1-(4-methoxyphenyl)-2-methylnaphtho[2,1-b]furan | 1268831-57-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 1-(4-methoxyphenyl)-2-methylnaphtho[2,1-b]furan
• 英文别名: 1-(4-Methoxyphenyl)-2-methylbenzo[e][1]benzofuran
• CAS: 1268831-57-7
• 化学式: C₂₀H₁₆O₂
• 分子量: 288.346
• InChiKey: SHXXMFDHOLAQET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  22.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-{[3-(4-methoxyphenyl)prop-2-yn-1-yl]oxy}naphthalene 在 cesium fluoride 、 N,N-二乙基苯胺 作用下， 反应 0.42h， 以89%的产率得到1-(4-methoxyphenyl)-2-methylnaphtho[2,1-b]furan
  参考文献：
  名称：

  Microwave-assisted Claisen rearrangement of naphthyl 2-propynyl ethers: synthesis of naphthofurans

  摘要：

  An efficient two-step approach for the synthesis of naphtho[1,2-b]furans and naphtho[2,1-b]furans has been developed. Various functionalized propargyl alcohols were etherified with alpha- or beta-naphthol under Mitsunobu reaction conditions to give naphthyl 2-propynyl ethers, which underwent a facile microwave-assisted Claisen rearrangement and concomitant anionic cyclization to yield naphthofuran derivatives under basic reaction conditions. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.08.053

文献信息

• Indium Triflate-Catalyzed Coupling between Nitroalkenes and Phenol/Naphthols: A Simple and Direct Synthesis of Arenofurans by a Cyclization Reaction
  作者：Dhiman Kundu、Md Samim、Adinath Majee、Alakananda Hajra

  DOI：10.1002/asia.201000869

  日期：2011.2.1

  eye: A simple and efficient protocol for the synthesis of benzofuran and naphthofuran derivatives catalyzed by indium triflate was developed by coupling α,β‐unsaturated nitroalkenes with phenol/naphthols. The present method provides arenofuran derivatives in one pot from readily available starting materials (DCE=1,2‐dichloroethane; see scheme).

  呋喃眼（ Fan Eye）：通过将α，β-不饱和硝基烯烃与苯酚/萘酚偶联，开发了一种简单有效的由三氟甲磺酸铟催化的苯并呋喃和萘呋喃衍生物的合成方案。本方法可从一应俱全的起始原料（DCE = 1,2-二氯乙烷;参见方案）中在一锅中提供苯并呋喃衍生物。
• Facile synthesis of benzoindoles and naphthofurans through carbonaceous material-catalyzed cyclization of naphthylamines/naphthols with nitroolefins in water
  作者：Furen Zhang、Chunmei Li、Chen Wang、Chenze Qi

  DOI：10.1039/c5ob00129c

  日期：——

  A facile and efficient approach has been established for the synthesis of benzoindole and naphthofuran derivatives via the metal-free cyclization reaction of nitroolefins with naphthylamines/naphthols. Various substituted benzoindoles and naphthofurans are obtained in good to excellent yields. Moreover, the ability to recycle the carbonaceous material makes this method quite cost-effective and environmentally

  已经建立了通过硝基烯烃与萘胺/萘酚的无金属环化反应合成苯并吲哚和萘呋喃衍生物的简便有效方法。得到各种取代的苯并吲哚和萘呋喃，收率良好至优异。此外，与传统的酸催化方法相比，碳质材料的再循环能力使该方法具有很高的成本效益和环境友好性。理论研究表明，由该固体酸催化的萘胺与硝基烯烃之间的反应在热力学上控制在60°C，导致苯并吲哚的形成。