(61E)-3,5,7,9-tetrakis(perfluorophenyl)-82,85-dihydro-11H,21H,41H,62H,81H-1,2(2,3),4,6,8(2,5)-pentapyrrolacyclononaphane | 1510006-37-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四吡咯及其衍生物
• 英文名称: (61E)-3,5,7,9-tetrakis(perfluorophenyl)-82,85-dihydro-11H,21H,41H,62H,81H-1,2(2,3),4,6,8(2,5)-pentapyrrolacyclononaphane
• CAS: 1510006-37-7
• 化学式: C₄₈H₁₅F₂₀N₅
• 分子量: 1041.65
• InChiKey: WORPNYQYHKOPAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.86
• 重原子数：
  73.0
• 可旋转键数：
  4.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.02
• 拓扑面积：
  75.52
• 氢给体数：
  4.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (61E)-3,5,7,9-tetrakis(perfluorophenyl)-82,85-dihydro-11H,21H,41H,62H,81H-1,2(2,3),4,6,8(2,5)-pentapyrrolacyclononaphane 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以90%的产率得到
  参考文献：
  名称：

  Macrocycle Contraction and Expansion of a Dihydrosapphyrin Isomer

  摘要：

  Cyclization of a pentapyrrane with two terminal beta-linked pyrroles afforded a dihydrosapphyrin isomer (1) with the pyrroles linked in a unique beta,alpha-alpha,beta mode, which was rather reactive, and thus it readily underwent a ring-contracted rearrangement to a pyrrolyl norrole (2), and succeeding ring expansion to a terpyrrole-containing isosmaragdyrin analogue (4). 1, 2, and 4 contain the internal ring pathways with a minimum of 17, 15, and 16 atoms, respectively. 1, 2, and 4 are almost nonfluorescent, whereas the complex of 2 with Zn2+ shows a distinct NIR emission peak at 741 nm. The unprecedented pyrrole transformation chemistry by confusion approach is illustrated.

  DOI：

  10.1021/ja4112644
• 作为产物：
  描述：

  2,5-bis((perfluorophenyl)(5-((perfluorophenyl)(1H-pyrrol-3-yl)methyl)-1H-pyrrol-2-yl)methyl)-1H-pyrrole 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以7%的产率得到(61E)-3,5,7,9-tetrakis(perfluorophenyl)-82,85-dihydro-11H,21H,41H,62H,81H-1,2(2,3),4,6,8(2,5)-pentapyrrolacyclononaphane
  参考文献：
  名称：

  Macrocycle Contraction and Expansion of a Dihydrosapphyrin Isomer

  摘要：

  Cyclization of a pentapyrrane with two terminal beta-linked pyrroles afforded a dihydrosapphyrin isomer (1) with the pyrroles linked in a unique beta,alpha-alpha,beta mode, which was rather reactive, and thus it readily underwent a ring-contracted rearrangement to a pyrrolyl norrole (2), and succeeding ring expansion to a terpyrrole-containing isosmaragdyrin analogue (4). 1, 2, and 4 contain the internal ring pathways with a minimum of 17, 15, and 16 atoms, respectively. 1, 2, and 4 are almost nonfluorescent, whereas the complex of 2 with Zn2+ shows a distinct NIR emission peak at 741 nm. The unprecedented pyrrole transformation chemistry by confusion approach is illustrated.

  DOI：

  10.1021/ja4112644