2-苯基苯并[g][1]苯并呋喃 | 14385-53-6

• 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
• 中文名称: 2-苯基苯并[g][1]苯并呋喃
• 英文名称: 2-phenylnaphtho[1,2-b]furan
• 英文别名: 2-phenylbenzo[g][1]benzofuran
• CAS: 14385-53-6
• 化学式: C₁₈H₁₂O
• 分子量: 244.293
• InChiKey: QWCZUUROBYBSPP-UHFFFAOYSA-N

物化性质

• 熔点：
  88-90 °C(Solv: ethanol (64-17-5))
• 沸点：
  422.8±14.0 °C(Predicted)
• 密度：
  1.187±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-苯基苯并[g][1]苯并呋喃 以75%的产率得到
  参考文献：
  名称：

  BASTIAN, G.;ROYER, R., EUR. J. MED. CHEM., 1984, 19, N 2, 157-160

  摘要：

  DOI：
• 作为产物：
  描述：

  1-羟基-2-奈甲醛 在 sodium acetate 、 乙酸酐 、 potassium carbonate 、 potassium hydroxide 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 2-苯基苯并[g][1]苯并呋喃
  参考文献：
  名称：

  Synthesis and biological evaluation of 2-arylbenzofuran derivatives as potential anti-Alzheimer’s disease agents

  摘要：

  Alzheimer's disease (AD) is a type of progressive dementia caused by degeneration of the nervous system. A single target drug usually does not work well. Therefore, multi-target drugs are designed and developed so that one drug can specifically bind to multiple targets to ensure clinical effectiveness and reduce toxicity. We synthesised a series of 2-arylbenzofuran derivatives and evaluated their in vitro activities. 2-Arylbenzofuran compounds have good dual cholinesterase inhibitory activity and β-secretase inhibitory activity. The IC50 value of compound 20 against acetylcholinesterase inhibition (0.086 ± 0.01 µmol·L-1) is similar to donepezil (0.085 ± 0.01 µmol·L-1) and is better than baicalein (0.404 ± 0.04 µmol·L-1). And most of the compounds have good BACE1 inhibitory activity, of which 3 compounds (8, 19 and 20) show better activity than baicalein (0.087 ± 0.03 µmol·L-1). According to experimental results, 2-arylbenzofuran compounds provide an idea for drug design to develop prevention and treatment for AD.

  DOI：

  10.1080/14756366.2021.1940993

文献信息

• Strategy for Overcoming Full Reversibility of Intermolecular Radical Addition to Aldehydes: Tandem C–H and C–O Bonds Cleaving Cyclization of (Phenoxymethyl)arenes with Carbonyls to Benzofurans
  作者：Hong-Xing Zheng、Xiang-Huan Shan、Jian-Ping Qu、Yan-Biao Kang

  DOI：10.1021/acs.orglett.8b01207

  日期：2018.6.1

  An intermolecular addition of carbon radicals enabled by a cascade radical coupling strategy is developed. It includes an intermolecular alkyl radical addition to a carbonyl group followed by an intramolecular alkoxy radical addition to haloarenes and produces substituted benzofurans in high yields. The radical nature of this reaction is explored by radical trapping experiments and EPR analysis. The

  通过级联自由基偶联策略实现了碳自由基的分子间加成。它包括向羰基的分子间烷基加成，然后向卤代芳烃的分子内烷氧基加成，并以高收率产生取代的苯并呋喃。通过自由基捕获实验和EPR分析，探索了该反应的自由基性质。通过KIE实验和控制实验研究了该机理。该方法可以快速，实用地获得TAM-16的关键中间体，TAM-16是治疗结核病的安全有效的抗菌剂，因此，对有机合成和制药工业具有重要意义。
• Copper/P(<i>t</i> Bu)₃ -Mediated Regiospecific Synthesis of Fused Furans and Naphthofurans
  作者：Togati Naveen、Arghya Deb、Debabrata Maiti

  DOI：10.1002/anie.201609401

  日期：2017.1.19

  to construct substituted fused furans and naphthofurans from readily available starting materials under mild reaction conditions. The utility of the method is further demonstrated by the synthesis of chiral furans from (R)‐(−)‐carvone and (S)‐(+)‐carvone. A plausible mechanism involving the oxidative radical cyclization has been suggested based on experimental observations.

  一种新颖的[3 + 2]的各种环酮和多样的烯烃或炔烃的环加成之间可以通过铜组合有效地促进了与三叔丁基膦[P（吨丁基）3 ]配体。该方案显示出极好的选择性，并以良好或优异的产率提供了一组示例性的稠合杂环。当前的策略还代表了一种非常简单且经济的方法，可以在温和的反应条件下，从容易获得的原料中构建取代的呋喃呋喃和萘呋喃。由（R）-（-）-香芹酮和（S）-（+）-香芹酮。根据实验观察结果，提出了一种可能的机制，涉及氧化自由基环化。
• A concise route to functionalized benzofurans directly from gem-dibromoalkenes and phenols
  作者：Maddali L. N. Rao、Priyabrata Dasgupta

  DOI：10.1039/c5ra13213d

  日期：——

  A tandem strategy for the construction of benzofuran motifs has been developed directly from gem-dibromoalkenes and phenols under palladium-catalyzed conditions.

  已经开发了一种从gem-二溴代烯烃和酚直接在钯催化条件下构建苯并呋喃基团的串联策略。
• Acid-promoted furan annulation and aromatization: An access to benzo[ b ]furan derivatives
  作者：Jun Ao、Yidong Liu、Shiqi Jia、Lu Xue、Dongmei Li、Yu Tan、Wenling Qin、Hailong Yan

  DOI：10.1016/j.tet.2017.11.049

  日期：2018.1

  An unprecedented PTSA-promoted furan annulation and aromatization in one pot has been developed. This process offers a simple and efficient synthetic route for the construction of various highly substituted benzo[b]furan derivatives, which are widely used not only in drug active molecules but also organic semiconductor and organic light-emitting devices. The preliminary mechanism study indicated this

  在一个锅中开发了前所未有的PTSA促进的呋喃环化和芳构化。该方法为构建各种高度取代的苯并[ b ]呋喃衍生物提供了简单而有效的合成途径，这些苯并[ b ]呋喃衍生物不仅广泛用于药物活性分子中，而且还广泛用于有机半导体和有机发光器件中。初步的机理研究表明，该转化通过呋喃环化和芳构化依次进行。
• Hydrazone–Pd-catalyzed direct intermolecular reaction of <i>o</i>-alkynylphenols with allylic acetates
  作者：Kohei Watanabe、Takashi Mino、Eri Ishikawa、Chihiro Masuda、Yasushi Yoshida、Masami Sakamoto

  DOI：10.1039/c7ob02873c

  日期：——

  We found that the hydrazone–Pd-catalyzed direct intermolecular reaction of o-alkynylphenols with allylic acetates afforded the corresponding 2-substituted-3-allylbenzofuran derivatives. This reaction proceeded smoothly at room temperature using a hydrazone–Pd catalyst system.

  我们发现the-Pd催化邻炔基苯酚与烯丙基乙酸酯的直接分子间反应可得到相应的2-取代-3-烯丙基苯并呋喃衍生物。使用-钯催化剂体系，该反应在室温下可顺利进行。