furan-2-ol | 22125-63-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: furan-2-ol
• 英文别名: furaneol；2-furanol；hydroxyfuran
• CAS: 22125-63-9
• 化学式: C₄H₄O₂
• 分子量: 84.0746
• InChiKey: ICGWWCLWBPLPDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  33.4
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2932190090

反应信息

• 作为反应物：
  描述：

  furan-2-ol 在 hemicucurbit[6]uril 作用下， 以 重水 为溶剂， 生成 呋喃-2,5-二醇
  参考文献：
  名称：

  Hemicucurbit[6]uril-induced aerobic oxidation of heterocyclic compounds

  摘要：

  The aerobic oxidation of furan in aqueous solution in the presence of HemiQ[16] has been investigated, and the product furan-2,5-diol is stabilized by encapsulation of HemiQ[16], which could be transformed to the dione confirmation in acidic solution and escape from the macrocyclic compound. The H-1 NMR titration experiments of the host-guest interaction at different pH values suggest protonation should improve the encapsulation, and therefore an unique property that HemiQI6] can be protonated has been revealed. The oxidizing kinetics suggests that the procedure is a consecutive reaction with a series of constants k(1) =2.9 x 10(-2) min(-1) , k(2) = 2.7 x 10(-2) min(-1), and k(3) = 5.7 x 10(-3) min(-1), respectively. The kinetic investigation at pD =2.0 indicates the HemiQ[6]-catalytic oxidation of furan could be accelerated by acidification. As a consequence, a plausible mechanism has been established on the above evidences. 2-Methylfuran is employed to give the product 2-methylfuran-5-ol exhibiting a satisfied activity in this aerobic oxidation with the supramolecular catalysis of HemiQ[6], but the oxidation of thiophene is very slow in either neutral or acidic condition. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2013.08.025
• 作为产物：
  描述：

  呋喃 在 hemicucurbit[6]uril 作用下， 以 重水 为溶剂， 生成 furan-2-ol
  参考文献：
  名称：

  Hemicucurbit[6]uril-induced aerobic oxidation of heterocyclic compounds

  摘要：

  The aerobic oxidation of furan in aqueous solution in the presence of HemiQ[16] has been investigated, and the product furan-2,5-diol is stabilized by encapsulation of HemiQ[16], which could be transformed to the dione confirmation in acidic solution and escape from the macrocyclic compound. The H-1 NMR titration experiments of the host-guest interaction at different pH values suggest protonation should improve the encapsulation, and therefore an unique property that HemiQI6] can be protonated has been revealed. The oxidizing kinetics suggests that the procedure is a consecutive reaction with a series of constants k(1) =2.9 x 10(-2) min(-1) , k(2) = 2.7 x 10(-2) min(-1), and k(3) = 5.7 x 10(-3) min(-1), respectively. The kinetic investigation at pD =2.0 indicates the HemiQ[6]-catalytic oxidation of furan could be accelerated by acidification. As a consequence, a plausible mechanism has been established on the above evidences. 2-Methylfuran is employed to give the product 2-methylfuran-5-ol exhibiting a satisfied activity in this aerobic oxidation with the supramolecular catalysis of HemiQ[6], but the oxidation of thiophene is very slow in either neutral or acidic condition. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2013.08.025

文献信息

• Nickel-catalyzed cyanation of phenol derivatives activated by 2,4,6-trichloro-1,3,5-triazine
  作者：Liang Wang、Yaoyao Wang、Jun Shen、Qun Chen、Ming-Yang He

  DOI：10.1039/c8ob01034j

  日期：——

  A nickel-catalyzed cyanation of phenol derivatives activated by 2,4,6-trichloro-1,3,5-triazine (TCT) using aminoacetonitrile as the cyanating agent is described. This catalytic system delivered the desired products in moderate to good yields with good substrate compatibility. The readily available starting materials, cost-effective nickel catalyst and metal-free cyanating agent are the major features

  描述了使用氨基乙腈作为氰化剂的被2,4,6-三氯-1,3,5-三嗪（TCT）活化的苯酚衍生物的镍催化氰化反应。该催化体系以中等至良好的产率提供了所需的产物，并具有良好的底物相容性。容易获得的原料，具有成本效益的镍催化剂和不含金属的氰化剂是本方法的主要特征。
• Mukaiyama-Michael Reactions with<i>trans</i>-2,5-Diarylpyrrolidine Catalysts: Enantioselectivity Arises from Attractive Noncovalent Interactions, Not from Steric Hindrance
  作者：Eeva K. Kemppainen、Gokarneswar Sahoo、Antti Piisola、Andrea Hamza、Bianka Kótai、Imre Pápai、Petri M. Pihko

  DOI：10.1002/chem.201304240

  日期：2014.5.12

  the predicted and observed stereoselectivities. The analysis of intermolecular forces reveals that the enantioselectivity is mostly due to stabilizing noncovalent interactions between the reacting partners, not due to steric hindrance. The role of attractive noncovalent interactions in enantioselective catalysis may be underappreciated.

