2-(carboxymethyl)-5,8-di-tert-butyl-benzo[de]isoquinoline-1,3-dione | 1226910-36-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-(carboxymethyl)-5,8-di-tert-butyl-benzo[de]isoquinoline-1,3-dione
• 英文别名: 2-(acetic acid)-5-8-di-tert-butyl-benzo[de]isoquinoline-1,3-dione；2-(acetic acid)-5,8-ditert-butyl-benzo[de]isoquinoline-1,3-dione；2-(5,8-Ditert-butyl-1,3-dioxobenzo[de]isoquinolin-2-yl)acetic acid
• CAS: 1226910-36-6
• 化学式: C₂₂H₂₅NO₄
• 分子量: 367.445
• InChiKey: VJJUGYYXEQFGCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  74.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(carboxymethyl)-5,8-di-tert-butyl-benzo[de]isoquinoline-1,3-dione 、 hexacosane-1,26-diamine 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以60%的产率得到N,N'-(hexacosane-1,26-diyl)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：

  2,5-di-tert-butylacenaphthylic anhydride 、 聚甘氨酸 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以70%的产率得到2-(carboxymethyl)-5,8-di-tert-butyl-benzo[de]isoquinoline-1,3-dione
  参考文献：
  名称：

  Energy landscape of a hydrogen-bonded non-degenerate molecular shuttle

  摘要：

  在 CDCl3 中，温度介于 250 至 330 K 之间的轮烷 1 有两种共构型。热力学参数显示，两种形态之间存在较强的焓熵补偿和不可忽略的热容量差。

  DOI：

  10.1039/b926868e

文献信息

• Solvatochromic rotaxane molecular shuttles
  作者：Duygu Deniz Günbaş、Leszek Zalewski、Albert M. Brouwer

  DOI：10.1039/c0cc05755j

  日期：——

  A strongly fluorescent bistable rotaxane is described in which the relative position of the macrocyclic ring with respect to a solvatochromic fluorophore gives a strong response in the spectral domain.

  描述了一种强荧光双稳态轮烷，其中大环相对于溶色荧光团的相对位置会在光谱域产生强烈反应。