2-(4-fluorophenyl)-5-nitro-1-benzofuran | 101993-20-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 2-(4-fluorophenyl)-5-nitro-1-benzofuran
• 英文别名: Benzofuran,2-(4-fluorophenyl)-5-nitro-
• CAS: 101993-20-8
• 化学式: C₁₄H₈FNO₃
• 分子量: 257.221
• InChiKey: NUQIHXMPROSGRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-[2-(4-Fluorophenyl)ethynyl]-4-nitrophenol 在 1-butyl-3-methylimidazolium hydroxide 作用下， 反应 2.5h， 以97%的产率得到2-(4-fluorophenyl)-5-nitro-1-benzofuran
  参考文献：
  名称：

  Recyclable [bmIm]OH promoted one-pot heterocyclization: synthesis of substituted benzofurans

  摘要：

  A single step access to polysubstituted benzo[b]furans has been achieved under simple and eco-compatible conditions. The heterocyclization proceeded efficiently. [bmIm]OH played a triple role as a solvent, base as well as catalyst. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.150

文献信息

• Mechanistic Insights on Orthogonal Selectivity in Heterocycle Synthesis
  作者：Arun Maji、Yernaidu Reddi、Raghavan B. Sunoj、Debabrata Maiti

  DOI：10.1021/acscatal.8b02537

  日期：2018.11.2

  Recently, we have developed a method for catalytic regioselective synthesis of 2-substituted and 3-substituted benzofurans starting from phenols. The choice of reacting partner, olefin versus α,β-unsaturated acid, is critical to dictate the isomeric product formation. Instances are known where these olefinic partners did not complement each other and yield a similar outcome. In the current work, we

  最近，我们已经开发了一种从苯酚开始催化区域选择性合成2取代和3取代的苯并呋喃的方法。选择反应伙伴，烯烃还是α，β-不饱和酸，对决定异构产物的形成是至关重要的。已知这些烯烃伙伴彼此不互补且产生相似结果的情况。在当前的工作中，我们解决了这一悖论，重点是（a）正交选择性的起源和（b）预期互补行为的关键要求。实验和计算研究提供了重要的力学见解。发现在迁移插入过程中的静电相容性和在催化步骤中羧酸部分的定位在确定区域选择性方面发挥了至关重要的作用。
• Sequential and One-Pot Reactions of Phenols with Bromoalkynes for the Synthesis of (<i>Z</i>)-2-Bromovinyl Phenyl Ethers and Benzo[<i>b</i>]furans
  作者：Shihua Wang、Pinhua Li、Lin Yu、Lei Wang

  DOI：10.1021/ol202383z

  日期：2011.11.18

  2-substituted benzo[b]furans in good yields through palladium-catalyzed direct C–H bond functionalizations. It is important to note that the transformation of phenols with bromoalkynes into benzo[b]furans could be carried out in one pot with a simple and efficient tandem procedure.

  苯并[ b ]呋喃在一个锅中根据苯酚与溴炔烃的加成/钯催化的CH键结合官能化制备。苯酚与溴代炔烃的加成反应以高收率生成了具有优异区域和立体选择性的（Z）-2-溴乙烯基苯基醚。所获得的（Z）-2-溴乙烯基苯基醚随后通过分子内环化进行处理，通过钯催化的直接C–H键官能化，以高收率获得了2-取代的苯并[ b ]呋喃。重要的是要注意，可以将溴代炔烃将苯酚转化为苯并[ b ]呋喃，可以通过简单而有效的串联程序在一个罐中进行。
• MAJDIK, CORNELIA;KOVENDI, ALEXANDRU;MATEI, SIMION;BREAZU, DORIN, REV. CHIM., 40,(1989) N, C. 689-693
  作者：MAJDIK, CORNELIA、KOVENDI, ALEXANDRU、MATEI, SIMION、BREAZU, DORIN

  DOI：——

  日期：——
• Recyclable [bmIm]OH promoted one-pot heterocyclization: synthesis of substituted benzofurans
  作者：I.R. Siddiqui、Malik Abdul Waseem、Shayna Shamim、Shireen、Arjita Srivastava、Anjali Srivastava

  DOI：10.1016/j.tetlet.2013.05.150

  日期：2013.8

  A single step access to polysubstituted benzo[b]furans has been achieved under simple and eco-compatible conditions. The heterocyclization proceeded efficiently. [bmIm]OH played a triple role as a solvent, base as well as catalyst. (C) 2013 Elsevier Ltd. All rights reserved.