25,26,27,28-tetrapropoxycalix[4]arene | 1071466-33-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 25,26,27,28-tetrapropoxycalix[4]arene
• 英文别名: 25,26,27,28-Tetra(propan-2-yloxy)pentacyclo[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；25,26,27,28-tetra(propan-2-yloxy)pentacyclo[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
• CAS: 1071466-33-5
• 化学式: C₄₀H₄₈O₄
• 分子量: 592.819
• InChiKey: JGLKJHIZMBFIND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.8
• 重原子数：
  44
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  25,26,27,28-tetrapropoxycalix[4]arene 在 sodium nitrate 、 tin(II) chloride dihdyrate 、 溶剂黄146 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 16.5h， 生成 12,32,52,72-tetraisopropoxy-1,3,5,7(1,3)-tetrabenzenacyclooctaphane-15,55-diamine
  参考文献：
  名称：

  Anion complexation by calix[4]arene–TTF conjugates

  摘要：

  Calix[4]arenes bearing tetrathiafulvalene (TTF) moieties appended to the upper rim via the amidic functions were synthesized and used for H-1 NMR and UV/Vis complexation studies towards selected anions. It was found that the complexation affinity towards H2PO4- dramatically depends on the substitution pattern of the calixarene moiety. As a result, the proximally disubstituted derivative has a complexation constant by two orders of magnitude higher than the distally disubstituted analogue. The differences between proximal and distal receptors were also documented by their behaviour during the oxidation of the attached TTF units. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2011.06.001
• 作为产物：
  描述：

  杯[4]芳烃 、 2-溴丙烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以80%的产率得到25,26,27,28-tetrapropoxycalix[4]arene
  参考文献：
  名称：

  Regioselective upper-rim functionalizations of calix[4]arene by diphenylphosphino groups

  摘要：

  对calix[4]arene的上缘选择性官能化已经进行，以制备所有多取代二苯基膦衍生物。此外，已确定了5,17-二溴-11,23-双(二苯基膦基)-25,26,27,28-四-n-丙氧基calix[4]arene和5,11,17,23-四(二苯基膦基)-25,26,27,28-四异丙氧基calix[4]arene的X射线结构。通过适当选择碱、烷基锂-溶剂系统、化学计量、反应时间等方法实现了选择性官能化。开发了一种新的便捷方法，可在相对较大规模上选择性地制备calix[4]arenes的衍生物，涉及将远端二酯衍生物转酯化为近端异构体。关键词：calix[4]arenes、膦、上缘、X射线结构、转酯化。

  DOI：

  10.1139/v01-161

文献信息

• The selective dealkylations: the formylations of the three easily accessible calix[4]arene conformers immobilized by propyl and isopropyl groups
  作者：Weiping Yang、Rong Guo、Wei Wang、Shuling Gong

  DOI：10.1016/j.tetlet.2012.02.061

  日期：2012.4

  accessible calix[4]arene conformers immobilized by four propyl or isopropyl groups by Duff reaction. Propyl group led to exhaustively formylated products due to the weak steric hinderance effect. While as for the isopropoxy calix[4]arenes, with the increase of steric hinderance, 1,3-alternate conformer gave exhaustively formylated product with no alkyl group dealkylating; partial cone conformer gave the

  甲酰基被引入对位通过Duff反应固定在四个丙基或异丙​​基上的三个容易获得的杯[4]芳烃构象异构体的位置。由于弱的位阻作用，丙基基团导致了彻底的甲酰化产物。至于异丙氧基杯[4]芳烃，随着位阻的增加，1,3-交替构象异构体给出的是甲酰化产物，没有烷基脱烷基。部分圆锥构象异构体以1，3-交替构象得到四甲酰化的近端A，B-二醚；且视锥构象异构体产生三甲酰化衍生物，并伴有三个或两个直链烷基的选择性脱烷基。结果表明，起始化合物的空间位阻效应极大地影响了产物的结构。
• Calix[4]arene Having a Convergent Carboxylic Acid Function: Synthesis and Ion Binding Properties of a New Cs⁺-selective Ionophore
  作者：Hyun Jae Cho、Ji Young Kim、Suk-Kyu Chang

  DOI：10.1246/cl.1999.493

  日期：1999.6

  Calix[4]arene bearing a convergent carboxylic acid function employing the Kemp’s triacid motif exhibited a pronounced selective ionophoric behavior toward Cs+ over other alkali metal ions. The selectivities of calix[4]arene-acid for Cs+ over Rb+, K+, and Na+ ions assessed by competitive transport experiments were 7.9, 26, and 121, respectively.

