1,2,4,5-tetrakis<(4-tolylsulfonylamino)methyl>benzene | 156417-88-8

• 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: 1,2,4,5-tetrakis<(4-tolylsulfonylamino)methyl>benzene
• 英文别名: 1,2,4,5-Tetrakis[(4-tolylsulfonyl)aminomethyl]benzene；1,2,4,5-Tetrakis[(p-tolylsulfonylamino)methyl]benzol；4-methyl-N-[[2,4,5-tris[[(4-methylphenyl)sulfonylamino]methyl]phenyl]methyl]benzenesulfonamide
• CAS: 156417-88-8
• 化学式: C₃₈H₄₂N₄O₈S₄
• 分子量: 811.037
• InChiKey: VCDSAAMZVHGCNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  54
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  218
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1,2,4,5-tetrakis<(4-tolylsulfonylamino)methyl>benzene 在 锂硼氢 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 5,7,23,25-tetrakis(hydroxymethyl)-2,11,20,29-tetrakis(4-tolylsulfonyl)-2,11,20,29-tetraaza<3.3>(1,3)(1,3)<3.3>(4,6)(1,3)benzeno<3>phane
  参考文献：
  名称：

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

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2,4,5-Tetrakis<methyl>benzol 在 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以82%的产率得到1,2,4,5-tetrakis<(4-tolylsulfonylamino)methyl>benzene
  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

• 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。
• Molecular Ribbons Containing Pyridine Rings
  作者：Stefan Breidenbach、Stefan Ohren、Regine Herbst-Irmer、Sirpa Kotila、Martin Nieger、Fritz Vögtle

  DOI：10.1002/jlac.199619961225

  日期：1996.12

  folded conformation, with the pyridine and benzene units being folded in a face-to-face manner, and the tosyl units of 8–10 pointing outwards. The “intramolecular self-assembly” (folding) of these molecular ribbons is primarily attributable to the energetically more favourable syn conformation of both the [3.3]metacyclophanes and the pyridinophanes.

  描述了带状化合物6-10的首次合成。制备并表征了新的结构单元2,6-双（溴甲基）吡啶-3,5-二羧酸二乙酯1。单晶X射线结构分析表明，这些带状分子呈折叠构型排列，吡啶和苯单元面对面折叠，甲苯磺酰基单元8-10朝外。这些分子带的“分子内自组装”（折叠）主要归因于[3.3]元环phanes和吡啶并吡啶的能量上更有利的顺式构象。
• 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.
• From four-fold functionalised [3.3]cyclophanes to belt-shaped and multibridged molecules
  作者：Stefan Breidenbach、Jörg Harren、Susanne Neumann、Martin Nieger、Kari Rissanen、Fritz Vögtle

  DOI：10.1039/p19960002061

  日期：——

  Reaction of the four-fold functionalised cyclophane 7 with tetrafunctionalised aromatic building blocks such as 9 and 10 afforded the new belt-shaped molecules 3 and 4, respectively, The new four-fold bridged cyclophane 8 was synthesised by cyclisation of 7 with tosylamide monosodium salt, The macropolycycle 5, the structure of which has been confirmed by single crystal X-ray analysis, was obtained by cyclisation of the first tetrafunctionalised biphenylophane 15 with the tetrathiol 16, The constitution and conformation of compounds 3, 5 and 8 were examined by VT-NMR studies and HH-NOE experiments, Crystallisation of 8 from two different solvents leads to guest-dependent conformational changes revealed by X-ray analysis, The results described demonstrate that molecular belts and tubes of different type and size are accessible by varying the building blocks within our synthetic strategy.
• Supramolecular Assemblies: A Bis(pretzelane) and a Tetrakis(rotaxane)
  作者：André Mohry

  DOI：10.1055/s-1999-3591

  日期：1999.10