5-(2-(2-((4'-((2-(2-azidoethoxy)ethoxy)methyl)-[2,2'-bi(1,3-dithiolylidene)]-4-yl)methoxy)ethoxy)ethoxy)isophthalic acid | 1054534-92-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(2-(2-((4'-((2-(2-azidoethoxy)ethoxy)methyl)-[2,2'-bi(1,3-dithiolylidene)]-4-yl)methoxy)ethoxy)ethoxy)isophthalic acid
• CAS: 1054534-92-7
• 化学式: C₂₄H₂₇N₃O₉S₄
• 分子量: 629.757
• InChiKey: NLWFRQLPIFATHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.61
• 重原子数：
  40.0
• 可旋转键数：
  19.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  169.51
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  5-(prop-2-yn-1-yloxy)isophthalic acid 、 5-(2-(2-((4'-((2-(2-azidoethoxy)ethoxy)methyl)-[2,2'-bi(1,3-dithiolylidene)]-4-yl)methoxy)ethoxy)ethoxy)isophthalic acid 、 α-环糊精 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 48.0h， 以23%的产率得到
  参考文献：
  名称：

  A Redox-Switchable α-Cyclodextrin-Based [2]Rotaxane

  摘要：

  A bistable [2]rotaxane comprising an alpha-cyclodextrin (alpha-CD) ring and a dumbbell component containing a redox-active tetrathiafulvalene (TTF) ring system within its rod section has been synthesized using the Cu(I)-catalyzed azide-alkyne cycloaddition, and the redox-driven movements of the alpha-CD ring between the TTF and newly formed triazole ring systems have been elucidated. Microcalorimetric titrations on model complexes suggested that the alpha-CD ring prefers to reside on the TTF rather than on the triazole ring system by at least an order of magnitude. The fact that this situation does pertain in the bistable [2]rotaxane has not only been established quantitatively by electrochemical experiments and backed up by spectroscopic and chiroptical measurements but also been confirmed semiquantitatively by the recording of numerous cyclic voltammograms which point, along with the use of redox-active chemical reagents, to a mechanism of switching that involves the oxidation of the neutral TTF ring system to either its radical cationic (TTF(center dot+)) or dicationic (TTF(2+)) Counterparts, whereupon the alpha-CD ring, moves along the dumbbell to encircle the triazole ring system. Since redox control by both chemical and electrochemical means is reversible. the switching by the bistable [2]rotaxane can be reversed on reduction of the TTF(center dot+) or TTF(2+) back to being a neutral TTF.

  DOI：

  10.1021/ja8036146
• 作为产物：
  描述：

  dimethyl 5-(2-(2-((4'-((2-(2-azidoethoxy)ethoxy)methyl)-[2,2'-bi(1,3-dithiolylidene)]-4-yl)methoxy)ethoxy)ethoxy)isophthalate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以78%的产率得到5-(2-(2-((4'-((2-(2-azidoethoxy)ethoxy)methyl)-[2,2'-bi(1,3-dithiolylidene)]-4-yl)methoxy)ethoxy)ethoxy)isophthalic acid
  参考文献：
  名称：

  A Redox-Switchable α-Cyclodextrin-Based [2]Rotaxane

  摘要：

  A bistable [2]rotaxane comprising an alpha-cyclodextrin (alpha-CD) ring and a dumbbell component containing a redox-active tetrathiafulvalene (TTF) ring system within its rod section has been synthesized using the Cu(I)-catalyzed azide-alkyne cycloaddition, and the redox-driven movements of the alpha-CD ring between the TTF and newly formed triazole ring systems have been elucidated. Microcalorimetric titrations on model complexes suggested that the alpha-CD ring prefers to reside on the TTF rather than on the triazole ring system by at least an order of magnitude. The fact that this situation does pertain in the bistable [2]rotaxane has not only been established quantitatively by electrochemical experiments and backed up by spectroscopic and chiroptical measurements but also been confirmed semiquantitatively by the recording of numerous cyclic voltammograms which point, along with the use of redox-active chemical reagents, to a mechanism of switching that involves the oxidation of the neutral TTF ring system to either its radical cationic (TTF(center dot+)) or dicationic (TTF(2+)) Counterparts, whereupon the alpha-CD ring, moves along the dumbbell to encircle the triazole ring system. Since redox control by both chemical and electrochemical means is reversible. the switching by the bistable [2]rotaxane can be reversed on reduction of the TTF(center dot+) or TTF(2+) back to being a neutral TTF.

  DOI：

  10.1021/ja8036146