  钙[4]炔具有会聚羧酸功能，采用坎普三酸结构，对 Cs+ 而非其他碱金属离子具有明显的选择性离子亲和性。通过竞争性迁移实验评估，钙[4]炔酸对 Cs+的选择性分别为 7.9、26 和 121，而对 Rb+、K+ 和 Na+离子的选择性则分别为 7.9、26 和 121。
• Anion recognition by calix[4]arene-based p-nitrophenyl amides
  作者：Karolína Flídrová、Marcela Tkadlecová、Kamil Lang、Pavel Lhoták

  DOI：10.1016/j.tetlet.2011.11.127

  日期：2012.2

  Calix[4]arene derivatives immobilised in the cone conformation and bearing p-nitrophenyl moieties appended to the upper rim via the amide functions have been synthesised and applied as anion receptors. The H-1 NMR and UV/Vis complexation studies towards selected anions proved that the complexation ability depends considerably on the substitution pattern of the calixarene core. Thus, the proximal diamide derivative has a complexation constant for H2PO4- by one order of magnitude higher than the distal analogue.(C) 2011 Elsevier Ltd. All rights reserved.
• Regioselective upper-rim functionalizations of calix[4]arene by diphenylphosphino groups
  作者：Jonathan Gagnon、Martin Vézina、Marc Drouin、Pierre D Harvey

  DOI：10.1139/v01-161

  日期：2001.10.1

  The regioselective upper-rim functionalization of calix[4]arene have been performed to prepare all the multisubstituted diphenylphosphine derivatives. In addition, the X-ray structures of 5,17-dibromo-11,23-bis(diphenylphosphino)-25,26,27,28-tetra-n-propoxycalix[4]arene and 5,11,17,23-tetrakis(diphenylphosphino)-25,26,27,28-tetra-i-propoxy-calix[4]arene have been determined. Regioselective functionalizations have been achieved using methods that involve appropriate choices of bases, alkyllithium-solvent systems, stoichiometry, and reaction times. A new and convenient method for selectively preparing derivitized calix[4]arenes at proximal positions in relative large scale quantity has been developed and involves a transesterification of the distal diester derivative into the proximal isomer.Key words: calix[4]arenes, phosphine, upper-rim, X-ray structure, transesterification.

  对calix[4]arene的上缘选择性官能化已经进行，以制备所有多取代二苯基膦衍生物。此外，已确定了5,17-二溴-11,23-双(二苯基膦基)-25,26,27,28-四-n-丙氧基calix[4]arene和5,11,17,23-四(二苯基膦基)-25,26,27,28-四异丙氧基calix[4]arene的X射线结构。通过适当选择碱、烷基锂-溶剂系统、化学计量、反应时间等方法实现了选择性官能化。开发了一种新的便捷方法，可在相对较大规模上选择性地制备calix[4]arenes的衍生物，涉及将远端二酯衍生物转酯化为近端异构体。关键词：calix[4]arenes、膦、上缘、X射线结构、转酯化。
• Anion complexation by calix[4]arene–TTF conjugates
  作者：Karolína Flídrová、Marcela Tkadlecová、Kamil Lang、Pavel Lhoták

  DOI：10.1016/j.dyepig.2011.06.001

  日期：2012.1

  Calix[4]arenes bearing tetrathiafulvalene (TTF) moieties appended to the upper rim via the amidic functions were synthesized and used for H-1 NMR and UV/Vis complexation studies towards selected anions. It was found that the complexation affinity towards H2PO4- dramatically depends on the substitution pattern of the calixarene moiety. As a result, the proximally disubstituted derivative has a complexation constant by two orders of magnitude higher than the distally disubstituted analogue. The differences between proximal and distal receptors were also documented by their behaviour during the oxidation of the attached TTF units. (C) 2011 Elsevier Ltd. All rights reserved.