6,9,12,23,26,29-Hexaoxa-43,46-diazaoctacyclo[32.8.4.22,5.230,33.013,18.017,22.037,45.040,44]pentaconta-1(43),2(50),3,5(49),13,15,17,19,21,30(48),31,33(47),34(46),35,37(45),38,40(44),41-octadecaene | 176440-74-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: 6,9,12,23,26,29-Hexaoxa-43,46-diazaoctacyclo[32.8.4.22,5.230,33.013,18.017,22.037,45.040,44]pentaconta-1(43),2(50),3,5(49),13,15,17,19,21,30(48),31,33(47),34(46),35,37(45),38,40(44),41-octadecaene
• 英文别名: 6,9,12,23,26,29-hexaoxa-43,46-diazaoctacyclo[32.8.4.22,5.230,33.013,18.017,22.037,45.040,44]pentaconta-1(43),2(50),3,5(49),13,15,17,19,21,30(48),31,33(47),34(46),35,37(45),38,40(44),41-octadecaene
• CAS: 176440-74-7
• 化学式: C₄₂H₃₆N₂O₆
• 分子量: 664.758
• InChiKey: CSEOZHINALFJGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  50
• 可旋转键数：
  0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  81.2
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tetrakis(actonitrile)copper(I) hexafluorophosphate 、 、 6,9,12,23,26,29-Hexaoxa-43,46-diazaoctacyclo[32.8.4.22,5.230,33.013,18.017,22.037,45.040,44]pentaconta-1(43),2(50),3,5(49),13,15,17,19,21,30(48),31,33(47),34(46),35,37(45),38,40(44),41-octadecaene 以 二氯甲烷 、 乙腈 为溶剂， 以100%的产率得到
  参考文献：
  名称：

  A Switchable Hybrid [2]-Catenane Based on Transition Metal Complexation and π-Electron Donor−Acceptor Interactions

  摘要：

  A bimodal [2]-catenane has been synthesized via a copper(I) templated synthesis. The compound contains both a transition metal coordination site and a set of pi-electron rich and pi-electron deficient aromatic units suitable for the formation of acceptor-donor complexes. Each constituent ring is thus different from the other, and the organic backbone can adopt two favored contrasting orientations by circumrotation of one ring within the other: (i) in the metal complex mode, each dpp unit (dpp = 2,9-diphenyl-1,10-phenanthroline) is entwined about the other, while a cationic species is complexed in the coordination site thus created; (ii) in the organic pi-electron acceptor-donor complex mode, the dpp fragments are remote from one another, and the pi-electron rich and pi-electron deficient units stack to form a complex. The conversion of one binding mode to the other implies complete topographical rearrangement of the molecule. It can be triggered by adding or removing the cation center (Cu+, Li+, or H+), bonded to the dpp-containing complexing site. Interestingly, this switching process can be easily monitored by H-1 NMR, since it involves drastic relative orientational changes. It can also be evidenced by electronic spectroscopy. In particular, the proton-driven rearrangement reactions lead to significant changes in the absorption spectrum, which correspond to the appearance (by deprotonation) and disappearance (by protonation of the dpp) of a charge transfer band (around 470 nm) resulting from the pi-electron donor-acceptor noncovalent interaction.

  DOI：

  10.1021/ja954329+
• 作为产物：
  描述：

  1,5-二羟基萘 、 2,9-bis{4-{2-[2-iodoethoxy(ethoxy)]}phenyl}-1,10-phenanthroline 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以37%的产率得到6,9,12,23,26,29-Hexaoxa-43,46-diazaoctacyclo[32.8.4.22,5.230,33.013,18.017,22.037,45.040,44]pentaconta-1(43),2(50),3,5(49),13,15,17,19,21,30(48),31,33(47),34(46),35,37(45),38,40(44),41-octadecaene
  参考文献：
  名称：

