷醇环氧化物都是相容的，并且可以从内环或外环开环得到产物。对于衍生自 4-烯基硅烷醇的硅烷醇环氧化物，观察到不寻常的重排形成四氢呋喃产物。该方法的实用性在受保护的d-阿拉伯糖醇的简短制备中得到了证明。
• Oxidative cyclization of alkenols with Oxone using a miniflow reactor
  作者：Yoichi M A Yamada、Kaoru Torii、Yasuhiro Uozumi

  DOI：10.3762/bjoc.5.18

  日期：——

  A miniflow system for oxidative cyclization of alkenols with Oxone was developed. Thus, the oxidative cyclization of (Z)- and (E)-alkenols in i-PrOH with an aqueous solution of Oxone proceeded smoothly and safely in a PTFE tube without any exogenous catalytic species, and was subsequently quenched in a flow-reaction manner to afford the corresponding furanyl and pyranyl carbinols quantitatively within 5 or 10 min of residence time.

  开发了一种使用Oxone进行烯醇氧化环化的小流量系统。因此，(Z)-和(E)-烯醇在-PrOH中与Oxone的水溶液在PTFE管中顺利、安全地进行氧化环化，无需任何外源催化物，并随后以流动反应方式迅速熄灭，在5或10分钟的停留时间内定量地得到相应的呋喃基和吡喃基羟基化合物。
• Hot Water-Promoted Ring-Opening of Epoxides and Aziridines by Water and Other Nucleopliles
  作者：Zhi Wang、Yong-Tao Cui、Zhao-Bing Xu、Jin Qu

  DOI：10.1021/jo702401t

  日期：2008.3.1

  Effective hydrolysis of epoxides and aziridines was conducted by heating them in water at 60 or 100 degrees C. Other types of nucleophile such as amines, sodium azide, and thiophenol could also efficiently open epoxides and aziridines in hot water. It was proposed that hot water acted as a modest acid catalyst, reactant, and solvent in the hydrolysis reactions.
• Dihydro- and Tetrahydrofuran Building Blocks from 1,4:3,6-Dianhydrohexitols. 2. Synthesis of Acetal, Alcohol, Diol, Epoxide, Hydrocarbon, and Lactone Pheromones
  作者：Claudio Paolucci、Claudio Mazzini、Antonino Fava

  DOI：10.1021/jo00106a030

  日期：1995.1

  The potential of building blocks 1-3 for synthesis of enantiopure substances is illustrated by their transformation to various insect pheromones featuring functionalities specified in the title. A convenient synthesis of building block 3 from sorbitol is described.
• Tightly Convoluted Polymeric Phosphotungstate Catalyst:  An Oxidative Cyclization of Alkenols and Alkenoic Acids
  作者：Yoichi M. A. Yamada、Haiqing Guo、Yasuhiro Uozumi

  DOI：10.1021/ol070258v

  日期：2007.4.1

  A tightly convoluted polymeric phosphotungstate catalyst was prepared via ionic assembly of H3PW12O40 and poly(alkylpyridinium). An oxidative cyclization of various alkenols and alkenoic acids was efficiently promoted by the polymeric catalyst in aq H2O2 in the absence of organic solvents to afford the corresponding cyclic ethers and lactones in high yield. The catalyst was reused four times without loss of catalytic activity.