6,7-dimethyl-1,3-dihydrothieno<3,4-b>quinoxaline 2-oxide | 173344-33-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 6,7-dimethyl-1,3-dihydrothieno<3,4-b>quinoxaline 2-oxide
• 英文别名: 6,7-Dimethyl-1,3-dihydrothieno[3,4-b]quinoxaline 2-oxide
• CAS: 173344-33-7
• 化学式: C₁₂H₁₂N₂OS
• 分子量: 232.306
• InChiKey: USFKFMBGLKXDJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  62.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6,7-dimethyl-1,3-dihydrothieno<3,4-b>quinoxaline 2-oxide 在 氢氧化钾 作用下， 以 苯 为溶剂， 反应 5.0h， 以40%的产率得到6,7-dimethylthieno<3,4-b>quinoxaline
  参考文献：
  名称：

  Synthesis of Thieno[3,4-b]quinoxaline and Derivatives

  摘要：

  The highly reactive o-quinonoid heterocycles thieno[3,4-b]quinoxaline (1a) and its 6,7-dimethyl derivative (1b) have been synthesized by a base-catalyzed Pummerer reaction and isolated in crystalline form. In contrast, the 1,3-dibromothieno[3,4-b]quinoxaline (8) could be characterized in solution but not isolated in pure farm. The readily prepared 1,3-dihydrothieno[3,4-b]quinoxaline (5a) underwent a direct Knoevenagel condensation with thiophene-2-carboxaldehyde to give the stilbenoid 14a. Sulfide 5a was also converted in a two-step process to the stable 1,3-diformylthieno[3,4-b]quinoxaline 11a.

  DOI：

  10.1021/jo00130a032
• 作为产物：
  描述：

  2,3-bis(bromomethyl)-6,7-dimethylquinoxaline 在 sodium sulfide 、 magnesium monoperoxyphthalate 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 0.67h， 生成 6,7-dimethyl-1,3-dihydrothieno<3,4-b>quinoxaline 2-oxide
  参考文献：
  名称：

  Synthesis of Thieno[3,4-b]quinoxaline and Derivatives

  摘要：

  The highly reactive o-quinonoid heterocycles thieno[3,4-b]quinoxaline (1a) and its 6,7-dimethyl derivative (1b) have been synthesized by a base-catalyzed Pummerer reaction and isolated in crystalline form. In contrast, the 1,3-dibromothieno[3,4-b]quinoxaline (8) could be characterized in solution but not isolated in pure farm. The readily prepared 1,3-dihydrothieno[3,4-b]quinoxaline (5a) underwent a direct Knoevenagel condensation with thiophene-2-carboxaldehyde to give the stilbenoid 14a. Sulfide 5a was also converted in a two-step process to the stable 1,3-diformylthieno[3,4-b]quinoxaline 11a.

  DOI：

  10.1021/jo00130a032

文献信息

• Synthesis of Thieno[3,4-b]quinoxaline and Derivatives
  作者：Joerg Pohmer、M. V. Lakshmikantham、Michael P. Cava

  DOI：10.1021/jo00130a032

  日期：1995.12

  The highly reactive o-quinonoid heterocycles thieno[3,4-b]quinoxaline (1a) and its 6,7-dimethyl derivative (1b) have been synthesized by a base-catalyzed Pummerer reaction and isolated in crystalline form. In contrast, the 1,3-dibromothieno[3,4-b]quinoxaline (8) could be characterized in solution but not isolated in pure farm. The readily prepared 1,3-dihydrothieno[3,4-b]quinoxaline (5a) underwent a direct Knoevenagel condensation with thiophene-2-carboxaldehyde to give the stilbenoid 14a. Sulfide 5a was also converted in a two-step process to the stable 1,3-diformylthieno[3,4-b]quinoxaline 11a.