  反式2,5-二苯基吡咯烷催化的对映选择性Mukaiyama-Michael反应的范围已扩大到包括α-和β-取代的Enals。但是，由于催化剂的空间位阻不是很强，因此观察到的对映选择性的合理化还远远不够。进行DFT计算以合理化观察到的立体选择性。作为C过渡态定位亚胺中间体和甲硅烷氧基呋喃之间的C键形成，并用它们的相对能量估算立体选择性数据。我们在预测和观察到的立体选择性之间发现了极好的一致性。分子间力的分析表明，对映选择性主要是由于稳定了反应伙伴之间的非共价相互作用，而不是由于空间位阻。有吸引力的非共价相互作用在对映选择性催化中的作用可能未被充分认识。
• Novel CuCl2-cryptand-[2.2.Benzo] complex: A base free and oxidant free catalyst for Ipso-Hydroxylation of aryl/heteroaryl-boronic acids in water at room temperature
  作者：Sankar Jyoti Bora、Bolin Chetia

  DOI：10.1016/j.jorganchem.2017.09.011

  日期：2017.11

  A novel cryptand and its copper complex was synthesised, which found to have enormous catalytic activity towards ipso-hydroxylation of aryl or heteroarylboronic acids and esters in water without using H2O2 or other oxidising agent and base at room temperature. This newly developed method efficiently converts aryl boronic acids and esters as well as heteroaryl boronic acids to their corresponding phenols

  合成了一种新型的穴状体及其铜配合物，发现其在室温下对水中的芳基或杂芳基硼酸和酯的ipso-羟基化具有巨大的催化活性，而无需使用H 2 O 2或其他氧化剂和碱。这种新开发的方法可在很短的反应时间内以高收率高效地将芳基硼酸和酯以及杂芳基硼酸转化为相应的苯酚。已经发现该协议与各种各样的功能组完全匹配。该方法的优点是高收率，非常短的反应时间，易于分离，可重复使用至第6次。
• An efficient base and H₂O₂ free protocol for the synthesis of phenols in water and oxygen using spinel CuFe₂O₄ magnetic nanoparticles
  作者：Rituparna Chutia、Bolin Chetia

  DOI：10.1080/00958972.2020.1802437

  日期：2020.7.2

  Abstract An efficient base and H2O2 free protocol was used for the synthesis of phenols from boronic acids using biogenic CuFe2O4 magnetic nanoparticles as catalyst at room temperature in water and oxygen. The catalyst was prepared using the flowers of Lantana camara. The size of the nanoparticles was 4.27 nm. Base free and ligand free protocol, less time, excellent yields, room temperature, biogenic

  摘要 使用生物源性 CuFe2O4 磁性纳米粒子作为催化剂，在室温下在水和氧气中，使用一种有效的无碱和 H2O2 协议从硼酸合成酚。催化剂是用马缨丹花制备的。纳米颗粒的尺寸为 4.27 nm。无碱和无配体协议、时间短、产率高、室温、催化剂的生物合成、使用 O2 作为环境友好型氧化剂是本协议的优点。催化剂的可回收性为 5 个循环，磁性或催化活性没有损失。
• A simple, fast and excellent protocol for the synthesis of phenols using $$\hbox {CuFe}_{2}\hbox {O}_{4}$$ magnetic nanoparticles
  作者：Rituparna Chutia、Bolin Chetia

  DOI：10.1007/s12039-019-1624-7

  日期：2019.6

  Heterogeneous catalyst, easy recyclability, mild reaction conditions, short reaction time added as an advantage for the present protocol. Graphical AbstractA very mild, quick and efficient protocol has been designed for the preparation of phenols from phenyl boronic acids using \(\hbox CuFe}_2}\hbox O}_4}\) Magnetic Nanoparticles (MNPs) as a catalyst. Heterogeneous catalyst, easy recyclability added as

  摘要本文描述了使用\（\ hbox CuFe} _ 2} \ hbox O} _ 4} \）磁性纳米粒子作为催化剂合成酚的非常温和，快速且简单的方案。纳米催化剂的平均直径为17.63nm。通过SEM，EDX，VSM，XRD和TEM分析对磁性纳米粒子进行了表征。使用\（\ hbox H} _ 2} \ hbox O} _ 2} \）作为氧化剂由苯基硼酸合成酚的过程进展顺利，收率很高。非均相催化剂，易于回收利用，温和的反应条件，较短的反应时间是本方案的优点。 图形概要设计了一种非常温和，快速且有效的方案，用于使用\（\ hbox CuFe} _ 2} \ hbox O} _ 4} \）磁性纳米颗粒（MNP）从苯基硼酸制备苯酚。催化剂。非均相催化剂，易于回收利用，是该方案的一项优势。