4-(4-cyanophenyl)-6-diazo-2-(4-methoxyphenyl)-4H-thieno[3,2-b]pyridine-5,7-dione | 743354-07-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡啶类
• 英文名称: 4-(4-cyanophenyl)-6-diazo-2-(4-methoxyphenyl)-4H-thieno[3,2-b]pyridine-5,7-dione
• 英文别名: 4-(4-Cyanophenyl)-6-diazonio-2-(4-methoxyphenyl)-7-oxothieno[3,2-b]pyridin-5-olate
• CAS: 743354-07-6
• 化学式: C₂₁H₁₂N₄O₃S
• 分子量: 400.417
• InChiKey: HVRITTJMCXOCGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  133
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-(4-cyanophenyl)-6-diazo-2-(4-methoxyphenyl)-4H-thieno[3,2-b]pyridine-5,7-dione 在 dirhodium(II) tetrakis(perfluorobutyrate) 作用下， 以 苯 为溶剂， 反应 10.0h， 以71%的产率得到4-(4-cyanophenyl)-2-(4-methoxyphenyl)-5,6-dihydro-4H-thieno[3,2-b]pyrrol-5-one
  参考文献：
  名称：

  Facile Synthesis of 4-Alkyl (and Aryl)-2-aryl-6-diazo-4H- thieno[3,2-b]pyridine-5,7-diones

  摘要：

  Treatment of 3-{3-alkyl (and aryl)amino-5-arylthieno-2-yl}-2-diazo-3-oxopropanoates 8 with TMSOTf (3 equiv) in the presence of Et3N (6 equiv) in CH2Cl2 for 1 h at room temperature afforded 4-alkyl (and aryl)-2-aryl-6-diazo-4H-thieno[3,2-b]pyridine-5,7-diones 14 in excellent yields. On heating of 14 in the presence of a catalytic amount of Rh-2(CF3CF2CF2CO2)(4) in PhH for 4-10 h at reflux, corresponding ring contraction products, 4-alkyl (and aryl)-5,6-dihydro-4H-thieno[3,2-b]pyrrol-5-ones 16, were produced in good to excellent yields.

  DOI：

  10.1021/jo049769a
• 作为产物：
  描述：

  1-(4-甲氧基苯基)-3,3-二(甲硫基)-2-丙烯-1-酮 在 劳森试剂 、 4-二甲氨基吡啶 、 三氟化硼乙醚 、 mercury(II) diacetate 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 、 苯 为溶剂， 反应 3.0h， 生成 4-(4-cyanophenyl)-6-diazo-2-(4-methoxyphenyl)-4H-thieno[3,2-b]pyridine-5,7-dione
  参考文献：
  名称：

  Facile Synthesis of 4-Alkyl (and Aryl)-2-aryl-6-diazo-4H- thieno[3,2-b]pyridine-5,7-diones

  摘要：

  Treatment of 3-{3-alkyl (and aryl)amino-5-arylthieno-2-yl}-2-diazo-3-oxopropanoates 8 with TMSOTf (3 equiv) in the presence of Et3N (6 equiv) in CH2Cl2 for 1 h at room temperature afforded 4-alkyl (and aryl)-2-aryl-6-diazo-4H-thieno[3,2-b]pyridine-5,7-diones 14 in excellent yields. On heating of 14 in the presence of a catalytic amount of Rh-2(CF3CF2CF2CO2)(4) in PhH for 4-10 h at reflux, corresponding ring contraction products, 4-alkyl (and aryl)-5,6-dihydro-4H-thieno[3,2-b]pyrrol-5-ones 16, were produced in good to excellent yields.

  DOI：

  10.1021/jo049769a

文献信息

• Facile Synthesis of 4-Alkyl (and Aryl)-2-aryl-6-diazo-4<i>H</i>- thieno[3,2-<i>b</i>]pyridine-5,7-diones
  作者：Dong Joon Lee、Kyongtae Kim

  DOI：10.1021/jo049769a

  日期：2004.7.1

  Treatment of 3-3-alkyl (and aryl)amino-5-arylthieno-2-yl}-2-diazo-3-oxopropanoates 8 with TMSOTf (3 equiv) in the presence of Et3N (6 equiv) in CH2Cl2 for 1 h at room temperature afforded 4-alkyl (and aryl)-2-aryl-6-diazo-4H-thieno[3,2-b]pyridine-5,7-diones 14 in excellent yields. On heating of 14 in the presence of a catalytic amount of Rh-2(CF3CF2CF2CO2)(4) in PhH for 4-10 h at reflux, corresponding ring contraction products, 4-alkyl (and aryl)-5,6-dihydro-4H-thieno[3,2-b]pyrrol-5-ones 16, were produced in good to excellent yields.