2-{4-(2-{2-[2-(tetrahydropyranyl-2-oxy)ethoxy]ethoxy}ethylthio)-5-methylthio-1,3-dithiol-2-ylidene}-5-{2-(2-[2-(tetrahydropyranyl-2-oxy)ethoxy]ethoxy)ethyl}-(1,3)-dithiolo[4,5-c]pyrrole | 929557-83-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-{4-(2-{2-[2-(tetrahydropyranyl-2-oxy)ethoxy]ethoxy}ethylthio)-5-methylthio-1,3-dithiol-2-ylidene}-5-{2-(2-[2-(tetrahydropyranyl-2-oxy)ethoxy]ethoxy)ethyl}-(1,3)-dithiolo[4,5-c]pyrrole
• 英文别名: 2-[4-Methylsulfanyl-5-[2-[2-[2-(oxan-2-yloxy)ethoxy]ethoxy]ethylsulfanyl]-1,3-dithiol-2-ylidene]-5-[2-[2-[2-(oxan-2-yloxy)ethoxy]ethoxy]ethyl]-[1,3]dithiolo[4,5-c]pyrrole
• CAS: 929557-83-5
• 化学式: C₃₁H₄₇NO₈S₆
• 分子量: 754.112
• InChiKey: DGRJRSGSBDBIPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  46
• 可旋转键数：
  22
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  231
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  2-{4-(2-{2-[2-(tetrahydropyranyl-2-oxy)ethoxy]ethoxy}ethylthio)-5-methylthio-1,3-dithiol-2-ylidene}-5-{2-(2-[2-(tetrahydropyranyl-2-oxy)ethoxy]ethoxy)ethyl}-(1,3)-dithiolo[4,5-c]pyrrole 在 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 24.0h， 以79%的产率得到2-{4-(2-[2-(hydroxyethoxy)ethoxy]ethylthio)-5-methylthio-1,3-dithiol-2-ylidene}-5-{2-[2-(hydroxyethoxy)ethoxy]ethyl}-(1,3)-dithiolo[4,5-c]pyrrole
  参考文献：
  名称：

  Binding Studies between Triethylene Glycol-Substituted Monopyrrolotetrathiafulvalene Derivatives and Cyclobis(paraquat-p-phenylene)

  摘要：

  The synthesis of several pi-electron-donating monopyrrolotetrathiafulvalene (MPTTF) derivatives, which conceptually can be divided into three classes containing none, one, or two triethylene glycol (TEG) substituents, is described. In all cases, the complexation between the pi-electron donating MPTTF unit and the pi-electron-deficient tetracationic cyclophane cyclobis(paraquat-p-phenylene) (CBPQT(4+)) has been investigated using UV-vis dilution techniques. The results reveal that the strength of the binding between MPTTF derivatives and CBPQT(4+) is directly correlated to the pi-electron donating properties of the MPTTF derivatives. However, the pi-electron-donating properties of the MPTTF derivatives is not the only factor of importance. The results enclosed in the present studies demonstrate that the TEG substituents assist the complexation process most likely on account of their capacity to participate in [C-H center dot center dot center dot O] hydrogen bonding interactions with some of the alpha-CH protons in the bipyridinium units of CBPQT(4+) and the stabilizing effect that attachment of one or two TEG substituents to the MPTTF unit exerts upon complexation with CBPQT(4+) has been quantified to approximately 0.3 and 0.5 kcal mol(-1), respectively. These results serve to lay an extended foundation for the understanding of which buttons to push when it comes to improve the design of bistable molecular switches based on (MP)TTF and CBPQT(4+).

  DOI：

  10.1021/jo061962c
• 作为产物：
  描述：

  3-((5-(methylthio)-2-(5-tosyl-5H-[1,3]dithiolo[4,5-c]pyrrol-2-ylidene)-1,3-dithiol-4-yl)thio)propanenitrile 在 cesium hydroxide 、 sodium methylate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.33h， 生成 2-{4-(2-{2-[2-(tetrahydropyranyl-2-oxy)ethoxy]ethoxy}ethylthio)-5-methylthio-1,3-dithiol-2-ylidene}-5-{2-(2-[2-(tetrahydropyranyl-2-oxy)ethoxy]ethoxy)ethyl}-(1,3)-dithiolo[4,5-c]pyrrole
  参考文献：
  名称：

  Binding Studies between Triethylene Glycol-Substituted Monopyrrolotetrathiafulvalene Derivatives and Cyclobis(paraquat-p-phenylene)

  摘要：

  The synthesis of several pi-electron-donating monopyrrolotetrathiafulvalene (MPTTF) derivatives, which conceptually can be divided into three classes containing none, one, or two triethylene glycol (TEG) substituents, is described. In all cases, the complexation between the pi-electron donating MPTTF unit and the pi-electron-deficient tetracationic cyclophane cyclobis(paraquat-p-phenylene) (CBPQT(4+)) has been investigated using UV-vis dilution techniques. The results reveal that the strength of the binding between MPTTF derivatives and CBPQT(4+) is directly correlated to the pi-electron donating properties of the MPTTF derivatives. However, the pi-electron-donating properties of the MPTTF derivatives is not the only factor of importance. The results enclosed in the present studies demonstrate that the TEG substituents assist the complexation process most likely on account of their capacity to participate in [C-H center dot center dot center dot O] hydrogen bonding interactions with some of the alpha-CH protons in the bipyridinium units of CBPQT(4+) and the stabilizing effect that attachment of one or two TEG substituents to the MPTTF unit exerts upon complexation with CBPQT(4+) has been quantified to approximately 0.3 and 0.5 kcal mol(-1), respectively. These results serve to lay an extended foundation for the understanding of which buttons to push when it comes to improve the design of bistable molecular switches based on (MP)TTF and CBPQT(4+).

  DOI：

  10.1021/jo061962c