5,7,23,25-Tetrakis(brommethyl)-2,11,20,29-tetrakis(p-tolylsulfonyl)-2,11,20,29-tetraaza[3.3](1,3)(1,3)[3.3](4,6)(1,3)benzeno[3]phan | 156417-91-3

• 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: 5,7,23,25-Tetrakis(brommethyl)-2,11,20,29-tetrakis(p-tolylsulfonyl)-2,11,20,29-tetraaza[3.3](1,3)(1,3)[3.3](4,6)(1,3)benzeno[3]phan
• 英文别名: 7,9,20,22-Tetrakis(bromomethyl)-4,12,17,25-tetrakis-(4-methylphenyl)sulfonyl-4,12,17,25-tetrazapentacyclo[13.11.1.12,14.16,10.119,23]triaconta-1(27),2(29),6(30),7,9,14,19,21,23(28)-nonaene
• CAS: 156417-91-3
• 化学式: C₅₈H₅₈Br₄N₄O₈S₄
• 分子量: 1387.0
• InChiKey: RYLTUCPJSAVTFS-UHFFFAOYSA-N

物化性质

• 密度：
  1.574±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  78
• 可旋转键数：
  12
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  183
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  5,7,23,25-Tetrakis(brommethyl)-2,11,20,29-tetrakis(p-tolylsulfonyl)-2,11,20,29-tetraaza[3.3](1,3)(1,3)[3.3](4,6)(1,3)benzeno[3]phan 在 三溴化磷 作用下， 以 氯仿 为溶剂， 反应 96.0h， 以35%的产率得到6,48-Bis(bromomethyl)-2,11,20,29,32,41,44,53-octakis(4-tolylsulfonyl)-2,11,20,29,32,41,44,53-octaaza[3.3](1,3)(1,3)[3.3](4,6)(1,3)[3.3](4,6)(1,3)[3.3](4,6)(1,3)benzeno[5]phane
  参考文献：
  名称：

  Linear and Macrocyclic Molecular Thread, Ribbon and Belt Assemblies of Nanometric Scale

  摘要：

  通过重复合成法，制备出了基于苯连接的 [3.3]metacyclophane 单元的迄今为止最长的分子线带组合物 8、29、32 和 43。通过包括环化环烷骨架和酯基衍生化在内的迭代序列，成功制备了双官能化[3.3]偏环烷单元（14、22、26），并获得了良好的收率。与仅环烷带相比，[3.3]偏环烷带部分与螺纹部分的共价连接可提高产品收率。最终的分子间大环化是通过二酰胺、二硫醇或二溴化物官能化带片段的反应来完成的，以便在大环螺纹带组件（"假环"）中获得最少的单桥苯单元。

  DOI：

  10.1055/s-1999-3385
• 作为产物：
  描述：

  四溴甲苯 在 锂硼氢 、 氢溴酸 、 potassium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 5,7,23,25-Tetrakis(brommethyl)-2,11,20,29-tetrakis(p-tolylsulfonyl)-2,11,20,29-tetraaza[3.3](1,3)(1,3)[3.3](4,6)(1,3)benzeno[3]phan
  参考文献：
  名称：

  Josten, Wolfgang; Karbach, Detlef; Nieger, Martin, Chemische Berichte, 1994, vol. 127, # 4, p. 767 - 778

  摘要：

  DOI：

文献信息

• An iterative synthetic approach to nanometre-scale molecular ribbons
  作者：Stefan Breidenbach、Stefan Ohren、Martin Nieger、Fritz Vögtle

  DOI：10.1039/c39950001237

  日期：——

  The hitherto longest molecular ribbons (4–6), composed of several [3.3]metacyclophane units, are synthesized using a new iterative synthetic strategy, up to a length of seven fourfold-bridged benzene rings, and it is proved by X-ray crystal structural analyses and 1H NMR spectroscopy that these molecules form meander-type folded syn conformations leading to multiple π-staples.

