(2-fluoromethyl)furan | 67363-96-6

• 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: (2-fluoromethyl)furan
• 英文别名: furfuryl fluoride；2-(Fluoromethyl)furan
• CAS: 67363-96-6
• 化学式: C₅H₅FO
• 分子量: 100.093
• InChiKey: PWDLMCXYIKGCFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  糠醇 在 sulfur tetrafluoride 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以20%的产率得到(2-fluoromethyl)furan
  参考文献：
  名称：

  SF 4与醇的反应：2-（氟甲基）呋喃和2-氟-1-苯基乙烷的制备

  摘要：

  描述了用四氟化硫氟化（2-呋喃基）甲醇和2-苯基乙醇。反应在玻璃管中在三乙胺或吡啶在二氯甲烷或环己烷溶液中的存在下于-50°C进行。通过1 H和19 F NMR和质谱鉴定了（2-氟甲基）呋喃和2-氟-1-苯基乙烷的产物。

  DOI：

  10.1016/s0022-1139(00)83029-8

文献信息

• Modular Synthesis of Fluoro‐Substituted Furan Compounds via Controllable Fluorination of Biomass‐Based 5‐HMF and Its Derivatives
  作者：Ze‐Kuan Zhang、Wen‐Yan Xu、Tian‐Jun Gong、Yao Fu

  DOI：10.1002/cssc.202301072

  日期：2024.1.8

  In this study, we present an example of adjustable fluorination of biomass-derived 5-HMF and its oxygen-containing derivatives, synthesize a series of mono-fluoromethyl, difluoromethyl, and acylfluoro-substituted furan compounds. These fluoro-substituted furan compounds can be further transformed to prepare drug analogs, thereby offering a novel approach for the high-value utilization of biomass molecules

  在这项研究中，我们提出了一个对生物质衍生的5-HMF及其含氧衍生物进行可调节氟化的例子，合成了一系列单氟甲基、二氟甲基和酰基氟取代的呋喃化合物。这些氟代呋喃化合物可以进一步转化制备药物类似物，从而为生物质分子的高价值利用提供新的途径。
• Practical and General Method for Direct Synthesis of Alkyl Fluorides from Alcohols under Mild Conditions
  作者：Babasaheb P. Bandgar、Vinod T. Kamble、Ankush V. Biradar

  DOI：10.1007/s00706-005-0296-9

  日期：2005.9

  A variety of alcohols were treated with Ph3P and KF in CCl4-DMF at room temperature to afford the corresponding fluorides in very good yields.
• Synthesis of α-trifluoromethylated amides by Eschenmoser–Claisen-type rearrangement of allylic alcohols
  作者：Justyna Walkowiak、Magdalena Tomas-Szwaczyk、Günter Haufe、Henryk Koroniak

  DOI：10.1016/j.jfluchem.2012.07.011

  日期：2012.11

  A new, mild method to prepare alpha-trifluoromethylated amides bearing an additional trans-configured double bond in gamma-position is described. Treatment at room temperature of fluorinated and non-fluorinated allylic alcohols 1 and 2 with the 1,1,3,3,3-pentafluoropropene-diethylamine adduct (PFPDEA) in the presence of triethylamine as base gave the products of [3,3]-sigmatropic Eschenmoser-Claisen-type rearrangements with good yields and excellent diastereoselectivity due to chair-like conformations of transition states. Starting with enantiomerically enriched allylic alcohols chirality transfer from carbon 3 of the allylic system to carbon 2 of the final alpha-trifluoromethyl carboxamides was observed. This methodology was applied to both simple and more complex, including terpenic, allylic alcohols and might be developed to an alternative strategy to the well-known electrophilic alpha-trifluoromethylation of carbonyl compounds. (C) 2012 Elsevier B.V. All rights reserved.
• JANZEN, ALEXANDER F.;MARAT, RONALD KIRK, J. FLUOR. CHEM., 38,(1988) N 2, 205-208
  作者：JANZEN, ALEXANDER F.、MARAT, RONALD KIRK

  DOI：——

  日期：——
• Reaction of SF4 with alcohols: preparation of 2-(fluoromethyl) furan and 2-fluoro-1-phenylethane
  作者：Alexander F. Janzen、Ronald Kirk Marat

  DOI：10.1016/s0022-1139(00)83029-8

  日期：1988.1

  The fluorination of (2-furyl)methanol and 2-phenylethanol with sulfur tetrafluoride is described. The reactions were carried out in glass tubes at −50°C in the presence of triethylamine or pyridine in dichloromethane or cyclohexane solution. The products, (2-fluoromethyl) furan and 2-fluoro-1-phenylethane, were identified by 1H and 19F NMR and mass spectrometry.

  描述了用四氟化硫氟化（2-呋喃基）甲醇和2-苯基乙醇。反应在玻璃管中在三乙胺或吡啶在二氯甲烷或环己烷溶液中的存在下于-50°C进行。通过1 H和19 F NMR和质谱鉴定了（2-氟甲基）呋喃和2-氟-1-苯基乙烷的产物。