Tridecacyclo[27.17.5.56,24.412,41.418,35.17,11.113,17.119,23.130,34.136,40.142,46.147,51.164,68]doheptaconta-7(71),8,10,13(70),14,16,19,21,23(69),30(63),31,33,36,38,40(58),42,44,46(53),47(52),48,50,64,66,68(72)-tetracosaene-8,10,14,16,20,22,31,33,37,39,43,45,48,50,65,67-hexadecol | 1393888-62-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: Tridecacyclo[27.17.5.56,24.412,41.418,35.17,11.113,17.119,23.130,34.136,40.142,46.147,51.164,68]doheptaconta-7(71),8,10,13(70),14,16,19,21,23(69),30(63),31,33,36,38,40(58),42,44,46(53),47(52),48,50,64,66,68(72)-tetracosaene-8,10,14,16,20,22,31,33,37,39,43,45,48,50,65,67-hexadecol
• 英文别名: tridecacyclo[27.17.5.56,24.412,41.418,35.17,11.113,17.119,23.130,34.136,40.142,46.147,51.164,68]doheptaconta-7(71),8,10,13(70),14,16,19,21,23(69),30(63),31,33,36,38,40(58),42,44,46(53),47(52),48,50,64,66,68(72)-tetracosaene-8,10,14,16,20,22,31,33,37,39,43,45,48,50,65,67-hexadecol
• CAS: 1393888-62-4
• 化学式: C₇₂H₇₂O₁₆
• 分子量: 1193.35
• InChiKey: KADPHXOOHBRROY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.8
• 重原子数：
  88
• 可旋转键数：
  0
• 环数：
  14.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  324
• 氢给体数：
  16
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  Tridecacyclo[27.17.5.56,24.412,41.418,35.17,11.113,17.119,23.130,34.136,40.142,46.147,51.164,68]doheptaconta-7(71),8,10,13(70),14,16,19,21,23(69),30(63),31,33,36,38,40(58),42,44,46(53),47(52),48,50,64,66,68(72)-tetracosaene-8,10,14,16,20,22,31,33,37,39,43,45,48,50,65,67-hexadecol 、 二氯磷酸苯酯 在 1-甲基吡咯烷 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以11%的产率得到
  参考文献：
  名称：

  Rim-to-Rim-Connected Homoditopic Biscavitands 客体结合的变构

  摘要：

  合成了边缘到边缘连接的膦酸酯双腔体 1a 和 1b。晶体结构分析和变温 NMR 光谱研究表明，1a 的构象比 1b 更刚性。Biscavitands 1a 和 1b 通过氢键和 CH-π 相互作用与阳离子客体 G1-G3 结合，分别表现出正和负变构效应。客体结合的变构效应与 1a 和 1b 的构象灵活性有关。1a 的正变构效应是由紧密连接的空腔引导的，其中第一个客体结合的信息被转移到剩余的空腔，该空腔变得预先组织。相比之下，在更灵活的 1b 中发现了轻微的负面变构效应。

  DOI：

  10.1002/ejoc.201600410
• 作为产物：
  描述：

  己二醛 、 间苯二酚 在 盐酸 作用下， 以 甲醇 为溶剂， 以11%的产率得到Tridecacyclo[27.17.5.56,24.412,41.418,35.17,11.113,17.119,23.130,34.136,40.142,46.147,51.164,68]doheptaconta-7(71),8,10,13(70),14,16,19,21,23(69),30(63),31,33,36,38,40(58),42,44,46(53),47(52),48,50,64,66,68(72)-tetracosaene-8,10,14,16,20,22,31,33,37,39,43,45,48,50,65,67-hexadecol
  参考文献：
  名称：

  脚到脚连接的双间苯二碳氮烷的合成与结构

  摘要：

  以极高的收率获得了双resorcinarenenes 1a – d，最后以50％的收率获得了1e。X射线衍射分析表明1a和1b呈螺旋构象，而1c – e的两个间苯二芳烃呈平行方向，其中脂族链的裂口截留了一个或两个溶剂分子。构象研究表明（P）-和（M）-螺旋构象体之间的螺旋相互转化取决于脂族链的长度。1a在螺旋互变中具有最大的能量屏障，而在1b中，其更灵活的脂族链降低了其能量屏障。1a的P / M互变与两个间苯二芳烃的环间氢键的顺时针/逆时针互变耦合。较大的负熵贡献表明过渡态最有可能比基态更有序，这表明过渡态最有可能是对称的并且被水分子溶剂化。在M06-2 X / 6-31G（d，p）水平进行的计算表明，更稳定的（P）构型在两个间苯二碳氢芳烃之间具有顺时针的环间氢键。