  [2]环戊烷和[2]轮烷作为拓扑结构和欧几里得分子“橡胶手套”的原型。

  摘要：

  [2] catenane和[2] rotaxane已通过C2对称的2,9-二苯基-1,10-菲咯啉基（dpp基）大环化合物通过1,5-二氧萘亚基的结合而制得。过渡金属模板化技术。在链烷烃的情况下，该大环与基于dpp的大环互锁，该环通过对甲苯基取代基在菲咯啉亚基的4位上定位。在轮烷的情况下，C2对称大环被连接到一个定向的哑铃状分子上，该分子基于相同的4-对甲苯基-1,10-菲咯啉亚基，该亚基带有四芳基甲烷塞。这两个物种都是化学非手性分子，但它们完全由不对称的镜像构象组成。因此，构象对映异构化过程仅通过手性途径进行，这些分子具有“橡胶手套”的特性。但是，尽管[2]轮烷的分子图（结构式）可以变形为平面，因此可以刚性地非手性表示，但文献中一些其他化合物具有的特征是“欧几里得橡胶手套”。 ”，[2]联烷烃的分子图不能以这种方式变形。因此，它具有作为化学非手性“拓扑橡胶手套”的独特性能。

  DOI：

  10.1002/1521-3765(20011001)7:19<4085::aid-chem4085>3.0.co;2-m

文献信息

• A Switchable Hybrid [2]-Catenane Based on Transition Metal Complexation and π-Electron Donor−Acceptor Interactions
  作者：David B. Amabilino、Christiane O. Dietrich-Buchecker、Aude Livoreil、Lluïsa Pérez-García、Jean-Pierre Sauvage、J. Fraser Stoddart

  DOI：10.1021/ja954329+

  日期：1996.4.24

  A bimodal [2]-catenane has been synthesized via a copper(I) templated synthesis. The compound contains both a transition metal coordination site and a set of pi-electron rich and pi-electron deficient aromatic units suitable for the formation of acceptor-donor complexes. Each constituent ring is thus different from the other, and the organic backbone can adopt two favored contrasting orientations by circumrotation of one ring within the other: (i) in the metal complex mode, each dpp unit (dpp = 2,9-diphenyl-1,10-phenanthroline) is entwined about the other, while a cationic species is complexed in the coordination site thus created; (ii) in the organic pi-electron acceptor-donor complex mode, the dpp fragments are remote from one another, and the pi-electron rich and pi-electron deficient units stack to form a complex. The conversion of one binding mode to the other implies complete topographical rearrangement of the molecule. It can be triggered by adding or removing the cation center (Cu+, Li+, or H+), bonded to the dpp-containing complexing site. Interestingly, this switching process can be easily monitored by H-1 NMR, since it involves drastic relative orientational changes. It can also be evidenced by electronic spectroscopy. In particular, the proton-driven rearrangement reactions lead to significant changes in the absorption spectrum, which correspond to the appearance (by deprotonation) and disappearance (by protonation of the dpp) of a charge transfer band (around 470 nm) resulting from the pi-electron donor-acceptor noncovalent interaction.
• A [2]Catenane and a [2]Rotaxane as Prototypes of Topological and Euclidean Molecular “Rubber Gloves”
  作者：Jean-Claude Chambron、Jean-Pierre Sauvage、Kurt Mislow、André De Cian、Jean Fischer

  DOI：10.1002/1521-3765(20011001)7:19<4085::aid-chem4085>3.0.co;2-m

  日期：2001.10.1

  molecules the "rubber glove" property. However, while the molecular graph (constitutional formula) of the [2]rotaxane can be deformed into a planar and, hence, rigidly achiral representation, a feature shared by a few other compounds in the literature that have been characterized as "Euclidean rubber gloves", the molecular graph of the [2]catenane cannot be deformed in this way. It therefore has the unique

  [2] catenane和[2] rotaxane已通过C2对称的2,9-二苯基-1,10-菲咯啉基（dpp基）大环化合物通过1,5-二氧萘亚基的结合而制得。过渡金属模板化技术。在链烷烃的情况下，该大环与基于dpp的大环互锁，该环通过对甲苯基取代基在菲咯啉亚基的4位上定位。在轮烷的情况下，C2对称大环被连接到一个定向的哑铃状分子上，该分子基于相同的4-对甲苯基-1,10-菲咯啉亚基，该亚基带有四芳基甲烷塞。这两个物种都是化学非手性分子，但它们完全由不对称的镜像构象组成。因此，构象对映异构化过程仅通过手性途径进行，这些分子具有“橡胶手套”的特性。但是，尽管[2]轮烷的分子图（结构式）可以变形为平面，因此可以刚性地非手性表示，但文献中一些其他化合物具有的特征是“欧几里得橡胶手套”。 ”，[2]联烷烃的分子图不能以这种方式变形。因此，它具有作为化学非手性“拓扑橡胶手套”的独特性能。