bis(m-phenylene)-32-crown-10 | 64739-07-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: bis(m-phenylene)-32-crown-10
• 英文别名: bis(1,3-phenylene)-32-crown-10；BMP32C10；2,5,8,11,14,20,23,26,29,32-Decaoxatricyclo[31.3.1.1(15,19)]octatriaconta-1(37),15,17,19(38),33,35-hexaene；2,5,8,11,14,20,23,26,29,32-decaoxatricyclo[31.3.1.115,19]octatriaconta-1(37),15(38),16,18,33,35-hexaene
• CAS: 64739-07-7
• 化学式: C₂₈H₄₀O₁₀
• 分子量: 536.62
• InChiKey: PQGWMOBEFDKNRX-UHFFFAOYSA-N

物化性质

• 沸点：
  693.4±55.0 °C(Predicted)
• 密度：
  1.068±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  38
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  92.3
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  bis(m-phenylene)-32-crown-10 、 dibenzylammonium hexafluorophosphate 以 丙酮 为溶剂， 生成
  参考文献：
  名称：

  A Study of the Complexation of Bis(m-Phenylene) Crown Ethers and Secondary Ammonium Ions

  摘要：

  Two macrocycles, bis(m-phenylene)-26-crown-8 (1) and bis(m-phenylene)-32-crown-10 (2), were combined with several linear components, dibenzyl- (3 . PF6), di-n-butyl- (4 . PF6), and diphenethyl-(5 . PF6) ammonium hexafluorophosphate salts. The smaller macrocycle 1 was shown not to complex effectively with any of the ammonium salts in solution by H-1 NMR, but 1:1 complexes were shown to exist in the "gas phase" as [1:3], [1:4], and [1:5] by high-resolution fast atom bombardment mass spectrometry (HRFABMS) and electrospray ionization mass spectrometry (ESIMS). The X-ray crystal structure of macrocycle 1 is reported. The larger macrocycle 2 did form 1:2 complexes with the ammonium salts in solution, which were observed as well in the solid and gas phases. X-ray crystal structures of the pseudorotaxanes [2:(3)(2)]. 2PF(6) and [2:(5)(2)]. 2PF(6) were determined and are discussed. The pseudorotaxanes are stabilized by hydrogen bonding between the ammonium hydrogens of the linear salt unit and the oxygens of the crown ether macrocycle. Secondary stabilization also occurs by edge-to-face pi stacking.

  DOI：

  10.1021/jo972162s
• 作为产物：
  描述：

  3-苄氧基苯酚 在 palladium on activated charcoal 、 氢气 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 49.0h， 生成 bis(m-phenylene)-32-crown-10
  参考文献：
  名称：

  联苯并亚苯基-32-冠-10衍生物对百草枯和敌草快的络合作用

  摘要：

  Uv和1 H nmr光谱研究了[Paraquat] [PF 6 ] 2和[Diquat] [PF 6 ] 2形成的1：1配合物，该配合物由bismetaphenylene-32-crown-10衍生物（BMP32C10）支持，游离BMP32C10和[Diquat·BMP32C10] [PF 6 ] 2 ·Me 2 CO上的X射线晶体结构为分子间非共价相互作用的电子和空间性质提供了进一步的基本理解，这对于成功设计和合成BMP32C10至关重要。最佳结合[Paraquat] 2+药物的分子受体。

  DOI：

  10.1039/c39870001058

文献信息

• pH-responsive assembly and disassembly of a supramolecular cryptand-based pseudorotaxane driven by π–π stacking interaction
  作者：Xuzhou Yan、Mingming Zhang、Peifa Wei、Bo Zheng、Xiaodong Chi、Xiaofan Ji、Feihe Huang

  DOI：10.1039/c1cc13472h

  日期：——

  Driven by π–π stacking interaction, a supramolecular cryptand-based [2]pseudorotaxane was formed and its formation was demonstrated to be pH-responsive.

  受π-π堆积相互作用的驱动，形成了一种基于超分子密钥的[2]假旋转结构，并且其形成被证明具有pH响应性。
• Solid state structure of dibenzo-crown ethers formally derived from resorcinol. X-ray crystal structure, solid state 13 C NMR and solution NMR properties of dibenzo-32-crown-10
  作者：G.W. Buchanan、R.C. Laister、G.P.A. Yap

  DOI：10.1016/s0022-2860(99)00375-0

  日期：2000.5

  Abstract The X-ray crystal structure of the title molecule indicates that all four O–C–C–O torsional networks possess normal gauche-type geometries. This is in contrast to the dibenzo-20-crown-6 and and dibenzo-26-crown-8 analogs in which at least one transoid O–C–C–O unit is present. 13C NMR chemical shift differences are discussed in terms of the solid state geometry. In particular, there is a 7 ppm

  摘要 标题分子的 X 射线晶体结构表明所有四种 O-C-C-O 扭转网络都具有正常的 gauche 型几何结构。这与 dibenzo-20-crown-6 和 dibenzo-26-crown-8 类似物形成对比，其中至少存在一个 transoid O-C-C-O 单元。13C NMR 化学位移差异根据固态几何形状进行讨论。特别是，在氧邻位的两个芳族碳之间存在 7 ppm 的差异，而在溶液中，由于构象平均，这些位点的化学位移是相同的。
• A Bis(m-phenylene)-32-crown-10/Paraquat [2]Rotaxane
  作者：Shijun Li、Kelong Zhu、Bo Zheng、Xianhong Wen、Ning Li、Feihe Huang

  DOI：10.1002/ejoc.200801128

  日期：2009.3

  successful preparation of the first bis(m-phenylene)-32-crown-10/paraquat [2]rotaxane showed unambiguously that psuedorotaxane-type complexation, rather than the taco-complex-type complexation previously observed in the solid state and in solution, exists – in solution – for complexation between bis(m-phenylene)-32-crown-10 derivatives and paraquat derivatives.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451

  第一个双（间亚苯基）-32-冠-10/百草枯[2]轮烷的成功制备明确表明，假轮烷型络合，而不是先前在固态和溶液中观察到的塔科络合物型络合, 存在于溶液中，用于双(间亚苯基)-32-crown-10 衍生物和百草枯衍生物之间的络合。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Amabilino, David B.; Anelli, Pier-Lucio; Ashton, Peter R., Journal of the American Chemical Society, 1995, vol. 117, # 45, p. 11142 - 11170
  作者：Amabilino, David B.、Anelli, Pier-Lucio、Ashton, Peter R.、Brown, George R.、Córdova, Emilio、Godínez, Luis A.、Hayes, Wayne、Kaifer, Angel E.、Philp, Douglas、Slawin, Alexandra M. Z.、Spencer, Neil、Stoddart, J. Fraser、Tolley, Malcolm S.、Williams, David J.

  DOI：——

  日期：——
• Bis(m-phenylene)-32-crown-10/monopyridinium [2]pseudorotaxanes
  作者：Feihe Huang、Carla Slebodnick、Amy E. Ratliff、Harry W. Gibson

  DOI：10.1016/j.tetlet.2005.07.011

  日期：2005.9

  The first crown ether/monopyridinium threaded structures, which are [2]pseudorotaxanes based on a new bis(m-phenylene)-32-crown-10/monopyridinium recognition motif, were successfully prepared as confirmed by proton NMR spectroscopy, electrospray ionization mass spectrometry, and X-ray analysis. (c) 2005 Elsevier Ltd. All rights reserved.