Pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaene-4,5,6,10,11,12,16,17,18,22,23,24-dodecol, 2,8,14,20-tetraphenyl- | 512785-41-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: Pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaene-4,5,6,10,11,12,16,17,18,22,23,24-dodecol, 2,8,14,20-tetraphenyl-
• 英文别名: C-phenylcalix[4]pyrogallolarene；tetra(phenyl)pyrogallol[4]arene；C-phenylpyrogallol[4]arene
• CAS: 512785-41-0
• 化学式: C₅₂H₄₀O₁₂
• 分子量: 856.882
• InChiKey: VJFIYRWCURAKHT-HRGSHGMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.19
• 重原子数：
  64.0
• 可旋转键数：
  4.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  242.76
• 氢给体数：
  12.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  Pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaene-4,5,6,10,11,12,16,17,18,22,23,24-dodecol, 2,8,14,20-tetraphenyl- 在 硫酸 作用下， 反应 4.0h， 以82.5%的产率得到
  参考文献：
  名称：

  C-Arylcalix[4]pyrogallolarene Sulfonic Acid: A Novel and Efficient Organocatalyst Material for Biodiesel Production

  摘要：

  摘要 研究了 C-芳基萼片[4]焦氮杂环戊烯磺酸衍生物的合成及其作为生物柴油生产有机催化剂材料的应用。C- 芳基萼[4]焦醛烯烃衍生物是通过两步反应高产制备的：焦醛与芳香醛（即苯甲醛、4-羟基-3-甲氧基苯甲醛和 4-乙氧基-3-甲氧基苯甲醛）缩合，然后与硫酸进行磺化反应。作为生物柴油生产中棕榈酸与甲醇酯化反应的有机催化剂，对它们进行了评估。使用 4 mol% 的 C-4-hydroxy-3-methoxyphenylcalix[4]pyrogallolarene 磺酸，在 65 °C 下反应 4 小时后，生成棕榈酸甲酯的产率高达 91.9%，与在类似条件下用作传统反应催化剂的硫酸的效率相似。不过，与硫酸不同的是，C-4-羟基-3-甲氧基苯基钙[4]焦氮杂环戊烯磺酸可以通过简单的过滤技术回收，因此从工业和环境角度来看，它比硫酸更好。这些结果表明，C-芳基萼[4]焦醛蒈烯磺酸衍生物是棕榈酸甲酯生物柴油生产的一种新型和潜在的有机催化剂。

  DOI：

  10.1246/bcsj.20190275
• 作为产物：
  描述：

  苯甲醛 、 邻苯三酚 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 24.5h， 以80.9%的产率得到Pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaene-4,5,6,10,11,12,16,17,18,22,23,24-dodecol, 2,8,14,20-tetraphenyl-
  参考文献：
  名称：

  二聚体纳米胶囊诱导构象变化。

  摘要：

  通过添加五配位的锌（II）配合物迫使诱导的顺式-反式-反式（rctt）椅向锥体结构重排，克服了热力学和动力学因素，从而产生了第一个被苯基取代的锌二聚体纳米胶囊。

  DOI：

  10.1039/b921911k

文献信息

• Synthesis and Structural Chemistry of a Ternary Calix[4]arene Lattice Inclusion System
  作者：Solhe F. Alshahateet

  DOI：10.1007/s10870-009-9632-y

  日期：2010.3

  A ternary calix[4]arene lattice inclusion system 3 has been synthesized, characterized and its crystal structure was determined by single crystal X-ray diffraction study. 3 is orthorhombic, space group Pbca with a = 21.236(3) Å, b = 12.2820(16) Å, c = 25.795(3) Å, α = 90°, β = 90°, γ = 90° and Z = 4. Analyses of single crystals of arene 3 crystallized from DMSO revealed the existence of a ternary system

  合成、表征了三元杯[4]芳烃晶格包裹体系统3，并通过单晶X射线衍射研究确定了其晶体结构。3 是正交的，空间群 Pbca，a = 21.236(3) Å，b = 12.2820(16) Å，c = 25.795(3) Å，α = 90°，β = 90°，γ = 90°，Z = 4 . 对从 DMSO 结晶的芳烃 3 单晶的分析揭示了 3 与 DMSO 和 H2O 的三元系统的存在。化合物 3 以重叠形式而不是交错形式存在。观察和分析了不同类型的主-主、主-客和客-客相互作用。图形摘要分析了三元杯[4]芳烃晶格包合体系的结构化学，并观察到了有趣的超分子基序。
• Experimental Comparative Study of Dynamic Behavior in Solution Phase of C-Tetra(phenyl)resorcin[4]arene and C-Tetra(phenyl)pyrogallol[4]arene
  作者：José Luis Casas-Hinestroza、Miguel Ángel Vela Suazo、Mauricio Maldonado Villamil

