7-氟-1,2,3,4-四氢二苯并呋喃 | 823787-32-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 7-氟-1,2,3,4-四氢二苯并呋喃
• 英文名称: 7-fluoro-1,2,3,4-tetrahydrodibenzo[b,d]furan
• 英文别名: 8-fluoro-1,2,3,4-tetrahydrodibenzofuran；7-fluoro-1,2,3,4-tetrahydrodibenzofuran
• CAS: 823787-32-2
• 化学式: C₁₂H₁₁FO
• 分子量: 190.217
• InChiKey: FZPGOXMOCXXPLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  2-(2-bromo-4-fluorophenyl)cyclohexen-1-yl triflate 在 copper(l) iodide 氢氧化钾 、 四甲基乙二胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 16.0h， 以96%的产率得到7-氟-1,2,3,4-四氢二苯并呋喃
  参考文献：
  名称：

  Copper-catalysed benzofuran synthesis: developing aryl bromide–alkenyl triflates as general heterocycle precursors

  摘要：

  A range of conjugated aryl bromide-alkenyl triflates, previously described as indole precursors, are efficiently converted to the corresponding benzofurans when treated with CuI/TMEDA and potassium hydroxide. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.08.109

文献信息

• Dehydrative C–H Alkylation and Alkenylation of Phenols with Alcohols: Expedient Synthesis for Substituted Phenols and Benzofurans
  作者：Dong-Hwan Lee、Ki-Hyeok Kwon、Chae S. Yi

  DOI：10.1021/ja302710v

  日期：2012.5.2

  well-defined cationic Ru-H complex catalyzes the dehydrative C-H alkylation reaction of phenols with alcohols to form ortho-substituted phenol products. Benzofuran derivatives are efficiently synthesized from the dehydrative C-H alkenylation and annulation reaction of phenols with 1,2-diols. The catalytic C-H coupling method employs cheaply available phenols and alcohols, exhibits a broad substrate scope, tolerates

  明确定义的阳离子 Ru-H 络合物催化苯酚与醇的脱水 CH 烷基化反应，形成邻位取代的苯酚产物。苯并呋喃衍生物是由苯酚与 1,2-二醇的脱水 CH 烯基化和环化反应有效合成的。催化 CH 偶联方法使用廉价的酚类和醇类，表现出广泛的底物范围，耐受羰基和胺官能团，并释放水作为唯一的副产物。
• Cascade Palladium-Catalyzed Direct Intramolecular Arylation/Alkene Isomerization Sequences: Synthesis of Indoles and Benzofurans
  作者：Myriam Yagoubi、Ana C. F. Cruz、Paula L. Nichols、Richard L. Elliott、Michael C. Willis

  DOI：10.1002/anie.201004097

  日期：2010.10.18

  One route, two cycles: A palladium‐catalyzed intramolecular direct arylation reaction combined with an isomerization step provided a straightforward synthetic route to both indoles and benzofurans (see scheme). Isolation and functionalization of intermediate alkene isomers allowed the formation of variants having substituents remote from the core.

  一种途径，两个循环：钯催化的分子内直接芳基化反应与异构化步骤相结合，提供了直接合成吲哚和苯并呋喃的途径（参见方案）。中间烯烃异构体的分离和官能化允许形成具有远离核的取代基的变体。
• Palladium-catalysed intramolecular enolate O-arylation and thio-enolate S-arylation: synthesis of benzo[b]furans and benzo[b]thiophenes
  作者：Michael C. Willis、Dawn Taylor、Adam T. Gillmore

  DOI：10.1016/j.tet.2006.05.004

  日期：2006.12

  Enolates derived from alpha-(ortho-haloaryl)-substituted ketones undergo palladium-catalysed C-O bond formation to deliver benzofuran products in good yield. A catalyst generated from Pd-2(dba)(3) and the ligand DPEphos effects the key bond formation to deliver a variety of substituted products from both cyclic and acyclic precursors. The analogous thio-ketones undergo C-S bond formation using identical reaction conditions and are converted to benzothiophene products. A cascade sequence that produces the required a-aryl ketones in situ has also been developed, although the substrate scope is more restricted. (c) 2006 Elsevier Ltd. All rights reserved.
• Palladium-Catalyzed Intramolecular <i>O</i>-Arylation of Enolates:  Application to Benzo[<i>b</i>]furan Synthesis
  作者：Michael C. Willis、Dawn Taylor、Adam T. Gillmore

  DOI：10.1021/ol047993g

  日期：2004.12.1

  A catalyst generated from Pd-2(dba)(3) and the ligand DPEphos effects intramolecular C-O bond formation between enolates and aryl halides in the conversion of 1-(2-haloaryl)ketones directly into the corresponding benzofurans. Both cyclic and acyclic ketones are efficient substrates. Thio ketones can also be employed allowing the preparation of the corresponding benzothiophenes.
• Copper-catalysed benzofuran synthesis: developing aryl bromide–alkenyl triflates as general heterocycle precursors
  作者：Andrew C. Tadd、Mark R. Fielding、Michael C. Willis

  DOI：10.1016/j.tetlet.2007.08.109

  日期：2007.10

  A range of conjugated aryl bromide-alkenyl triflates, previously described as indole precursors, are efficiently converted to the corresponding benzofurans when treated with CuI/TMEDA and potassium hydroxide. (C) 2007 Elsevier Ltd. All rights reserved.