N,N'-((ethyne-1,2-diylbis(4,1-phenylene))bis(methylene))bis(2-(5,8-di-tert-butyl-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)acetamide) | 1381949-74-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: N,N'-((ethyne-1,2-diylbis(4,1-phenylene))bis(methylene))bis(2-(5,8-di-tert-butyl-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)acetamide)
• 英文别名: 2-(5,8-ditert-butyl-1,3-dioxobenzo[de]isoquinolin-2-yl)-N-[[4-[2-[4-[[[2-(5,8-ditert-butyl-1,3-dioxobenzo[de]isoquinolin-2-yl)acetyl]amino]methyl]phenyl]ethynyl]phenyl]methyl]acetamide
• CAS: 1381949-74-1
• 化学式: C₆₀H₆₂N₄O₆
• 分子量: 935.175
• InChiKey: PDBAUOYRENWIOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.8
• 重原子数：
  70
• 可旋转键数：
  14
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  133
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,4-苯二甲胺 、 N,N'-((ethyne-1,2-diylbis(4,1-phenylene))bis(methylene))bis(2-(5,8-di-tert-butyl-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)acetamide) 、 间苯二甲酰氯 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 20.0h， 以6%的产率得到[2]-(1,4,7,14,17,20-hexaaza-2,6,15,19-tetraoxo-3,5,9,12,16,18,22,25-tetrabenzocyclohexacosane)-N,N'-((ethyne-1,2-diylbis(4,1-phenylene))bis(methylene))bis(2-(5,8-di-tert-butyl-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)acetamide)
  参考文献：
  名称：

  Degenerate Molecular Shuttles with Flexible and Rigid Spacers

  摘要：

  The preparation and dynamic behavior of degenerate rotaxane molecular shuttles are described in which a benzylic amide macrocycle moves back and forth between two naphthalimide-glycine units along a diphenylethyne spacer or an aliphatic spacer consisting of a C-9, C-12, or C-26 alkyl chain. Subtle differences in the H-1 NMR spectra of the rotaxanes can be related to the presence of conformers in which the macrocycle interacts simultaneously with both glycines, especially in the case of the C-9 spacer. The kinetic data of the shuttling behavior in the C-26 rotaxane were obtained from dynamic NMR spectroscopy. The Eyring activation parameters were found to be Delta H-double dagger = 10 +/- 1 kcal mol(-1), Delta S-double dagger = -6.5 +/- 2.0 cal mol(-1) K-1, Delta G(298)(double dagger) = 11.9 +/- 0.2 kcal mol(-1). For the systems with the shorter spacers, the shuttling rates were higher. Also in the diphenylethyne, rotaxane shuttling is rapid on the NMR time scale, indicating that the rigid unit does not impose a large barrier to the translocation of the macrocycle.

  DOI：

  10.1021/jo300907r
• 作为产物：
  描述：

  4-碘苄胺盐酸盐 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 25.0h， 生成 N,N'-((ethyne-1,2-diylbis(4,1-phenylene))bis(methylene))bis(2-(5,8-di-tert-butyl-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)acetamide)
  参考文献：
  名称：

  Degenerate Molecular Shuttles with Flexible and Rigid Spacers

  摘要：

  The preparation and dynamic behavior of degenerate rotaxane molecular shuttles are described in which a benzylic amide macrocycle moves back and forth between two naphthalimide-glycine units along a diphenylethyne spacer or an aliphatic spacer consisting of a C-9, C-12, or C-26 alkyl chain. Subtle differences in the H-1 NMR spectra of the rotaxanes can be related to the presence of conformers in which the macrocycle interacts simultaneously with both glycines, especially in the case of the C-9 spacer. The kinetic data of the shuttling behavior in the C-26 rotaxane were obtained from dynamic NMR spectroscopy. The Eyring activation parameters were found to be Delta H-double dagger = 10 +/- 1 kcal mol(-1), Delta S-double dagger = -6.5 +/- 2.0 cal mol(-1) K-1, Delta G(298)(double dagger) = 11.9 +/- 0.2 kcal mol(-1). For the systems with the shorter spacers, the shuttling rates were higher. Also in the diphenylethyne, rotaxane shuttling is rapid on the NMR time scale, indicating that the rigid unit does not impose a large barrier to the translocation of the macrocycle.

  DOI：

  10.1021/jo300907r

文献信息

• Degenerate Molecular Shuttles with Flexible and Rigid Spacers
  作者：D. Deniz Günbaş、Albert M. Brouwer

  DOI：10.1021/jo300907r

  日期：2012.7.6

  The preparation and dynamic behavior of degenerate rotaxane molecular shuttles are described in which a benzylic amide macrocycle moves back and forth between two naphthalimide-glycine units along a diphenylethyne spacer or an aliphatic spacer consisting of a C-9, C-12, or C-26 alkyl chain. Subtle differences in the H-1 NMR spectra of the rotaxanes can be related to the presence of conformers in which the macrocycle interacts simultaneously with both glycines, especially in the case of the C-9 spacer. The kinetic data of the shuttling behavior in the C-26 rotaxane were obtained from dynamic NMR spectroscopy. The Eyring activation parameters were found to be Delta H-double dagger = 10 +/- 1 kcal mol(-1), Delta S-double dagger = -6.5 +/- 2.0 cal mol(-1) K-1, Delta G(298)(double dagger) = 11.9 +/- 0.2 kcal mol(-1). For the systems with the shorter spacers, the shuttling rates were higher. Also in the diphenylethyne, rotaxane shuttling is rapid on the NMR time scale, indicating that the rigid unit does not impose a large barrier to the translocation of the macrocycle.