3'-(3,4,5-tridodecyloxy)benzoylamino-2,2’-bipyridine-3-amine | 188685-28-1

• 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: 3'-(3,4,5-tridodecyloxy)benzoylamino-2,2’-bipyridine-3-amine
• 英文别名: 3'-(3,4,5-tridodecyloxybenzoylamino)-2,2'-bipyridine-3-amine；N-[2-(3-aminopyridin-2-yl)pyridin-3-yl]-3,4,5-tridodecoxybenzamide
• CAS: 188685-28-1
• 化学式: C₅₃H₈₆N₄O₄
• 分子量: 843.29
• InChiKey: CHGJMBXKZWPCDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.88
• 重原子数：
  61.0
• 可旋转键数：
  39.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  108.59
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1,3,5-苯三甲酰氯 、 3'-(3,4,5-tridodecyloxy)benzoylamino-2,2’-bipyridine-3-amine 在 TEA 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以56%的产率得到N,N',N"-Tris({3[3'-(3,4,5-tridodecyloxybenzoylamino)-2,2'-bipyridyl]})benzene-1,3,5-tricarbonamide
  参考文献：
  名称：

  基于N-酰化的2,2'-联吡啶-3,3'-二胺部分中分子内H键合的扩展核盘状液晶。

  摘要：

  一种新型的盘状分子（1 ac）已经合成并表征。通过将三个亲脂性的N-单酰化的2,2'-联吡啶-3,3'-二胺楔连接到一个中心1,3,5-苯三羰基单元来构建分子。它们显示出液晶行为，如DSC，偏振显微镜和X射线衍射所示。在所有情况下，中间相均被表征为Dho相。从（1）H NMR结果表明，由于强分子内H键，化合物1ac的内部优先采用C3对称构象，从而形成扩展的核。这个大核诱导了分子之间的强相互作用，从而导致中间相增强了热稳定性。

  DOI：

  10.1002/chem.19970030220
• 作为产物：
  描述：

  3,3'-二胺基-2,2'-联吡啶 、 3,4,5-tris(dodecanyloxy)benzoyl chloride 在 TEA 作用下， 以 乙醚 为溶剂， 反应 4.0h， 以58%的产率得到3'-(3,4,5-tridodecyloxy)benzoylamino-2,2’-bipyridine-3-amine
  参考文献：
  名称：

  基于N-酰化的2,2'-联吡啶-3,3'-二胺部分中分子内H键合的扩展核盘状液晶。

  摘要：

  一种新型的盘状分子（1 ac）已经合成并表征。通过将三个亲脂性的N-单酰化的2,2'-联吡啶-3,3'-二胺楔连接到一个中心1,3,5-苯三羰基单元来构建分子。它们显示出液晶行为，如DSC，偏振显微镜和X射线衍射所示。在所有情况下，中间相均被表征为Dho相。从（1）H NMR结果表明，由于强分子内H键，化合物1ac的内部优先采用C3对称构象，从而形成扩展的核。这个大核诱导了分子之间的强相互作用，从而导致中间相增强了热稳定性。

  DOI：

  10.1002/chem.19970030220

文献信息

• Desymmetrization of 3,3′-Bis(acylamino)-2,2′-bipyridine-Based Discotics: The High Fidelity of Their Self-Assembly Behavior in the Liquid-Crystalline State and in Solution
  作者：Michel H. C. J. van Houtem、Rafael Martín-Rapún、Jef A. J. M. Vekemans、E. W. Meijer

  DOI：10.1002/chem.200902416

  日期：2010.2.15

  studied with 1H NMR spectroscopy, whereas the self‐assembled state in apolar solution was examined with optical spectroscopy. Remarkably, these desymmetrized discotics, which lack one aliphatic wedge, behave similar to the symmetric parent compound. To prove that the stacking behavior of discotics 1 and 2 is similar to that of reported C3‐symmetrical derivatives, a mixing experiment of chiral 1 with C3‐symmetrical

