1,2-bis(2'-formyl-3',5'-dimethyl-4'-pyrrolyl)acetylene | 1266553-23-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-bis(2'-formyl-3',5'-dimethyl-4'-pyrrolyl)acetylene
• CAS: 1266553-23-4
• 化学式: C₁₆H₁₆N₂O₂
• 分子量: 268.315
• InChiKey: WVHNAWKTPGMHKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  65.72
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2,4-二甲基-3-乙基吡咯 、 1,2-bis(2'-formyl-3',5'-dimethyl-4'-pyrrolyl)acetylene 在 氢溴酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以42%的产率得到bis(2,4,7,9-tetramethyl-8-ethyldipyrrolylmethen-3-yl)acetylene dihydrobromide
  参考文献：
  名称：

  Synthesis and spectral properties of new 3,3’-bis(dipyrrolylmethene) with acetylene spacer

  摘要：

  Bis(2,4,7,9-tetramethyl-8-ethyldipyrrolylmethen-3-yl)acetylene dihydrobromide (H2L center dot 2HBr), new bis(dipyrrolylmethene), in whose molecule dipyrrolylmethene domains were connected through 3,3'-carbon atoms of internal pyrrole nuclei by acetylene spacer, were synthesized by original procedure. The compound was characterized by element analysis, IR, H-1 NMR, and electronic spectroscopy. The comparative analysis of spectral properties shows the reduction of the basicity of H2L ligand in comparison with the structural analogs, which contain internal methylene spacer. The quantum-chemical simulation showed that the rigid acetylene spacer gives linear structure to the H2L molecule in contrast to the spiral-shaped geometry of structural analogs with -CH2- spacer.

  DOI：

  10.1134/s107036321011023x
• 作为产物：
  描述：

  2-formyl-4-[(trimethylsilyl)ethynyl]-3,5-dimethylpyrrole 在 copper(l) iodide 、 dichlorobis(triphenylphosphine)palladium(II) 、 四丁基氟化铵 、 二乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 1,2-bis(2'-formyl-3',5'-dimethyl-4'-pyrrolyl)acetylene
  参考文献：
  名称：

  Synthesis and spectral properties of new 3,3’-bis(dipyrrolylmethene) with acetylene spacer

  摘要：

  Bis(2,4,7,9-tetramethyl-8-ethyldipyrrolylmethen-3-yl)acetylene dihydrobromide (H2L center dot 2HBr), new bis(dipyrrolylmethene), in whose molecule dipyrrolylmethene domains were connected through 3,3'-carbon atoms of internal pyrrole nuclei by acetylene spacer, were synthesized by original procedure. The compound was characterized by element analysis, IR, H-1 NMR, and electronic spectroscopy. The comparative analysis of spectral properties shows the reduction of the basicity of H2L ligand in comparison with the structural analogs, which contain internal methylene spacer. The quantum-chemical simulation showed that the rigid acetylene spacer gives linear structure to the H2L molecule in contrast to the spiral-shaped geometry of structural analogs with -CH2- spacer.

  DOI：

  10.1134/s107036321011023x