  DOI：

  10.1021/acs.joc.7b02301

文献信息

• Modified Synthesis and Supramolecular Polymerization of Rim-to-Rim Connected Bisresorcinarenes
  作者：Hitomi Yamada、Toshiaki Ikeda、Tsutomu Mizuta、Takeharu Haino

  DOI：10.1021/ol301996q

  日期：2012.9.7

  The acid-catalyzed condensation reaction of resorcinol and bisdimethoxyacetals gave rise to rim-to-rim connected bisresorcinarenes in good yields. In the presence of ethanol, the homoditopic bisresorcinarenes assembled to form supramolecular polymers via hydrogen bonding interactions. The fibrous morphologies of the supramolecular polymers were confirmed by atomic force microscopy and scanning electron microscopy.
• Conformational Characteristics of Feet-to-Feet-Connected Biscavitands
  作者：Daisuke Shimoyama、Takeharu Haino

  DOI：10.1021/acs.joc.9b01730

  日期：2019.11.1

  X-ray crystallography of an acetoxy-protected bisresorcinarene and biscavitands possessing phosphonate and dialkylsilyl bridges revealed that the bisresorcinarene and the biscavitands adopt helical forms in the solid state. Helical conformations were also found in solution. The helix-helix interconversions of the biscavitands occurred with high activation barriers of more than 50 kJ mol(-1). The activation parameters of the helix-helix interconversions were determined using exchange spectroscopy (EXSY). The positive activation enthalpies and the negative activation entropies suggest that the transition states of the helix-helix interconversion process are most likely more strained and symmetric than the ground states. The compensatory enthalpy-entropy correlation is found in the series of activation parameters, giving rise to a compensation temperature of 254 K.
• Negative Cooperativity in Guest Binding of a Ditopic Self-Folding Biscavitand
  作者：Haruna Fujimoto、Daisuke Shimoyama、Katsuo Katayanagi、Naomi Kawata、Takehiro Hirao、Takeharu Haino

  DOI：10.1021/acs.orglett.1c01837

  日期：2021.8.20
• Allostery in Guest Binding of Rim-to-Rim-Connected Homoditopic Biscavitands
  作者：Daisuke Shimoyama、Hitomi Yamada、Toshiaki Ikeda、Ryo Sekiya、Takeharu Haino

  DOI：10.1002/ejoc.201600410

  日期：2016.7

  synthesized. Crystal structure analysis and variable-temperature NMR spectroscopy studies reveal that 1a is more rigid in conformation than 1b. Biscavitands 1a and 1b bind cationic guests G1–G3 through hydrogen bonding and CH–π interactions, demonstrating positive and negative allosteric effects, respectively. The allosteric effects in guest binding are associated with the conformational flexibilities of

  合成了边缘到边缘连接的膦酸酯双腔体 1a 和 1b。晶体结构分析和变温 NMR 光谱研究表明，1a 的构象比 1b 更刚性。Biscavitands 1a 和 1b 通过氢键和 CH-π 相互作用与阳离子客体 G1-G3 结合，分别表现出正和负变构效应。客体结合的变构效应与 1a 和 1b 的构象灵活性有关。1a 的正变构效应是由紧密连接的空腔引导的，其中第一个客体结合的信息被转移到剩余的空腔，该空腔变得预先组织。相比之下，在更灵活的 1b 中发现了轻微的负面变构效应。
• Synthesis and Structure of Feet-to-Feet Connected Bisresorcinarenes
  作者：Daisuke Shimoyama、Toshiaki Ikeda、Ryo Sekiya、Takeharu Haino

  DOI：10.1021/acs.joc.7b02301

  日期：2017.12.15

  helical conformations, whereas the two resorcinarenes of 1c–e were in parallel orientations in which the clefts of the aliphatic chains entrapped one or two solvent molecules. The conformational study revealed that the helix interconversion between the (P)- and (M)-helical conformers depended on the length of the aliphatic chains. 1a had the largest energetic barrier to helix interconversion, while

  以极高的收率获得了双resorcinarenenes 1a – d，最后以50％的收率获得了1e。X射线衍射分析表明1a和1b呈螺旋构象，而1c – e的两个间苯二芳烃呈平行方向，其中脂族链的裂口截留了一个或两个溶剂分子。构象研究表明（P）-和（M）-螺旋构象体之间的螺旋相互转化取决于脂族链的长度。1a在螺旋互变中具有最大的能量屏障，而在1b中，其更灵活的脂族链降低了其能量屏障。1a的P / M互变与两个间苯二芳烃的环间氢键的顺时针/逆时针互变耦合。较大的负熵贡献表明过渡态最有可能比基态更有序，这表明过渡态最有可能是对称的并且被水分子溶剂化。在M06-2 X / 6-31G（d，p）水平进行的计算表明，更稳定的（P）构型在两个间苯二碳氢芳烃之间具有顺时针的环间氢键。