  通过统计方法合成了基于3,3'-双（酰基氨基）-2,2'-联吡啶单元的两个新颖的非对称盘状分子1和2。Discotic 1具有6个手性二氢香茅醚尾巴和1个外围苯基，而Discotic 2具有6个线性十二烷基氧基尾巴和1个吡啶基外围。通过强分子内氢键的预组织和随后的芳族相互作用诱导了盘状核素的自组装。1和2的液晶度是通过偏振光学显微镜，差示扫描量热法和X射线衍射确定的。两个柱状矩形中间相（Col r），但对于C 3对称衍生物，只发现了一个Col r中间相。1在溶液中，通过1 H NMR光谱研究了氯仿中的分子溶解状态，而在非极性溶液中的自组装状态通过光谱学进行了研究。值得注意的是，这些缺乏对称性的圆盘型碟片缺少一个脂族楔形物，其行为与对称的母体化合物相似。为了证明圆盘粒子1和2的堆积行为与已报道的C 3对称衍生物的堆积行为相似，是手性1与C 3的混合实验对称的13已被采用；它表明它们确实属于一种自组装类型。UV
• Triple Helix Formation in Amphiphilic Discotics: Demystifying Solvent Effects in Supramolecular Self-Assembly
  作者：Martijn A. J. Gillissen、Marcel M. E. Koenigs、Jolanda J. H. Spiering、Jef A. J. M. Vekemans、Anja R. A. Palmans、Ilja K. Voets、E. W. Meijer

  DOI：10.1021/ja4104183

  日期：2014.1.8

  were performed on the discotic amphiphiles in mixtures of water and alcohol at temperatures between 0 °C an 90 °C. The combined results show that these amphiphilic discotic molecules self-assemble into supramolecular fibers consisting of either one or three discotic molecules in the fiber cross-section and that the presence of water induces the bundling of the supramolecular fibers. The rich phase

  制备了一组基于 3,3'-双(酰基氨基)-2,2'-联吡啶取代的苯-1,3,5-三甲酰胺基序 (BiPy-BTA) 的手性、两亲性、自组装盘状分子. 通过在分子外围的烷基和低聚（环氧乙烷）基团的不对称分布，将两亲性引入盘状分子中。小角度 X 射线散射、低温透射电子显微镜和圆二色光谱测量是在 0 °C 到 90 °C 之间的温度下对水和酒精混合物中的圆盘两亲物进行的。综合结果表明，这些两亲性盘状分子自组装成由纤维横截面中的一个或三个盘状分子组成的超分子纤维，并且水的存在诱导了超分子纤维的成束。对这些分子观察到的富相行为证明与水-醇混合物的混合热力学密切相关。
• <i>C</i>₃-Symmetrical Supramolecular Architectures:  Fibers and Organic Gels from Discotic Trisamides and Trisureas
  作者：Judith J. van Gorp、Jef A. J. M. Vekemans、E. W. Meijer

  DOI：10.1021/ja020984n

  日期：2002.12.1

  Hydrogen bonded C-symmetrical molecules that associate into supramolecular stacks are described. Structural mutation on these molecules has been performed to elucidate the contribution of the different secondary interactions (hydrogen bonding, pi-pi stacking) to the self-assembly of the disks into chiral stacks. Twelve C3-symmetrical molecules have been investigated, six of which contain three central amide functionalities (1a-f) and six of which contain three central urea groups (2a-f). Peripheral groups of the disks are "small", "medium", or "large", half of them being achiral and the other half being chiral, to enable investigation of the supramolecular architectures with CD spectroscopy. In all of the cases, elongated, helical stacks are formed in apolar solution, except for the "medium" amide disks 1c/d. The elongated stacks of the C-symmetrical disks form gels, which are visualized by AFM and SANS, and this confirms the directionality of the interactions. For the "large" urea disk, 2f, fibers with a length of up to 2 mum are observed. Temperature dependent and "sergeants-and-soldiers" CD measurements reveal that the urea stacks are much more rigid than the corresponding amide ones. In case of the "medium" urea disks, 2c/d, a true rigid rod, is formed. Where amide disks immediately reach their thermodynamic equilibrium, kinetic factors seem to govern urea aggregation. In a number of experiments aimed at reversibility with the urea stacks, hysteresis is observed, implying that these urea disks initially form a poorly defined stack, which subsequently transforms slowly into a well-defined, chiral architecture.