(+/-)-2,7,12-Tris(aminoethylcarbamoylmethoxy)-3,8,13-trimethoxy-10,15-dihydro-5H-tribenzocyclononene | 161955-59-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (+/-)-2,7,12-Tris(aminoethylcarbamoylmethoxy)-3,8,13-trimethoxy-10,15-dihydro-5H-tribenzocyclononene
• 英文别名: (+/-)-2,7,12-tris(2-aminoethyl carbamoylmethoxy)-3,18,13-trimethoxy-10,15-dihydro-5H-tribenzo[a,d,g]cyclononene；(+/-)-2,7,12-tris(2-aminoethylcarbamoylmethoxy)-3,8,13-trimethoxy-10,15-dihydro-5H-tribenzo[a,d,g]cyclononene
• CAS: 161955-59-5
• 化学式: C₃₆H₄₈N₆O₉
• 分子量: 708.812
• InChiKey: LXUNIJRRKOWULV-UHFFFAOYSA-N

物化性质

• 沸点：
  1011.7±65.0 °C(Predicted)
• 密度：
  1.242±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.16
• 重原子数：
  51.0
• 可旋转键数：
  18.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  220.74
• 氢给体数：
  6.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (+/-)-2,7,12-Tris(aminoethylcarbamoylmethoxy)-3,8,13-trimethoxy-10,15-dihydro-5H-tribenzocyclononene 、 Thioctic acid 在 三乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以67%的产率得到
  参考文献：
  名称：

  Selective Anion Sensing by a Tris-Amide CTV Derivative:  ¹H NMR Titration, Self-Assembled Monolayers, and Impedance Spectroscopy

  摘要：

  A hydrogen-bond forming tris(amide) receptor based on cyclotriveratrylene (CTV) was prepared. Self-assembled monolayers; (SAMS) of the receptor were formed on gold surfaces. Desorption experiments show a surface coverage of 2.26 x 10(-10) Mol/cm(2). H-1 NMR and UV measurements confirm that the receptor exhibits the highest affinity for acetate ions among the anions studied. Electrochemical impedance was used to investigate anion sensing by the SAMS and proved to be an efficient and convenient technique for detecting anions in aqueous solutions. Upon binding acetate anions, the monolayer-modified gold electrodes show a drastic increase of the R-ct values when Fe(CN)(6)(3-)/(4-) is used as the redox probe. When the probe was changed to a positively charged one, Ru(NH3)(6)(3+/2+), the R-ct values decreased monotonically as the acetate concentration was increased, thus confirming the accumulation of negative surface charge upon anion binding. H2PO4- shows some interference when sensing AcO-. Other monovalent anions such as Cl-, Br-, NO3-, and HSO4- do not bind to the CTV receptor either in solution or on the surfaces.

  DOI：

  10.1021/ja044411h
• 作为产物：
  描述：

  4-羟基-3-甲氧基苄醇 在 sodium iodide 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 125.0h， 生成 (+/-)-2,7,12-Tris(aminoethylcarbamoylmethoxy)-3,8,13-trimethoxy-10,15-dihydro-5H-tribenzocyclononene
  参考文献：
  名称：

  结合阳离子-π和阴离子-π相互作用进行两性离子识别

  摘要：

  兄弟与敌人：阴离子-π和阳离子-π相互作用聚集在半色氨酸宿主的分子腔中时起协同作用，为两性离子识别提供了有效的贡献（−170 kJ mol -1）。NMR滴定实验和计算揭示了客体在异位受体腔中的位置。这项研究强调了阴离子-π键在主体-客体化学中的重要性。

  DOI：

  10.1002/anie.201106934

文献信息

• A hemicryptophane with a triple-stranded helical structure
  作者：Augustin Long、Olivier Perraud、Erwann Jeanneau、Christophe Aronica、Jean-Pierre Dutasta、Alexandre Martinez

  DOI：10.3762/bjoc.14.162

  日期：——

  five steps. The X-ray molecular structure of the cage shows a triple-stranded helical arrangement of the linkers stabilized by intramolecular hydrogen bonds between amide and amine groups. The chirality of the cyclotriveratrylene unit controls the propeller arrangement of the three aromatic rings in the opposite part of the cage. 1H NMR studies suggest that this structure is retained in solution.

