25,27-dipropoxythiacalix[4]arene | 386213-92-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 25,27-dipropoxythiacalix[4]arene
• 英文别名: 26,28-Dipropoxy-2,8,14,20-tetrathiapentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaene-25,27-diol
• CAS: 386213-92-9；841261-64-1；949908-22-9
• 化学式: C₃₀H₂₈O₄S₄
• 分子量: 580.814
• InChiKey: VCMPGPNZLKZDAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  38
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  160
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  25,27-dipropoxythiacalix[4]arene 在 溴 作用下， 以 氯仿 为溶剂， 反应 24.0h， 以90%的产率得到5,11,17,23-Tetrabromo-26,28-dipropoxy-2,8,14,20-tetrathiapentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaene-25,27-diol
  参考文献：
  名称：

  Upper rim substitution of thiacalix[4]arene

  摘要：

  Upper rim bromination of thiacalix[4]arene has been achieved for the first time using a distally disubstituted thiacalix[4]arene as a starting material. Depending on the bromine:thiacalix[4]arene ratios, the corresponding dibromo- and tetrabromo derivatives were obtained which opens the door for subsequent derivatisation of the upper rim of thiacalix[4]arenes. Interestingly, direct bromination of tetraalkylated compounds did not yield brominated derivatives. The structure of the tetrabromo derivative in the 1.3-alternative conformation was proven by X-ray crystallography. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01461-7
• 作为产物：
  描述：

  1-碘代丙烷 、 25,26,27,28-tetrahydroxy-2,8,14,20-tetrathiacalix[4]arene 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 168.0h， 生成 25,27-dipropoxythiacalix[4]arene
  参考文献：
  名称：

  基于脲基取代的硫杂杯[4]芳烃和杯[4]芳烃的阴离子受体

  摘要：

  25,27-二丙氧基硫杂杯[4]芳烃的区域选择性硝化是合成在上部边缘带有两个芳基脲基官能团的硫杂杯[4]芳烃衍生物的关键步骤。使用噻唑杯[4]芳烃/杯[4]芳烃部分作为分子支架的脲基单元的预组织产生了新的阴离子受体。这些化合物尽管基于氢键相互作用，但即使在具有高HB竞争性的溶剂（如DMSO）中也显示出良好的络合能力。在其他方面相同的结构6a和7a的直接比较显示，在阴离子结合方面，噻唑杯[4]亚芳基衍生物比其经典类似物具有显着优势。

  DOI：

  10.1016/j.tet.2008.08.030

文献信息

• Partially O-Alkylated Thiacalix[4]arenes:  Synthesis, Molecular and Crystal Structures, Conformational Behavior
  作者：Hana Dvořáková、Jan Lang、Jiří Vlach、Jan Sýkora、Michal Čajan、Michal Himl、Michaela Pojarová、Ivan Stibor、Pavel Lhoták

  DOI：10.1021/jo070927i

  日期：2007.9.1

  3a adopt the cone conformation in solution, distally disubstituted compounds 1b, 1‘b, 2b, 2‘b, 3b, and 3‘b exhibit several interesting conformational features. They prefer pinched cone conformation in solution, and, except for 3‘b, they form also 1,2-alternate conformation, which is flexible and undergoes rather fast transition between two identical structures. The crystal structures of the compounds

  核磁共振波谱，X射线衍射分析和量子化学计算被用于在下部边缘带有甲基（1），乙基（2）或丙基（3）基团的部分烷基化的硫杂杯[4]芳烃的构象行为研究。构象性质受两个基本作用支配：（i）通过分子内氢键的稳定作用，和（ii）在较低边缘的烷氧基的空间要求。尽管单取代的衍生物1A和3a中采用在溶液中，二取代的远侧化合物锥形构象1B，1 “ b，2B，2 ” b，图3b，和3 ' b表现出了一些有趣的构象特征。他们更喜欢捏锥形构象在溶液中，并且，除了3 ' b，它们也形成1,2-交替构象，这是两个相同的结构之间的柔性并经历相当快的过渡。的化合物的晶体结构1B，2B，2 ' b，和图3b显示又相当罕见1,2-交替构形成通过π-π相互作用维持在一起的分子通道。具有六角对称性的不同通道，宽度为0.26 nm在3b的收缩锥构象的晶体结构中形成了α- δ。一种不常见的氢键模式是在二甲氧基和二丙氧基衍生物发现1 “
• Anion receptors based on ureido-substituted thiacalix[4]arenes and calix[4]arenes
  作者：Jan Kroupa、Ivan Stibor、Michaela Pojarová、Marcela Tkadlecová、Pavel Lhoták

  DOI：10.1016/j.tet.2008.08.030

  日期：2008.10

  as a key step in the synthesis of thiacalix[4]arene derivative bearing two arylureido functions on the upper rim. The preorganisation of ureido units using the thiacalix[4]arene/calix[4]arene moieties as a molecular scaffold gave novel anion receptors. These compounds, albeit based on hydrogen bonding interactions, show good complexation ability even in highly HB-competitive solvent, such as DMSO.

