2,3-bis(bromomethyl)-5,7-bis(2-thienyl)thieno[3,4-b]pyrazine | 1359021-12-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 2,3-bis(bromomethyl)-5,7-bis(2-thienyl)thieno[3,4-b]pyrazine
• 英文别名: 2,3-bis(bromomethyl)-5,7-dithiophen-2-ylthieno[3,4-b]pyrazine
• CAS: 1359021-12-7
• 化学式: C₁₆H₁₀Br₂N₂S₃
• 分子量: 486.275
• InChiKey: TVTRYVWKOYHIPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3-bis(bromomethyl)-5,7-bis(2-thienyl)thieno[3,4-b]pyrazine 、 二乙胺 以 二氯甲烷 为溶剂， 反应 5.0h， 以60%的产率得到2,3-bis(N,N-diethylaminomethyl)-5,7-bis(2-thienyl)thieno[3,4-b]pyrazine
  参考文献：
  名称：

  Synthesis and Characterization of Thieno[3,4-b]pyrazine-Based Terthienyls: Tunable Precursors for Low Band Gap Conjugated Materials

  摘要：

  Synthetic methods have been developed for the preparation of new 2,3-dihalo- and 2,3-ditriflato-5,7-bis(2-thienyl)thieno[3,4-b]pyrazines. From these reactive intermediates, a variety of new 2,3-difunctionalized 5,7-bis(2-thienyl)-thieno[3,4-b]pyrazines have been produced as precursors to conjugated materials. Structural, electronic, and optical characterization of these new analogues illustrate the extent to which the electronic nature of the functional groups can be used to tune the electronic properties of these thieno[3,4-b]pyrazine-based terthienyl units.

  DOI：

  10.1021/jo400577q
• 作为产物：
  描述：

  3,4-二硝基-2,5-二噻吩-2-基噻吩 在 盐酸 、 tin(ll) chloride 作用下， 以 乙醇 为溶剂， 反应 78.0h， 生成 2,3-bis(bromomethyl)-5,7-bis(2-thienyl)thieno[3,4-b]pyrazine
  参考文献：
  名称：

  Synthesis and Characterization of Thieno[3,4-b]pyrazine-Based Terthienyls: Tunable Precursors for Low Band Gap Conjugated Materials

  摘要：

  Synthetic methods have been developed for the preparation of new 2,3-dihalo- and 2,3-ditriflato-5,7-bis(2-thienyl)thieno[3,4-b]pyrazines. From these reactive intermediates, a variety of new 2,3-difunctionalized 5,7-bis(2-thienyl)-thieno[3,4-b]pyrazines have been produced as precursors to conjugated materials. Structural, electronic, and optical characterization of these new analogues illustrate the extent to which the electronic nature of the functional groups can be used to tune the electronic properties of these thieno[3,4-b]pyrazine-based terthienyl units.

  DOI：

  10.1021/jo400577q