1,2,3,4-tetra(pyridin-4-yl)cyclobutane | 62415-98-9

• 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: 1,2,3,4-tetra(pyridin-4-yl)cyclobutane
• 英文别名: r-1,c-2,t-3,t-4-Tetra(4-pyridyl)cyclobutane；rtct-1,2,3,4-tetrakis(4-pyridyl)cyclobutane；1r,2t,3c,4t-tetrakis(4-pyridyl)cyclobutane；rtct-tetrakis(4-pyridyl)cyclobutane；rtct-tpcb
• CAS: 62415-98-9；73078-76-9；82650-04-2
• 化学式: C₂₄H₂₀N₄
• 分子量: 364.45
• InChiKey: AECYBGVNRKERAQ-SWIJEOLNSA-N

物化性质

• 熔点：
  234 °C(Solv: dichloromethane (75-09-2); heptane (142-82-5))
• 沸点：
  505.3±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)：
  4.72
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  51.56
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetra(pyridin-4-yl)cyclobutane 、 potassium n-butoxide 生成 tetrakis(4-pyridyl)cyclobutane
  参考文献：
  名称：

  HORNER, M.;HUENIG, S., LIEBIGS ANN. CHEM., 1982, N 6, 1183-1210

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2-二(4-吡啶基)乙烯 以 水 为溶剂， 生成 1,2,3,4-tetra(pyridin-4-yl)cyclobutane
  参考文献：
  名称：

  Combining topochemical [2+2] photoreactions and hydrothermal isomerisation for the regioselective and quantitative preparation ofrtct-pyridylcyclobutanes

  摘要：

  通过将固态[2+2]光反应与在水热条件下由路易斯酸或布朗斯酸促成的受控异构化相结合，实现了一种非光化学途径用于选择性和定量制备反式-吡啶基环丁烷异构体的方法。

  DOI：

  10.1039/c2nj20855e

文献信息

• Solid-State Photochemical [2+2] Cycloaddition in a Hydrogen-Bonded Metal Complex Containing Several Parallel and Crisscross CC bonds
  作者：Abdul Malik Puthan Peedikakkal、Jagadese J. Vittal

  DOI：10.1002/chem.200701494

  日期：2008.6.9

  One-dimensional hydrogen-bonded complex [Zn(bpe)(2)(H(2)O)(4)](NO(3))(2).8/3 H(2)O.2/3 bpe (1, bpe=4,4'-bipyridylethylene) containing coordination complex cations [Zn(bpe)(2)(H(2)O)(4)](2+) with parallel and crisscross double bonds undergoes photochemical [2+2] cycloaddition in the solid state and produces tetrakis(4-pyridyl)cyclobutane (tpcb) in up to 100 % yield with rctt-tpcb (2a) as major and rtct-tpcb

  一维氢键络合物[Zn（bpe）（2）（H（2）O）（4）]（NO（3））（2）.8 / 3 H（2）O.2 / 3 bpe（ 1，带有配位和纵横双键的配位络合物阳离子[Zn（bpe）（2）（H（2）O）（4）]（2+）的光配体[2 + 2]在固态下进行环加成，并以rctt-tpcb（2a）作为主要产物和rtct-tpcb（2b）作为次要产物，以高达100％的产率生产四（4-吡啶基）环丁烷（tpcb）。具有C = C键的交叉构象的bpe配体在进行光二聚化之前似乎经历了踏板状运动。将单晶研磨成粉末可加快bpe配体中纵横交联的烯烃的踏板运动，使其平行排列，并定量提供rctt-环丁烷立体异构体2a。此外，地面1的100％光二聚化表明，游离的bpe配体
• Template-stereocontrolled [2 + 2] photoreactions directed by surface recognition on hydrophilic functionalized carbon materials
  作者：Gabriela Ortega、Alexander Briceño

  DOI：10.1039/c7ce01090g

  日期：——

  Supramolecular assistance of the regioselective synthesis of single dimers from [2 + 2] photoreactions surface-directed by multivalent H-bonding exo-templates based on hydrophilic carbon materials (HCMs) is highlighted for the first time. Supramolecular photochemistry of stilbenes assisted by either functionalized carbon nanotubes or sub-microspheres afforded a single rtct-isomer after two consecutive

  由基于亲水性碳材料（HCM）的多价H键外显子模板表面定向的[2 + 2]光反应区域选择性合成单二聚体的超分子辅助首次得到强调。在溶液中连续两个步骤（紫外线照射和水热异构化）后，由功能化的碳纳米管或亚微球辅助的对苯二甲酸酯的超分子光化学提供了一个单一的rtct-异构体。碳球显示出以中等至定量产率介导4-肉桂酸衍生物二聚化的能力。该结果可以通过溶液或通过碳球/肉桂衍生物组件的机械化学研磨辅助。由于表面上存在–COOH和–OH基团以及有效的碳模板：底物比率，因此将此类纳米材料的结构模板特征作为表面识别过程的函数进行了讨论。
• [2+2] Photodimerization of bispyridylethylenes by a controlled shift of the protonation equilibrium
  作者：Shinji Yamada、Momoko Kusafuka、Mai Sugawara

  DOI：10.1016/j.tetlet.2013.05.075

  日期：2013.7

  Irradiation of trans-4,4'-bispyridylethylene in the presence of I equiv of concd HCl produced a syn dimer with high selectivity, whereas irradiation in the presence of more than 2 equiv of concd HCl or in the absence of HCl gave a mixture of dimers and by-products with much lower selectivity. This indicated that a suitable amount of acid served as a catalyst for the [2+2] photodimerization of BPEs through cation-pi interactions between the pyridinium and pyridine rings. (C) 2013 Elsevier Ltd. All rights reserved.
• Horner, Michael; Huenig, Siegfried, Liebigs Annalen der Chemie, 1982, # 6, p. 1183 - 1210
  作者：Horner, Michael、Huenig, Siegfried

  DOI：——

  日期：——
• Metal−Organic Frameworks Containing a Tetrapyridylcyclobutane Ligand Derived from Isomerization Reaction
  作者：Abdul Malik Puthan Peedikakkal、Charlene Shi Yun Peh、Lip Lin Koh、Jagadese J. Vittal

  DOI：10.1021/ic100853h

  日期：2010.8.2

  The rctt isomer of tetrapyridylcyclobutane prepared from the solid-state [2 + 2.] cycloaddition reaction of [bpeH(2)]center dot 2CF(3)CO(2) [bpe = 1,2-bis(4-pyridyl)ethene] undergoes isomerization reaction to the rtct isomer in 100% yield, and this tetrahedral tetrapyridyl ligand forms two metal organic frameworks having ptt and pts topology.