  25,27-二丙氧基硫杂杯[4]芳烃的区域选择性硝化是合成在上部边缘带有两个芳基脲基官能团的硫杂杯[4]芳烃衍生物的关键步骤。使用噻唑杯[4]芳烃/杯[4]芳烃部分作为分子支架的脲基单元的预组织产生了新的阴离子受体。这些化合物尽管基于氢键相互作用，但即使在具有高HB竞争性的溶剂（如DMSO）中也显示出良好的络合能力。在其他方面相同的结构6a和7a的直接比较显示，在阴离子结合方面，噻唑杯[4]亚芳基衍生物比其经典类似物具有显着优势。
• Convenient Direct Syntheses of Selectively para-Substituted Di-, Tri- and Tetra-Formylated Thiacalix[4]arenes
  作者：Weiping Yang、Wei Wang、Rong Guo、Linbo Gong、Shuling Gong

  DOI：10.1002/ejoc.201200252

  日期：2012.6

  thiacalix[4]arenes substituted on the para positions is described. Di- and triformylated thiacalix[4]arenes were obtained by formylation of partially propyl- or benzoyl-substituted thiacalix[4]arenes. Complete para-formylation was successfully achieved by formylation and dealkylation of tetraisopropoxythiacalix[4]arene conformers in one step. This experimental procedure is a simpler synthesis for completely

  描述了对位取代的硫杯 [4] 芳烃的二、三和四甲酰化的有效直接方法。二甲酰化和三甲酰化的硫代杯[4]芳烃是通过部分丙基或苯甲酰基取代的硫代杯[4]芳烃的甲酰化获得的。通过四异丙氧基硫代杯[4]芳烃构象异构体的甲酰化和脱烷基化，一步成功地实现了完全的对甲酰化。与之前报道的溴化硫代杯 [4] 芳烃的间接方法相比，该实验程序对于完全甲酰化的硫代杯 [4] 芳烃来说是一种更简单的合成方法。
• ‘Honeycomb’ nanotube assembly based on thiacalix[4]arene derivatives by weak interactions
  作者：Wei Wang、Weiping Yang、Rong Guo、Shuling Gong

  DOI：10.1039/c5ce01088h

  日期：——

  with π⋯π stacking interactions, while 12·CHCl3 forms a novel head-to-head dimer motif and its infinite network structures are stabilised by Cl⋯Cl, Cl⋯π and CN⋯Cl interactions. Although 10·H2O does not form a head-to-head dimer, it has taken on a new cubic close packing (ccp) arrangement, forming a water channel nanotube. X-ray single-crystal diffraction studies reveal that the weak interactions, including

  二-氧-丙氧基-单甲酰基-硫杂杯[4]芳烃·氯仿（7 · CHCl 3），二-氧-丙氧基-二甲酰基-硫杂杯[4]芳烃（8），二-O的晶体结构-丙氧基-三甲酰基-硫杂杯[4]芳烃（9），二-O-苯甲酚-二甲酰基-硫杂杯[4]芳烃·水（10 · H 2 O），单-O-丙氧基-三甲酰基-thiacalix [4] arene（11）和二-O-丙氧基-二氰基-thiacalix [4] arene·chloroform（12 · CHCl 3）在相同的结晶介质中进行了研究。这些晶体形成相似的“蜂窝”纳米管结构，并在固态下显示不同的组件。7 ·氯仿3，8，9和11装配到“经典的”头-头二聚体通过与π⋯π堆积相互作用的芳香环的交错，而12种·氯仿3形式的新颖头-头二聚体基序及其Cl⋯Cl，Cl⋯π和CN⋯Cl相互作用稳定了无限的网络结构。虽然10 · H 2 O它没有形成头对头的二聚体，而是采用了新的
• Stereoselective alkylation of thiacalix[4]arenes
  作者：Michal Himl、Michaela Pojarová、Ivan Stibor、Jan Sýkora、Pavel Lhoták

  DOI：10.1016/j.tetlet.2004.11.077

  日期：2005.1

  A direct tetraalkylation of thiacalix[4]arenes using procedures well established in 'classical' calixarene chemistry usually gives the 1,3-alternate conformers as the main product (n-PrI/K2CO3/acetone) while the cone conformers are obtained only in very poor yields (n-PrI/NaH/DMF). Surprisingly, the so far almost inaccessible cone conformers can be prepared in high yields using the two-step procedure: dialkylation-dialkylation, opening the way for their further utilisation in supramolecular chemistry. (C) 2004 Elsevier Ltd. All rights reserved.