  DOI：10.3390/molecules25102275

  日期：——

  phenyl-resorcinarenes and pyrogallolarenes is known to produce a conformational mixture of cone and chair isomers. Depending on the synthesis conditions the composition of the conformational mixture is variable; however, the cone conformer is the greatest proportion of phenyl-resorcin[4]arenes and chair conformer of pyrogallol[4]arenes. The experimental evidence suggests that phenyl-substituted resorcinarene

  已知苯基-间苯二酚和焦没食子芳烃的合成会产生锥体和椅式异构体的构象混合物。根据合成条件，构象混合物的组成是可变的；然而，锥形构象异构体是苯-间苯二酚[4]芳烃和连苯三酚[4]芳烃椅子构象异构体的最大比例。实验证据表明，苯基取代的间苯二酚和焦没食子芳烃在溶液中以动态船的形式存在。
• Inclusion complexation between neurotransmitters with polyacetylated calix[4]pyrogallolarenes: 1H-NMR and crystallographic analysis
  作者：José Luis Casas-Hinestroza、Adrián Pérez-Redondo、Mauricio Maldonado

  DOI：10.1007/s11164-022-04735-4

  日期：2022.7

  Complexation between choline and betaine with acetylated calix[4]pyrogallolarenes was studied in DMSO via 1H-NMR spectroscopy and in the gas phase via electrospray ionization-mass spectrometry (ESI–MS). In the presence of acetylated calix[4]pyrogallolarene, especially if there is an alkyl chain on the lower rim of macrocycle, the formation of a very stable host–guest-type complex was observed. In this way, it was found that the affinity constant between O-acylated-tetra(propyl)calix[4]pyrogallolarene with choline or betaine was 45 or 135, respectively, however the complexation process with acetylated calix[4]pyrogallolarene with aromatic substituent on the lower rim, the results showed that there was a weak interaction with the studied neurotransmitters. From the results, the important role played by the acetyl group in the host–guest interaction with betaine was evident. By contrast, the values of the binding constants of choline were not any higher than unmodified calix[4]pyrogallolarenes. Suitable crystals of O-acylated-tetra(propyl)calix[4]pyrogallolarene were obtained and were characterized through an X-ray crystal structure determination and showed the formation of the inclusion complex O-acylated-tetra(propyl) calix[4]pyrogallolarene·DMSO, which crystallized with two additional molecules of dimethylsulfoxide, additionally the DRX data allowing us to establish that the conformation that it has is of a boat and that it is possibly retained in solution.

  通过 1H-NMR 光谱法研究了胆碱和甜菜碱与乙酰化钙[4]焦醛烯烃在二甲基亚砜（DMSO）中的络合情况，并通过电喷雾离子化质谱法（ESI-MS）研究了它们在气相中的络合情况。在乙酰化钙[4]焦咯烷的存在下，尤其是在大环的下缘有烷基链的情况下，观察到形成了非常稳定的主-客型复合物。由此发现，O-乙酰化-四（丙基）萼[4]焦咯烷与胆碱或甜菜碱的亲和力常数分别为 45 或 135，但在与下缘带有芳香取代基的乙酰化萼[4]焦咯烷的络合过程中，结果表明与所研究的神经递质存在微弱的相互作用。结果表明，乙酰基在与甜菜碱的主客体相互作用中发挥了重要作用。相比之下，胆碱的结合常数值并不比未修饰的钙[4]焦铝烯高。我们获得了 O-乙酰化-四（丙基）钙[4]焦醛烯的合适晶体，并通过 X 射线晶体结构测定对其进行了表征，结果显示形成了包合复合物 O-乙酰化-四（丙基）钙[4]焦醛烯-DMSO，该复合物结晶时含有两个额外的二甲基亚砜分子，此外，我们还通过 DRX 数据确定了该复合物的构象为船形，并有可能保留在溶液中。
• Microwave-assisted synthesis of resorcin[4]arene and pyrogallol[4]arene macrocycles
  作者：Muriel Funck、Daniel P. Guest、Gareth W.V. Cave

  DOI：10.1016/j.tetlet.2010.09.115

  日期：2010.12

  A series of resorcin[4]arene and pyrogallol[4]arene macrocycles have been synthesized efficiently within 5 min, affording crystalline products suitable for single crystal X-ray diffraction, utilising microwave irradiation in a 'one-pot' reaction whilst controlling the selective formation of the rccc cone stereoisomer. (C) 2010 Elsevier Ltd. All rights reserved.