r-1,c-2,t-3,t-4-Tetra(2-pyridyl)cyclobutane | 73069-90-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: r-1,c-2,t-3,t-4-Tetra(2-pyridyl)cyclobutane
• 英文别名: 2-(2,3,4-Tripyridin-2-ylcyclobutyl)pyridine
• CAS: 73069-90-6
• 化学式: C₂₄H₂₀N₄
• 分子量: 364.45
• InChiKey: FFKLHTJYOABTKB-UHFFFAOYSA-N

物化性质

• 沸点：
  527.1±50.0 °C(Predicted)
• 密度：
  1.212±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,2-双吡啶基乙烯 以 乙醇 为溶剂， 反应 84.0h， 生成 r-1,c-2,t-3,t-4-Tetra(2-pyridyl)cyclobutane
  参考文献：
  名称：

  Comparison of Templating Abilities of Urea and Thioruea During Photodimerization of Bipyridylethyelene and Stilbazole Crystals

  摘要：

  AbstractPhotodimerization of cocrystals of four bispyridylethylenes and two stilbazoles with urea as a template in the solid state has been investigated following our success with thiourea. Four investigated olefins photodimerized quantitatively to a single dimer in the crystalline state only. The reactivity of urea–olefin crystals is understood on the basis of their packing arrangements in the crystalline state. In reactive crystals the adjacent reactive molecules are within 4.2 Å and parallel, whereas the unreactive ones have their adjacent molecules are farther than 4.6Å and nonparallel. Thus, with the knowledge of crystal packing the reactivity of urea–olefin crystals is predictable on the basis of Schmidt's topochemical postulates. The templating property of urea, similar to thiourea, derives from its ability to form hydrogen bonds with itself and the guest olefins. Despite the similarities in molecular structures of urea and thiourea their subtle electronic properties, yet to be fully understood, affect the crystal packing and consequently their reactivity in the crystalline state. Further work is needed to fully exploit the templating properties of urea.

  DOI：

  10.1111/php.12353

文献信息

• Self-assembly, concomitant photochemical processes, and improvement of the yield of [2 + 2] photoreactions from supramolecular arrays via mechanochemical assistance
  作者：Alexander Briceño、Dayana Leal、Gabriela Ortega、Graciela Díaz de Delgado、Edgar Ocando、Liz Cubillan

  DOI：10.1039/c3ce26752k

  日期：——

  Novel examples of self-assembly, structural transformations and concomitant photochemical processes from supramolecular ternary assemblies directed by charge-assisted hydrogen bonds are shown. In addition, mechanochemical assistance is also shown as a potential tool in order to improve the yield of [2 + 2] photoreactions in the solid state.

  展示了由电荷辅助氢键引导的超分子三元组装体中的自组装、新颖的结构转变及伴随的光化学过程。此外，还展示了机械化学辅助作为一种潜在工具，以提高固态[2 + 2]光反应的产率。
• A non-photochemical route for the regioselective preparation of rtct-pyridylcyclobutanes via hydrothermal isomerisation promoted by polymolybdates
  作者：Alexander Briceño、Aaron Fulgence、Yennifer Hill、Reinaldo Atencio

  DOI：10.1039/b801845f

  日期：——

  A novel approach for the regioselective preparation of rtct-tpcb (tpcb = tetrapyridylcyclobutanes) compounds promoted by polymolybdates under hydrothermal conditions is reported; these isomers are stabilised as counterions in inorganic–organic hybrid solids and are obtained in high to fair yield.

  报告了一种在水热条件下由多钼酸盐促进的区域选择性制备 rtct-tpcb（tpcb = 四吡啶基环丁烷）化合物的新方法；这些异构体作为反离子稳定在无机-有机杂化固体中，并以高产率甚至相当高的产率获得。
• Achieving a series of solid-state [2 + 2] cycloaddition reactions involving 1,2-bis(2-pyridyl)ethylene within halogen-bonded co-crystals
  作者：Max Andren、Eric Bosch、Herman R. Krueger、Ryan H. Groeneman

  DOI：10.1039/d4ce00097h

  日期：2024.3.5

  The solid-state [2 + 2] cycloaddition reaction of trans-1,2-bis(2-pyridyl)ethylene through both co-crystallization and mechanical grinding is reported. The photoreaction is achieved by using iodoperchlorobenzene as a molecular template. The co-crystal is sustained primarily by I⋯N halogen bonds and homogeneous face-to-face π–π stacking interactions. The combination of these non-covalent forces ultimately

  报道了反式-1,2-双(2-吡啶基)乙烯通过共结晶和机械研磨的固态[2+2]环加成反应。光反应是通过使用碘过氯苯作为分子模板来实现的。共晶主要由 I⋯N 卤素键和均匀的面对面 π-π 堆积相互作用维持。这些非共价力的组合最终将反应物置于适合光反应的位置。此外，还通过无溶剂机械研磨方法获得了一对光反应性固体，且产率相似。
• Azastilbenes. 2. Photodimerization
  作者：J. Vansant、S. Toppet、G. Smets、J. P. Declercq、G. Germain、M. Van Meerssche

  DOI：10.1021/jo01297a003

  日期：1980.4
• Comparison of Templating Abilities of Urea and Thioruea During Photodimerization of Bipyridylethyelene and Stilbazole Crystals
  作者：Balakrishna R. Bhogala、Burjor Captain、Vaidhyanathan Ramamurthy

  DOI：10.1111/php.12353

  日期：2015.5

  AbstractPhotodimerization of cocrystals of four bispyridylethylenes and two stilbazoles with urea as a template in the solid state has been investigated following our success with thiourea. Four investigated olefins photodimerized quantitatively to a single dimer in the crystalline state only. The reactivity of urea–olefin crystals is understood on the basis of their packing arrangements in the crystalline state. In reactive crystals the adjacent reactive molecules are within 4.2 Å and parallel, whereas the unreactive ones have their adjacent molecules are farther than 4.6Å and nonparallel. Thus, with the knowledge of crystal packing the reactivity of urea–olefin crystals is predictable on the basis of Schmidt's topochemical postulates. The templating property of urea, similar to thiourea, derives from its ability to form hydrogen bonds with itself and the guest olefins. Despite the similarities in molecular structures of urea and thiourea their subtle electronic properties, yet to be fully understood, affect the crystal packing and consequently their reactivity in the crystalline state. Further work is needed to fully exploit the templating properties of urea.