2-methyl-3-(thien-2-ylcarbonyl)benzofuran-5,6-dicarbonitrile | 1192655-99-4

• 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: 2-methyl-3-(thien-2-ylcarbonyl)benzofuran-5,6-dicarbonitrile
• 英文别名: 2-Methyl-3-[(thiophen-2-yl)carbonyl]-1-benzofuran-5,6-dicarbonitrile；2-methyl-3-(thiophene-2-carbonyl)-1-benzofuran-5,6-dicarbonitrile
• CAS: 1192655-99-4
• 化学式: C₁₆H₈N₂O₂S
• 分子量: 292.318
• InChiKey: NVFNWRIDIGJQNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 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：
  106
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-methyl-3-(thien-2-ylcarbonyl)benzofuran-5,6-dicarbonitrile 在 polyphosphoric acid 作用下， 反应 3.0h， 以43%的产率得到2-methyl-3-(thiophene-2-carbonyl)-5H-furo[2,3-f]isoindole-5,7(6H)-dione
  参考文献：
  名称：

  Synthesis of Functional Derivatives of Benzofuran-5,6-dicarboxylic Acids

  摘要：

  Synthetic routes to novel substituted benzofuran-5,6-dicarboxylic acids and furo[2,3-f]isoindole-5,7-diones via acid hydrolysis of the corresponding benzofuran-5,6-dicarbonitriles were developed.

  DOI：

  10.1134/s1070363219060276
• 作为产物：
  描述：

  、 4-溴-5-硝基-1,2-苯二甲腈 在 盐酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以53%的产率得到2-methyl-3-(thien-2-ylcarbonyl)benzofuran-5,6-dicarbonitrile
  参考文献：
  名称：

  Synthesis of 5,6-dicyanobenzofurans based on 4-bromo-5-nitrophthalonitrile

  摘要：

  A new stereoselective method for the synthesis of substituted 5,6-dicyanobenzofurans by activated aromatic nucleophilic replacement of a bromine atom and a nitro group in 4-bromo-5-nitrophthalonitrile has been developed.

  DOI：

  10.1016/j.mencom.2009.11.013

文献信息

• Reduction of 3-carbonyl-substituted 5,6-dicyanobenzofurans with sodium borohydride
  作者：Zh. V. Chirkova、S. I. Filimonov、I. G. Abramov、S. I. Firgang、G. A. Stashina

  DOI：10.1007/s11172-011-0256-y

  日期：2011.8

  AbstactReduction of 3-R-carbonyl-substituted 5,6-dicyanobenzofurans with sodium borohydride was studied under various conditions. 3-R-Carbonyl-substituted 5,6-dicyanobenzofurans are selectively reduced in ethanol to substituted 3-R-(hydroxymethyl)-5,6-dicyano-2-methylbenzofurans, products of more deep reduction, viz., substituted 3-R-(hydroxymethyl)-2-methyl-2,3-dihydro-5,6-dicyanobenzofurans, 3-R-(hydroxymethyl)-5

  摘要在各种条件下研究了 3-R-羰基取代的 5,6-二氰基苯并呋喃与硼氢化钠的还原反应。3-R-羰基取代的 5,6-二氰基苯并呋喃在乙醇中被选择性还原为取代的 3-R-（羟甲基）-5,6-二氰基-2-甲基苯并呋喃，这是更深度还原的产物，即取代的 3-R -(羟甲基)-2-甲基-2,3-二氢-5,6-二氰基苯并呋喃、3-R-(羟甲基)-5,6-二氰基-2-甲基苯并呋喃和 3-烷基取代的 4-羟基邻苯二甲腈是在四氢呋喃中形​​成。
• Formation of 4-hydroxy-5-[aryl(alkyl)-1H-pyrazol-4-yl]benzene-1,2-dicarbonitriles in reactions of benzofurans with hydrazines
  作者：Zh. V. Chirkova、M. V. Kabanova、D. V. Luferenko、S. I. Filimonov、I. G. Abramov

  DOI：10.1134/s1070428015050103

  日期：2015.5

  Some regularities are discussed of the reaction between 3-substituted benzofuran-5,6-dicarbonitriles with hydrazines leading to the formation of new 4-hydroxy-5-[aryl(alkyl)-1H-pyrazol-4-yl]-benzene-1,2-dicarbonitriles.
• Transformation of 3-Aroylbenzofurans into 2-Arylbenzofurans
  作者：Zh. V. Chirkova、S. I. Filimonov、R. S. Begunov

  DOI：10.1134/s1070428023020148

  日期：2023.2
• Synthesis of 5,6-dicyanobenzofurans based on 4-bromo-5-nitrophthalonitrile
  作者：Sergei I. Filimonov、Zhanna V. Chirkova、Igor G. Abramov、Alexander S. Shashkov、Sergey I. Firgang、Galina A. Stashina

  DOI：10.1016/j.mencom.2009.11.013

  日期：2009.11

  A new stereoselective method for the synthesis of substituted 5,6-dicyanobenzofurans by activated aromatic nucleophilic replacement of a bromine atom and a nitro group in 4-bromo-5-nitrophthalonitrile has been developed.
• Synthesis of Functional Derivatives of Benzofuran-5,6-dicarboxylic Acids
  作者：Zh. V. Chirkova、S. I. Filimonov、I. G. Abramov

  DOI：10.1134/s1070363219060276

  日期：2019.6

  Synthetic routes to novel substituted benzofuran-5,6-dicarboxylic acids and furo[2,3-f]isoindole-5,7-diones via acid hydrolysis of the corresponding benzofuran-5,6-dicarbonitriles were developed.