2-(p-tolyl)benzofuran-3-carbonitrile

• 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-(p-tolyl)benzofuran-3-carbonitrile
• 英文别名: 2-(4-Methylphenyl)-1-benzofuran-3-carbonitrile；2-(4-methylphenyl)-1-benzofuran-3-carbonitrile
• 化学式: C₁₆H₁₁NO
• 分子量: 233.269
• InChiKey: PRWIIUMXLSHSHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  4-甲苯基乙炔 在 potassium phosphate 、 silver trifluoromethanesulfonate 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 21.0h， 生成 2-(p-tolyl)benzofuran-3-carbonitrile
  参考文献：
  名称：

  Silver-Mediated Direct C–H Cyanation of Terminal Alkynes with N-Isocyanoiminotriphenylphosphorane

  摘要：

  A direct cyanation of terminal alkynes for the synthesis of propionitrile derivatives, with the aid of silver salt using water additive, has been achieved. The cyano source used is N-isocyanoiminotriphenylphosphorane, which is nontoxic, safe, and easy to handle. This protocol is characterized by its operational simplicity, high efficiency with excellent yields, broad substrate scope, and greater functional group tolerance.

  DOI：

  10.1021/acs.orglett.7b02743

文献信息

• Cu(II)‐Mediated C−C/C−O Bond Formation via C−H/C−C Bond Cleavage: Access to Benzofurans Using Amide as a Traceless Directing Group
  作者：Shuling Yu、Ningning Lv、Zhanxiang Liu、Yuhong Zhang

  DOI：10.1002/adsc.201901316

  日期：2020.1.7

  A copper‐mediated synthesis of 2,3‐disubstituted benzofurans with the assistance of an 8‐aminoquinolyl auxiliary is described from readily available benzamides and benzoylacetonitriles. In this reaction, the C−C bond is successfully constructed via C−H activation, and C−O bond is subsequently formed at the original position of the amide group in a one‐pot manner. The amide directing group is detached

  描述了一种由铜酰胺和苯甲酰基乙腈在8-氨基喹啉基助剂的辅助下通过铜介导的2,3-二取代苯并呋喃的合成方法。在该反应中，通过C-H活化成功地建立了C-C键，随后以单锅方式在酰胺基团的原始位置形成了C-O键。在反应条件下，通过C-C键断裂，酰胺导向基团同时脱离。令人惊讶地，可以通过使用氨作为胺源来改变反应条件来获得独特的异喹啉酮产物。
• Copper-Catalyzed Cascade Synthesis of 2-Aryl-3-cyanobenzofuran and Dibenzo[<i>b</i>,<i>f</i>]oxepine-10-carbonitrile Derivatives
  作者：Bharath Kumar Villuri、Sachin S. Ichake、Sabbasani Rajasekhara Reddy、Veerababurao Kavala、Vijayalakshmi Bandi、Chun-Wei Kuo、Ching-Fa Yao

  DOI：10.1021/acs.joc.8b01443

  日期：2018.9.7

  The copper-catalyzed reaction of aryl aldehydes with 2-iodobenzylcyanides afforded 2-aryl-3-cyanobenzofurans in isolated yields of up to 74% in a cascade manner, which involves Knoevenagel condensation, aryl hydroxylation, oxa-Michael addition, and aromatization reactions. Conversely, 2-halo benzaldehydes as reacting partners with 2-iodobenzylcyanide regioselectively furnished dibenzo[b,f]oxepine-10-carbonitrile

  芳基醛与2-碘苄基氰化物的铜催化反应以级联方式分离的产率高达74％，提供了2-芳基-3-氰基苯并呋喃，这涉及Knoevenagel缩合，芳基羟基化，氧杂-Michael加成和芳构化反应。相反，通过串联Knoevenagel缩合，芳基羟基化和Ullmann偶联反应，2-卤代苯甲醛作为与2-碘苄基氰化物区域选择性提供的二苯并[ b，f ]氧杂环丁-10腈衍生物的反应伙伴，分离产率高达85％。
• Silver-Mediated Direct C–H Cyanation of Terminal Alkynes with <i>N</i>-Isocyanoiminotriphenylphosphorane
  作者：Hannan Wang、Pengbing Mi、Wanjun Zhao、Ravi Kumar、Xihe Bi

  DOI：10.1021/acs.orglett.7b02743

  日期：2017.10.20

  A direct cyanation of terminal alkynes for the synthesis of propionitrile derivatives, with the aid of silver salt using water additive, has been achieved. The cyano source used is N-isocyanoiminotriphenylphosphorane, which is nontoxic, safe, and easy to handle. This protocol is characterized by its operational simplicity, high efficiency with excellent yields, broad substrate scope, and greater functional group tolerance.