4,4'-(1,2-ethanediyl)bis[3,5-dimethylbis(ethyl)ester]-1H-pyrrole-2-carboxylate | 313054-95-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 4,4'-(1,2-ethanediyl)bis[3,5-dimethylbis(ethyl)ester]-1H-pyrrole-2-carboxylate
• 英文别名: ethyl 4-[2-(5-ethoxycarbonyl-2,4-dimethyl-1H-pyrrol-3-yl)ethyl]-3,5-dimethyl-1H-pyrrole-2-carboxylate
• CAS: 313054-95-4
• 化学式: C₂₀H₂₈N₂O₄
• 分子量: 360.453
• InChiKey: GAQKBGUDXMKNTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  84.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,4'-(1,2-ethanediyl)bis[3,5-dimethylbis(ethyl)ester]-1H-pyrrole-2-carboxylate 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 苯甲醇 为溶剂， 209.0 ℃ 、101.33 kPa 条件下， 反应 3.0h， 生成 bis(5-carboxyl-2,4-dimethyl-pyrrole-3-yl)-ethane
  参考文献：
  名称：

  Double-Helical Dinuclear Bis(dipyrromethene) Complexes Formed by Self-Assembly

  摘要：

  Bis(dipyrromethene) ligands linked by an alkyl spacer between beta and beta' positions are shown to give helical dimers or monomers, dependent upon the length of the alkyl linker, upon complexation. Ligands consisting of methylene, ethylene, and propylene linkers -(CH2)(n)- (n = 1, 2, and 3) give helical dimers, while longer linking chains (n = 4, 5, or 6) give monomers or mixtures of dimers and monomers. X-ray crystal structures of the dimeric zinc complexes (n = 1, 2, and 3) reveal that the angles between dipyrromethene planes and the extent of helicity in the complexes differ as the length of the linker varies. The extent of helicity was assessed and found to be dependent upon the length and, specifically, the conformational preferences of the alkyl spacer unit. The presence of an ethylene linker gave complexes of greatest helicity. The use of a methylene spacer gave less helical structures upon complexation, while propylene spacers gave only slightly helical complexes. Our studies identify the crucial importance that the conformational preferences of the beta-beta' alkyl spacer group plays in the coordination algorithm of self-assembly to form dipyrromethene based complexes.

  DOI：

  10.1021/jo000886p
• 作为产物：
  描述：

  3,5-二甲基-1H-吡咯-2-甲酸乙酯 在 sodium tetrahydroborate 、 三氟化硼乙醚 、 四氯化锡 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 12.25h， 生成 4,4'-(1,2-ethanediyl)bis[3,5-dimethylbis(ethyl)ester]-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  Double-Helical Dinuclear Bis(dipyrromethene) Complexes Formed by Self-Assembly

  摘要：

  Bis(dipyrromethene) ligands linked by an alkyl spacer between beta and beta' positions are shown to give helical dimers or monomers, dependent upon the length of the alkyl linker, upon complexation. Ligands consisting of methylene, ethylene, and propylene linkers -(CH2)(n)- (n = 1, 2, and 3) give helical dimers, while longer linking chains (n = 4, 5, or 6) give monomers or mixtures of dimers and monomers. X-ray crystal structures of the dimeric zinc complexes (n = 1, 2, and 3) reveal that the angles between dipyrromethene planes and the extent of helicity in the complexes differ as the length of the linker varies. The extent of helicity was assessed and found to be dependent upon the length and, specifically, the conformational preferences of the alkyl spacer unit. The presence of an ethylene linker gave complexes of greatest helicity. The use of a methylene spacer gave less helical structures upon complexation, while propylene spacers gave only slightly helical complexes. Our studies identify the crucial importance that the conformational preferences of the beta-beta' alkyl spacer group plays in the coordination algorithm of self-assembly to form dipyrromethene based complexes.

  DOI：

  10.1021/jo000886p