1,3-Dibromothieno[3,4-b]quinoxaline | 173344-26-8

• 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: 1,3-Dibromothieno[3,4-b]quinoxaline
• CAS: 173344-26-8
• 化学式: C₁₀H₄Br₂N₂S
• 分子量: 344.029
• InChiKey: AHIOOQDVUOJKTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-甲基马来酰亚胺 、 1,3-Dibromothieno[3,4-b]quinoxaline 以 丙酮 、 苯 为溶剂， 反应 12.0h， 生成 (1R,12S,13R,17S)-1,12-dibromo-15-methyl-18-thia-3,10,15-triazapentacyclo[10.5.1.02,11.04,9.013,17]octadeca-2,4,6,8,10-pentaene-14,16-dione 、 (1R,12S,13S,17R)-1,12-dibromo-15-methyl-18-thia-3,10,15-triazapentacyclo[10.5.1.02,11.04,9.013,17]octadeca-2,4,6,8,10-pentaene-14,16-dione
  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-双(溴甲基)喹喔啉 在 sodium sulfide 、 溴 、 sodium iodide 作用下， 以 乙醇 、 水 、 丙酮 、 苯 为溶剂， 反应 0.84h， 生成 1,3-Dibromothieno[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

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.