3-(2-phenylbenzofuran-3-yl)propanenitrile | 1131341-92-8

• 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: 3-(2-phenylbenzofuran-3-yl)propanenitrile
• 英文别名: 3-(2-phenylbenzofuran-3-yl)propionitrile；3-(2-Phenyl-1-benzofuran-3-yl)propanenitrile；3-(2-phenyl-1-benzofuran-3-yl)propanenitrile
• CAS: 1131341-92-8
• 化学式: C₁₇H₁₃NO
• 分子量: 247.296
• InChiKey: JLSGOLKKEFKHOS-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：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 camphor-10-sulfonic acid 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以32 mg的产率得到3-(2-phenylbenzofuran-3-yl)propanenitrile
  参考文献：
  名称：

  Interrupting Base-Mediated Benzofuran Ring Transformation with Michael Acceptors

  摘要：

  A simple two-stage approach for the synthesis of 3-(2-arylbenzofuran-3-yl)propanoates and propanamides has been developed employing simple acrylates and acrylamides and readily available 3-aroylbenzofurans. The key step of this process involves a base-mediated ring opening of the 3-aroylbenzofurans and subsequent Michael addition of the resulting 1,3-dicarbonyl intermediate with acrylate/acrylamide, followed by the deformylation in one-pot. The resulting products undergo an acid-mediated dehydrative cyclization to arrive at these targets.

  DOI：

  10.1021/acs.joc.7b01267

文献信息

• Domino rhodium(I)-catalysed reactions for the efficient synthesis of substituted benzofurans and indoles
  作者：Alistair Boyer、Naohiro Isono、Sebastian Lackner、Mark Lautens

  DOI：10.1016/j.tet.2010.05.106

  日期：2010.8

  Rhodium(I) catalysts promote the transformation of o-alkynyl phenols and anilines to the corresponding benzo[b]furans and indoles. The reaction is postulated to proceed via a transient 3-rhodium heterocycle intermediate, which can be trapped with suitable electrophiles to give poly-substituted heterocycles. In the case of mono-substituted electron-withdrawn electrophiles, excellent yield and selectivity

  铑（I）催化剂促进邻炔基苯酚和苯胺转化为相应的苯并[ b ]呋喃和吲哚。假定该反应通过过渡的3-铑杂环中间体进行，该中间体可以用合适的亲电试剂捕获以得到多取代的杂环。在单取代的吸电子亲电体的情况下，与Heck-Mizoroki反应相比，可以获得优异的收率和选择性。在2-炔基吡啶亲电试剂的情况下，形成新的2-（苯并呋喃-3-基）乙烯基吡啶。
• Rhodium(I)-Catalyzed Cyclization Reaction of <i>o</i>-Alkynyl Phenols and Anilines. Domino Approach to 2,3-Disubstituted Benzofurans and Indoles
  作者：Naohiro Isono、Mark Lautens

  DOI：10.1021/ol9001174

  日期：2009.3.19

  A rhodium-catalyzed cyclization of o-alkynylphenols and anilines followed by intermolecular conjugate addition that succeeds with alkyl and aryl alkynes is reported. In this reaction, 2,3-disubstituted benzofurans or indoles are obtained in one pot in good to excellent yields.