2-[4-(methylthio)-1,3-dithiol-2-ylidene]-5H-1,3-dithiolo[4,5-c]pyrrole | 848153-08-2

• 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-(methylthio)-1,3-dithiol-2-ylidene]-5H-1,3-dithiolo[4,5-c]pyrrole
• 英文别名: 2-(4-methylsulfanyl-1,3-dithiol-2-ylidene)-5H-[1,3]dithiolo[4,5-c]pyrrole
• CAS: 848153-08-2
• 化学式: C₉H₇NS₅
• 分子量: 289.491
• InChiKey: HQZYYTQBHUPRLJ-UHFFFAOYSA-N

物化性质

• 熔点：
  63.5-65 °C
• 沸点：
  379.5±42.0 °C(Predicted)
• 密度：
  1.69±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  142
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[4-(methylthio)-1,3-dithiol-2-ylidene]-5H-1,3-dithiolo[4,5-c]pyrrole 在 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-{4-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：

  5-tosyl-[1,3]dithiolo[4,5-c]pyrrol-2-one 在 cesium hydroxide 、 sodium methylate 、 亚磷酸三乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.83h， 生成 2-[4-(methylthio)-1,3-dithiol-2-ylidene]-5H-1,3-dithiolo[4,5-c]pyrrole
  参考文献：
  名称：

  磨练用于设备设置的两亲双稳态 [2] 轮烷类型

  摘要：

  为了响应分子电活性器件的要求，设计、合成和表征了两亲双稳态 [2] 轮烷形状的分子穿梭机。它包含一个疏水的四芳基甲烷和一个亲水的树枝状塞子和两个富含 π 电子的站——一个（单吡咯）四硫富瓦烯单元和一个 1,5-二氧萘部分——位于其哑铃部件的杆部分，可以作为识别四阳离子环芳环双（百草枯-对亚苯基）的位置。与先前报道的“慢速”两亲双稳态 [2] 轮烷相比，后者具有直接连接到（单吡咯并）四硫富瓦烯单元的 SMe 基团，这种“新的和改进的”双稳态 [2] 轮烷所连接的氢原子体积要小得多到（单吡咯）四硫富瓦烯单元。在比较两种双稳态 [2] 轮烷的物理性质时，（单吡咯并）四硫富瓦烯单元上取代基的这种看似微小的差异导致了深刻的变化。还制备了两种仅包含（单吡咯并）四硫富瓦烯单元的亲水性半哑铃化合物和一种仅在其杆部分包含 1,5-二氧萘部分的疏水性半哑铃化合物，并用于形成它们相应的环双（百草枯-对亚苯基）复合体。已经使用吸收和

  DOI：

  10.1002/ejoc.200400530

文献信息

• Binding Studies between Triethylene Glycol-Substituted Monopyrrolotetrathiafulvalene Derivatives and Cyclobis(paraquat-<i>p</i>-phenylene)
  作者：Sune Nygaard、Camilla N. Hansen、Jan O. Jeppesen

  DOI：10.1021/jo061962c

  日期：2007.3.1

  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+).
• Honing Up a Genre of Amphiphilic Bistable [2]Rotaxanes for Device Settings
  作者：Jan�O. Jeppesen、Sune Nygaard、Scott�A. Vignon、J.�Fraser Stoddart

  DOI：10.1002/ejoc.200400530

  日期：2005.1

  tetracationic cyclophane, cyclobis(paraquat-p-phenylene), to reside around. In contrast to a previously reported “slow” amphiphilic bistable [2]rotaxane, which has an SMe group attached directly to the (monopyrrolo)tetrathiafulvalene unit, this “new and improved” bistable [2]rotaxane has a much less bulky hydrogen atom attached to the (monopyrrolo)tetrathiafulvalene unit. This seemingly small difference in

  为了响应分子电活性器件的要求，设计、合成和表征了两亲双稳态 [2] 轮烷形状的分子穿梭机。它包含一个疏水的四芳基甲烷和一个亲水的树枝状塞子和两个富含 π 电子的站——一个（单吡咯）四硫富瓦烯单元和一个 1,5-二氧萘部分——位于其哑铃部件的杆部分，可以作为识别四阳离子环芳环双（百草枯-对亚苯基）的位置。与先前报道的“慢速”两亲双稳态 [2] 轮烷相比，后者具有直接连接到（单吡咯并）四硫富瓦烯单元的 SMe 基团，这种“新的和改进的”双稳态 [2] 轮烷所连接的氢原子体积要小得多到（单吡咯）四硫富瓦烯单元。在比较两种双稳态 [2] 轮烷的物理性质时，（单吡咯并）四硫富瓦烯单元上取代基的这种看似微小的差异导致了深刻的变化。还制备了两种仅包含（单吡咯并）四硫富瓦烯单元的亲水性半哑铃化合物和一种仅在其杆部分包含 1,5-二氧萘部分的疏水性半哑铃化合物，并用于形成它们相应的环双（百草枯-对亚苯基）复合体。已经使用吸收和