5,11,17,23-tetra-tert-butyl-25,27-bis[(benzimidazol-2-ylmethyl)carbamoylmethoxy]-26,28-dihydroxycalix[4]arene | 1058105-78-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 5,11,17,23-tetra-tert-butyl-25,27-bis[(benzimidazol-2-ylmethyl)carbamoylmethoxy]-26,28-dihydroxycalix[4]arene
• 英文别名: N-(1H-benzimidazol-2-ylmethyl)-2-[[27-[2-(1H-benzimidazol-2-ylmethylamino)-2-oxoethoxy]-5,11,17,23-tetratert-butyl-26,28-dihydroxy-25-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaenyl]oxy]acetamide
• CAS: 1058105-78-4
• 化学式: C₆₄H₇₄N₆O₆
• 分子量: 1023.33
• InChiKey: UOOQFISZLFKYIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.5
• 重原子数：
  76
• 可旋转键数：
  14
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  175
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (1H-苯并咪唑-2-亚甲基)胺 、 5,11,17,23-tert-butyl-25,27-bis(chlorocarbonylmethoxy)-26,28-hydroxycalix[4]arene 在 盐酸 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以55%的产率得到5,11,17,23-tetra-tert-butyl-25,27-bis[(benzimidazol-2-ylmethyl)carbamoylmethoxy]-26,28-dihydroxycalix[4]arene
  参考文献：
  名称：

  Ratiometric fluorescence off-on-off sensor for Cu2+ in aqueous buffer by a lower rim triazole linked benzimidazole conjugate of calix[4]arene

  摘要：

  一种苯并咪唑附加三唑连接的 1,3-二共轭钙[4]炔（L）已被合成并表征。在所研究的 13 种不同金属离子中，共轭物 L 通过在 ∼380 nm 处新产生的准分子带显示出比率荧光变化，从而识别 Cu2+。通过荧光、ESI MS 和 1H NMR 滴定中观察到的变化，可以诱发这种结合。所研究的所有其他金属离子都没有显示任何新的波段，也不会进一步干扰 L 对 Cu2+ 的识别，即使这些金属离子存在于同一介质中也是如此。通过 DFT 计算确定了单核和双核配合物的结构特征，并发现铜中心的几何形状高度扭曲，偏离了四面体和方形平面。

  DOI：

  10.1039/c2dt30432e

文献信息

• Experimental and Computational Studies of Selective Recognition of Hg²⁺ by Amide Linked Lower Rim 1,3-Dibenzimidazole Derivative of Calix[4]arene: Species Characterization in Solution and that in the Isolated Complex, Including the Delineation of the Nanostructures
  作者：Roymon Joseph、Balaji Ramanujam、Amitabha Acharya、Anupam Khutia、Chebrolu P. Rao

  DOI：10.1021/jo800073g

  日期：2008.8.1

  Amide linked lower rim 1,3-dibenzimidazole derivative of calix[4]arene, L has been shown to be sensitive and selective to Hg2+ in aqueous acetonitrile solution based on fluorescence spectroscopy, and the stoichiometry of the complexed species has been found to be 1:1. The selectivity of L toward Hg2+ has been shown among 11 M2+ ions, viz., Mn2+, Fe2+, CO2+, Ni2+, Cu2+, Zn2+, Cd2+, Hg2+, Ph2+, Ca2+, and Mg2+ studied, including those of the mercury group and none of these ions impede the recognition of Hg2+ by L. Role of the solvent on the recognition of Hg2+ has been demonstrated. The role of calix[4]arene platform and the benzimidazole moieties in the recognition of Hg2+ by L has been delineated upon performing such studies with five different molecules of relevance as reference molecular systems. The binding cores formed by the receptor L and the reference compounds have been established based on the single crystal XRD structures, and the preferential metal ion binding cores have been discussed. The binding, of Hg2+ with L has been further established based on H-1 and C-13 NMR, ESI MS, absorption, and fluorescence lifetime measurements. Some of these techniques have been used to establish the stoichiometry of the species formed. The complex species formed between L and Hg2+ have been isolated and characterized and found to be 1:1 species even in the isolated complex. Whereas transmission electron microscopy (TEM), atomic force microscopy (AFM), and scanning electron microscopy (SEM) provided the nanostructural behavior of L, the TEM and SEM demonstrated that the mercury complex has different characteristics when compared to L. The TEM, SEM, and powder XRD studies revealed that whereas L is crystalline, that of the mercury complex is not, perhaps a reason for not being able to obtain single crystals of the complex. Binding characteristics of Hg2+ toward L have been established based on the DFT computational calculations.
• Synthesis of derivatives of p-tert-butylcalix[4]arene containing on lower rim fragments of 2-aminoalkylbenzimidazoles
  作者：E. A. Alekseeva、A. P. Luk’yanenko、S. S. Basok、A. V. Mazepa、A. I. Gren’

  DOI：10.1134/s107042801009023x

  日期：2010.9

  Reactions of calix[4]arene carboxymethoxy derivatives with 2-aminoalkylbenzimidazoles in the presence of dicyclohexylcarbodiimide and hydroxybenzotriazole afforded a series of p-tert-butylcalix[4]arene derivatives containing on the lower rim N-(2-benzimidazolylalkyl)carbamoylmethoxy fragments. The reaction carried out in the absence of hydroxybenzOtriazole resulted in macrocycles containing one N-(2-benzimidazolylalkyl)carbamoyl fragment and a fragment of N-(acyl)dicyclohexylisourea.
• Ratiometric fluorescence off-on-off sensor for Cu2+ in aqueous buffer by a lower rim triazole linked benzimidazole conjugate of calix[4]arene
  作者：Rakesh Kumar Pathak、Vijaya Kumar Hinge、Prasenjit Mondal、Chebrolu Pulla Rao

  DOI：10.1039/c2dt30432e

  日期：——

  A benzimidazole appended triazole linked 1,3-diconjugate of calix[4]arene (L) has been synthesized and characterized. The conjugate L has been found to recognize Cu2+ among the thirteen different metal ions studied by exhibiting ratiometric fluorescence changes through newly generated excimer band at ∼380 nm. Fluorescence off–on–off behavior has been clearly demonstrated on the basis of the binding variability of Cu2+ to L. The binding has been elicited through the changes observed in the fluorescence, ESI MS and 1H NMR titrations. All the other metal ions studied do not show any new band and further do not interfere with the recognition of Cu2+ by L, even when these are present in the same medium. The structural features of both the mono- and di-nuclear complexes were established by DFT computational calculations and found to display highly distorted geometry about the copper centers that deviate from both the tetrahedral and the square planar.

  一种苯并咪唑附加三唑连接的 1,3-二共轭钙[4]炔（L）已被合成并表征。在所研究的 13 种不同金属离子中，共轭物 L 通过在 ∼380 nm 处新产生的准分子带显示出比率荧光变化，从而识别 Cu2+。通过荧光、ESI MS 和 1H NMR 滴定中观察到的变化，可以诱发这种结合。所研究的所有其他金属离子都没有显示任何新的波段，也不会进一步干扰 L 对 Cu2+ 的识别，即使这些金属离子存在于同一介质中也是如此。通过 DFT 计算确定了单核和双核配合物的结构特征，并发现铜中心的几何形状高度扭曲，偏离了四面体和方形平面。