  通过五个步骤合成了在其三个接头中具有胺和酰胺功能的半色氨酸笼。笼子的X射线分子结构显示了通过酰胺和胺基团之间的分子内氢键稳定的接头的三链螺旋排列。环三碳杂戊二烯单元的手性控制在笼子相对部分的三个芳环的螺旋桨布置。1 H NMR研究表明该结构保留在溶液中。
• New organogelators based on cyclotriveratrylene platforms bearing 2-dimethylacetal-5-carbonylpyridine fragments
  作者：David Bardelang、Franck Camerel、Raymond Ziessel、Marc Schmutz、Michael J. Hannon

  DOI：10.1039/b712413a

  日期：——

  Gelators, compounds able to solidify solvents, and in particular hydrogelators are interesting soft materials. In this paper we have synthesized cyclotriveratrylene (CTV) platforms symmetrically end-substituted with pendent primary amines or nicotamic substituents. These non-amphiphilic structures induce self-assembly in a large variety of solvents forming robust and opaque gels. Cyclotriveratrylene gels have for the first time been formed and characterized using FT-IR and freeze fracture electron microscopy. Two hierarchical events are responsible for the gel structure. Individual fibres of 4–5 nm diameter are formed by aggregation of the functionalised CTV molecules. These fibres then further self-assemble into large ribbons several µm long and 20 to 40 nm wide. Within the ribbons the fine striations observed by FFEM are due to individual straight chains organized in a highly compacted state. Within the fibres the individual CTV molecules are held together by hydrogen bonding of the amide function as probed by infra-red spectroscopy.

  凝胶剂是一类能够使溶剂固化的化合物，特别是水凝胶剂，是有趣的软材料。在本文中，我们合成了对称末端取代有侧基的初级胺或尼古丁取代基的环三维紫烯（CTV）平台。这些非两亲性结构在多种溶剂中诱导自组装，形成坚固而不透明的凝胶。环三维紫烯凝胶首次使用傅里叶变换红外光谱（FT-IR）和冷冻断裂电子显微镜（FFEM）进行了表征。凝胶结构由两个层次的事件组成。直径为4–5纳米的单个纤维是通过功能化的CTV分子的聚集形成的。这些纤维进一步自组装成几微米长、20至40纳米宽的大带状结构。在带状结构内，FFEM观察到的细条纹是由于个别直链以高度压缩的状态组织在一起。在纤维内，个别的CTV分子通过酰胺功能的氢键结合在一起，这一点通过红外光谱得到了验证。
• Synthesis of C3-cyclotriveratrylene ligands for iron(II) and iron(III) coordination
  作者：Gilles Vériot、Jean-Pierre Dutasta、Galina Matouzenko、André Collet

  DOI：10.1016/0040-4020(94)00904-9

  日期：1995.1

  The design and synthesis of a new family of siderophores based on cyclotriveratrylene is described. The ligands consist of a C3-cyclotriveratrylene unit provided with three arms (spacers) ending with hydroxamate, catecholate, bipyridine, or iminopyridine units suitable for the octahedral coordination of transition metals and particularly for the complexation of iron(II) and iron(III).

  描述和设计了基于环三藜芦烯的新型铁载体家族。配体由一个C3-环三碳杂戊二烯单元和三个臂（间隔基）组成，它们的末端为异羟肟酸酯，邻苯二酚，联吡啶或亚氨基吡啶单元，适用于过渡金属的八面体配位，特别是铁（II）和铁（III）的络合。
• Complexation and electrochemical sensing of anions by amide-substituted ferrocenyl ligands
  作者：Olivier Reynes、Frederic Maillard、Jean-Claude Moutet、Guy Royal、Eric Saint-Aman、Gabriella Stanciu、Jean-Pierre Dutasta、Isabelle Gosse、Jean-Christophe Mulatier

  DOI：10.1016/s0022-328x(01)00935-4

  日期：2001.12

  depends on the number of ferrocene centers and amide groups in the receptor, and on the accessibility of the binding sites. Clear two-wave cyclic voltammetry features allowed the amperometric titration of H2PO4− and ATP2− by ligands L4 and L5 built from a cyclotriveratrylene structural unit, and containing a combination of three ferrocene centers with three (L4) or six (L5) amide groups.

  新含酰胺的二茂铁基配体，大号1 - 5，制备和伏安和1个阴离子的1 H NMR调查结合物在有机介质中进行。的电化学识别能力大号1 - 5朝˚F -，HSO 4 -，H 2 PO 4 -和ATP 2-“氢键”是基于阴离子络合到还原的中性配体的氢键与酰胺质子之间的协同作用以及配体的氧化阳离子形式形成的离子对相互作用。阴离子-配体相互作用的强度取决于受体中二茂铁中心和酰胺基团的数量，以及结合位点的可及性。澄清的两波循环伏安法的特征允许H的电流滴定2 PO 4 -和ATP 2-通过配体大号4和大号5从cyclotriveratrylene结构单元建成，和含有三种二茂铁中心具有三个（组合大号4）或六（L5）酰胺基。