1,3-bis[7,7-di(pyrrol-2-yl)octyloxy]-5-methylbenzene | 560094-03-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,3-bis[7,7-di(pyrrol-2-yl)octyloxy]-5-methylbenzene
• CAS: 560094-03-3
• 化学式: C₃₉H₅₂N₄O₂
• 分子量: 608.867
• InChiKey: HSRUURCALMSURH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.98
• 重原子数：
  45.0
• 可旋转键数：
  20.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  81.62
• 氢给体数：
  4.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  丙酮 、 1,3-bis[7,7-di(pyrrol-2-yl)octyloxy]-5-methylbenzene 在 三氟化硼乙醚 作用下， 反应 0.33h， 以8%的产率得到1,11,21,26,26,35,35-heptamethyl-8,14-dioxa-40,41,42,43-tetrazaheptacyclo[19.9.9.19,13.122,25.127,30.131,34.136,39]tetratetraconta-9(44),10,12,22,24,27,29,31,33,36,38-undecaene
  参考文献：
  名称：

  Single Side Strapping:  A New Approach to Fine Tuning the Anion Recognition Properties of Calix[4]pyrroles

  摘要：

  Three calix[4]pyrroles bearing m-orcinol-derived diether straps of different lengths on one side of the tetrapyrrolic core have been synthesized and characterized. Structural information for an analogous diester bridged strapped system reported previously (Yoon, D. W.; Hwang, H.; Lee, C. H. Angew. Chem., Int. Ed. Engl. 2002, 41, 1757-1759) is also provided as are bromide and chloride anion affinities for all four systems determined by Isothermal Titration Calorimetry (ITC) in acetonitrile. Although both sets of the strapped calix[4]pyrroles displayed enhanced affinities for chloride and bromide anion, differences were seen among the various receptors that support the conclusion that the anion binding ability of calixpyrrole- type systems can be effectively tuned by modifying the length and nature of the bridging straps. In the specific case of the diether systems, the largest chloride affinity was seen with the shortest strap, whereas the largest affinity for bromide anion was recorded in the case of the longest strap. On the basis of these findings, as well as supporting H-1 NMR spectroscopic studies, it is postulated that not only cavity size per se, but also the ability of the aryl portion of the strap to serve as a CH hydrogen bond donor site are important in regulating the observed anion affinities.

  DOI：

  10.1021/ja029175u
• 作为产物：
  描述：

  8-溴辛烷-2-酮 在 potassium carbonate 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.84h， 生成 1,3-bis[7,7-di(pyrrol-2-yl)octyloxy]-5-methylbenzene
  参考文献：
  名称：

  Single Side Strapping:  A New Approach to Fine Tuning the Anion Recognition Properties of Calix[4]pyrroles

  摘要：

  Three calix[4]pyrroles bearing m-orcinol-derived diether straps of different lengths on one side of the tetrapyrrolic core have been synthesized and characterized. Structural information for an analogous diester bridged strapped system reported previously (Yoon, D. W.; Hwang, H.; Lee, C. H. Angew. Chem., Int. Ed. Engl. 2002, 41, 1757-1759) is also provided as are bromide and chloride anion affinities for all four systems determined by Isothermal Titration Calorimetry (ITC) in acetonitrile. Although both sets of the strapped calix[4]pyrroles displayed enhanced affinities for chloride and bromide anion, differences were seen among the various receptors that support the conclusion that the anion binding ability of calixpyrrole- type systems can be effectively tuned by modifying the length and nature of the bridging straps. In the specific case of the diether systems, the largest chloride affinity was seen with the shortest strap, whereas the largest affinity for bromide anion was recorded in the case of the longest strap. On the basis of these findings, as well as supporting H-1 NMR spectroscopic studies, it is postulated that not only cavity size per se, but also the ability of the aryl portion of the strap to serve as a CH hydrogen bond donor site are important in regulating the observed anion affinities.

  DOI：

  10.1021/ja029175u