1(1,5)-naphthalena 15(1,3)-(5-carboxybenzena)-2,5,8,11,14,16,19,22,25,28-decaoxacyclo-octacosaphane | 200809-08-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1(1,5)-naphthalena 15(1,3)-(5-carboxybenzena)-2,5,8,11,14,16,19,22,25,28-decaoxacyclo-octacosaphane
• 英文别名: 2,5,8,11,14,25,28,31,34,37-Decaoxatetracyclo[36.3.1.015,20.019,24]dotetraconta-1(42),15,17,19,21,23,38,40-octaene-40-carboxylic acid
• CAS: 200809-08-1
• 化学式: C₃₃H₄₂O₁₂
• 分子量: 630.689
• InChiKey: WHJRLBBKAJGSOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  45
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1(1,5)-naphthalena 15(1,3)-(5-carboxybenzena)-2,5,8,11,14,16,19,22,25,28-decaoxacyclo-octacosaphane 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-[2-[2-[4,7-Bis(bromomethyl)-1,3-dioxoisoindol-2-yl]acetyl]oxyethoxy]ethyl 2,5,8,11,14,25,28,31,34,37-decaoxatetracyclo[36.3.1.015,20.019,24]dotetraconta-1(42),15,17,19,21,23,38,40-octaene-40-carboxylate
  参考文献：
  名称：

  Dynamic Chirality in Donor−Acceptor Pretzelanes

  摘要：

  A series of donor-acceptor pretzelanes has been synthesized, using self-assembly and template-directed protocols, and the dynamic processes that these pretzelanes undergo have been investigated in solution. These compounds exist as libraries of diastereoisomers as a result of their multiple stereoelements, which are dynamically interconverted by several different, in some cases competing, processes. Altering the structure of the pretzelanes changes the rates and mechanisms by which these diastereoisomers equilibrate. Additionally, inserting an element of fixed chirality allows the equilibrium to be biased, while maintaining the barrier to the equilibration processes. These results bode well for the future construction of molecular devices based on switchable diastereoisomerism involving metastable states.

  DOI：

  10.1021/jo051430g
• 作为产物：
  描述：

  3,5-二羟基苯甲酸甲酯 在 sodium hydroxide 、 potassium carbonate 作用下， 以 丙酮 、 甘油 为溶剂， 生成 1(1,5)-naphthalena 15(1,3)-(5-carboxybenzena)-2,5,8,11,14,16,19,22,25,28-decaoxacyclo-octacosaphane
  参考文献：
  名称：

  Flexible self-assembling porphyrin supramolecules

  摘要：

  讨论了利用冠状醚-萘二酰亚胺主客体化学和金属卟啉-吡啶配位的一系列混合柔性自组装超分子化合物的设计和化学合成。通过多种技术，包括扩散排序核磁共振波谱学（DOSY）和冷喷雾离子化质谱法（CSI-MS），探究所得化合物的结构和动态特性。

  DOI：

  10.1039/b506987d

文献信息

• Donor-Acceptor Pretzelanes and a Cyclic Bis[2]catenane Homologue
  作者：Yi Liu、Paul A. Bonvallet、Scott A. Vignon、Saeed I. Khan、J. Fraser Stoddart

  DOI：10.1002/anie.200500041

  日期：2005.5.13
• Sn(IV) Porphyrins as NMR Shift Reagents and Supramolecular Protecting Groups:  Preparation of a Carboxylate−Catenane Porphyrin Complex
  作者：Yin Tong、Darren G. Hamilton、Jean-Christophe Meillon、Jeremy K. M. Sanders

  DOI：10.1021/ol990891j

  日期：1999.11.1

  Coordination of a carboxylic acid diaryl crown ether to a Sn(IV) porphyrin promotes its ability to act as a template for the formation of a [2]catenane: in the absence of the porphyrin the acid-crown yields only a tiny amount of the interlocked derivative, Once isolated the free acid-[2]catenane presents extremely broad resonances in its 500 MHz H-1 NMR spectrum, but complexation to a Sn(IV) porphyrin results in dramatic resolution via a combination of dynamic and dispersive effects.
• Dynamic Chirality in Donor−Acceptor Pretzelanes
  作者：Y. Liu、S. A. Vignon、X. Zhang、P. A. Bonvallet、S. I. Khan、K. N. Houk、J. F. Stoddart

  DOI：10.1021/jo051430g

  日期：2005.11.1

  A series of donor-acceptor pretzelanes has been synthesized, using self-assembly and template-directed protocols, and the dynamic processes that these pretzelanes undergo have been investigated in solution. These compounds exist as libraries of diastereoisomers as a result of their multiple stereoelements, which are dynamically interconverted by several different, in some cases competing, processes. Altering the structure of the pretzelanes changes the rates and mechanisms by which these diastereoisomers equilibrate. Additionally, inserting an element of fixed chirality allows the equilibrium to be biased, while maintaining the barrier to the equilibration processes. These results bode well for the future construction of molecular devices based on switchable diastereoisomerism involving metastable states.
• Flexible self-assembling porphyrin supramolecules
  作者：Ken D. Johnstone、Kentaro Yamaguchi、Maxwell J. Gunter

  DOI：10.1039/b506987d

  日期：——

  The design and chemical synthesis of a series of hybrid flexible self-assembling supramolecules utilising both crown ether–naphthalene diimide host–guest chemistry and metalloporphyrin–pyridyl coordination is discussed. The resulting compound structures and dynamics are probed using a variety of techniques, including diffusion ordered NMR spectroscopy (DOSY) and cold-spray ionisation mass spectrometry (CSI-MS).

  讨论了利用冠状醚-萘二酰亚胺主客体化学和金属卟啉-吡啶配位的一系列混合柔性自组装超分子化合物的设计和化学合成。通过多种技术，包括扩散排序核磁共振波谱学（DOSY）和冷喷雾离子化质谱法（CSI-MS），探究所得化合物的结构和动态特性。