2-(4-methoxyphenyl)benzofuran-3-carbonitrile | 1225336-00-4

• 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-methoxyphenyl)benzofuran-3-carbonitrile
• 英文别名: 2-(4-Methoxyphenyl)-1-benzofuran-3-carbonitrile
• CAS: 1225336-00-4
• 化学式: C₁₆H₁₁NO₂
• 分子量: 249.269
• InChiKey: ISAOQOQULUMOKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  水杨醛 、 对甲氧基苯乙腈 在 sodium methylate 、 copper diacetate 作用下， 以 二甲基亚砜 为溶剂， 反应 15.0h， 以47%的产率得到2-(4-methoxyphenyl)benzofuran-3-carbonitrile
  参考文献：
  名称：

  Copper-Catalyzed Preparation of 2-Aryl-3-cyanobenzofurans with Bright Blue Photoluminescence

  摘要：

  Copper-catalyzed cascade synthesis of 2-aryl-3-cyanobefizaurans from o-hydroxybenzaldehydes and arylacetonitriles in the presence of copper acetate and sodium methoxide is reported. The synthesized 2-aryl-3-cyanobenzofurans emit bright blue under IN light with a quantum yield up to 88.9%.

  DOI：

  10.1021/acs.orglett.5b03704

文献信息

• Copper-Mediated Cyclization−Halogenation and Cyclization−Cyanation Reactions of β-Hydroxyalkynes and <i>o</i>-Alkynylphenols and Anilines
  作者：Nalivela Kumara Swamy、Arife Yazici、Stephen G. Pyne

  DOI：10.1021/jo1005119

  日期：2010.5.21

  The CuX (X = I, Br, Cl, CN)-mediated cyclization−halogenation and cyclization−cyanation reactions of β-hydroxyalkynes and o-alkynylphenol and -aniline derivatives give rise to 3-halo- and 3-cyanofuro[3,2-b]pyrroles, 3-iodo-, 3-bromo-, and 3-cyanobenzofurans, and 3-cyanoindoles, respectively.

  CuX（X = I，Br，Cl，CN）介导的β-羟基炔烃与邻炔基苯酚和-苯胺衍生物的环化-卤化和环化-氰化反应生成3-卤代和3-氰基呋喃[3,2 - b ]吡咯，3-碘，3-溴-和3- cyanobenzofurans和3- cyanoindoles，分别。
• 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％。
• Copper-Catalyzed Preparation of 2-Aryl-3-cyanobenzofurans with Bright Blue Photoluminescence
  作者：Lianpeng Zhang、Zhixing Peng、Qiaodong Wen、Xihui Li、Ping Lu、Yanguang Wang

  DOI：10.1021/acs.orglett.5b03704

  日期：2016.2.19

  Copper-catalyzed cascade synthesis of 2-aryl-3-cyanobefizaurans from o-hydroxybenzaldehydes and arylacetonitriles in the presence of copper acetate and sodium methoxide is reported. The synthesized 2-aryl-3-cyanobenzofurans emit bright blue under IN light with a quantum yield up to 88.9%.