  通过 X 射线晶体结构分析和 1H NMR 光谱分析证明，这些分子形成了蜿蜒型折叠合成构象，导致多个 π-带。
• Broad Molecular Ribbons of Nanometer Size Composed of Biphenyl Units
  作者：Wolfgang Boomgaarden、Fritz Vögtle、Martin Nieger、Heike Hupfer

  DOI：10.1002/(sici)1521-3765(19990104)5:1<345::aid-chem345>3.0.co;2-t

  日期：1999.1.4

  The new tetrafunctionalized biphenyl key building blocks 16 and 39 led, for the first time, to the hitherto broadest molecular ribbons that contain biphenyl units in a transverse arrangement by iterative synthetic methods. The length and breadth of the molecular ribbons, as single chemical entities, are diversified. They can be used as cyclization precursors in the synthesis of long molecular tubes of type 2 with a large diameter. The solubility and the host-guest behavior (clathrate formation with benzene, dimethylformamide, and dichloromethane) of these nanometer-size molecular ribbons were optimized by the introduction of various side chains (benzenesulfonamide, 4-toluenesulfonamide, and 4-terf-butylbenzenesulfonamide groups) into the skeleton of the ribbons. New 14-, 15-, and 16-membered model ring systems (compounds 20a, 22a, and 24 respectively) were synthesized in order to examine the constitution of the 16-membered diaza[3.3]-phane 18a. Nanometer-size tube-shaped molecules 7a, 7b and 8 were obtained by cyclization of tetrafunctionalized molecular ribbons with the biphenyl building block. The constitution and conformation of the molecular ribbons and belts were proven by NOE experiments and X-ray analyses.
• Josten, Wolfgang; Neumann, Susanne; Voegtle, Fritz, Chemische Berichte, 1994, vol. 127, # 10, p. 2089 - 2096
  作者：Josten, Wolfgang、Neumann, Susanne、Voegtle, Fritz、Nieger, Martin、Haegele, Klaus、et al.

  DOI：——

  日期：——
• Breidenbach, Stefan; Ohren, Stefan; Voegtle, Fritz, Chemistry - A European Journal, 1996, vol. 2, # 7, p. 832 - 837
  作者：Breidenbach, Stefan、Ohren, Stefan、Voegtle, Fritz

  DOI：——

  日期：——
• Linear and Macrocyclic Molecular Thread, Ribbon and Belt Assemblies of Nanometric Scale
  作者：Holger Schwierz、Fritz Vögtle

  DOI：10.1055/s-1999-3385

  日期：1999.2

  The hitherto longest molecular thread-belt assemblies 8, 29, 32 and 43 based on benzene-connected [3.3]metacyclophane units were prepared by means of a repetitive synthetic method. The preparation of difunctionalized [3.3]metacyclophane units (14, 22, 26) succeeded in good yields by an iteration sequence including the cyclization to the cyclophane skeleton and the derivatization of the ester groups. The covalent linkage of the [3.3]metacyclophane belt parts to the thread part leads to higher product yields compared to cyclophane belts only. The final intermolecular macrocyclizations are done by reaction of diamide, dithiol or dibromide functionalized belt fragments to obtain a minimum of single bridged benzene units in the macrocyclic thread-belt assemblies ("pseudobelts").

  通过重复合成法，制备出了基于苯连接的 [3.3]metacyclophane 单元的迄今为止最长的分子线带组合物 8、29、32 和 43。通过包括环化环烷骨架和酯基衍生化在内的迭代序列，成功制备了双官能化[3.3]偏环烷单元（14、22、26），并获得了良好的收率。与仅环烷带相比，[3.3]偏环烷带部分与螺纹部分的共价连接可提高产品收率。最终的分子间大环化是通过二酰胺、二硫醇或二溴化物官能化带片段的反应来完成的，以便在大环螺纹带组件（"假环"）中获得最少的单桥苯单元。