25,26-27,28-biscrown-4-calix<4>arene, cone conformer | 220082-09-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 25,26-27,28-biscrown-4-calix<4>arene, cone conformer
• 英文别名: 25,26-27,28-biscrown-4-calix<4>arene, 1,2-alternate conformer；13,16,19,22,36,39,42,45-Octaoxaheptacyclo[32.12.1.111,24.05,46.07,12.023,28.030,35]octatetraconta-1,3,5(46),7(12),8,10,23(28),24,26,30(35),31,33-dodecaene
• CAS: 220082-09-7
• 化学式: C₄₀H₄₄O₈
• 分子量: 652.785
• InChiKey: SSNFTLPSKHSNFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  48
• 可旋转键数：
  0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  25,26-27,28-biscrown-4-calix<4>arene, cone conformer 在 氯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以100%的产率得到13,16,19,22,36,39,42,45-Octaoxaheptacyclo[32.12.1.111,24.05,46.07,12.023,28.030,35]octatetraconta-1,3,5(46),7(12),8,10,23(28),24,26,30(35),31,33-dodecaene-3,9,26,32-tetrasulfonyl chloride
  参考文献：
  名称：

  Water-soluble para -sulfonated 1,2;3,4-calix[4]arene-biscrowns in the cone conformation

  摘要：

  Water-soluble 1,2:3,4-calix[4]arene-biscrowns (14)-(18) have been synthesized in two or three steps via chlorosulfonation. Cs+-ligand interactions were studied in aqueous media by H-1 NMR. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02399-1
• 作为产物：
  描述：

  杯[4]芳烃 、 三乙二醇二(对甲苯磺酸酯) 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以17%的产率得到25,26-27,28-biscrown-4-calix<4>arene, cone conformer
  参考文献：
  名称：

  Water-soluble para -sulfonated 1,2;3,4-calix[4]arene-biscrowns in the cone conformation

  摘要：

  Water-soluble 1,2:3,4-calix[4]arene-biscrowns (14)-(18) have been synthesized in two or three steps via chlorosulfonation. Cs+-ligand interactions were studied in aqueous media by H-1 NMR. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02399-1

文献信息

• Synthesis of 1,2-bridged calix[4]arene-biscrowns in the 1,2-alternate conformation
  作者：Arturo Arduini、Laura Domiano、Andrea Pochini、Andrea Secchi、Rocco Ungaro、Franco Ugozzoli、Oliver Struck、Willem Verboom、David N Reinhoudt

  DOI：10.1016/s0040-4020(97)00097-5

  日期：1997.3

  New methods to obtain 1,2-bridged calix[4]arene-biscrowns in the 1,2-alternate conformation are described. The stereochemistry of the proximal double functionalization reaction is mainly governed by the solvent, the length of the polyether units and the base used to deprotonate the calix[4]arene.

  描述了获得1,2-交替构象的1,2-桥联杯[4]芳烃-双冠的新方法。近端双官能化反应的立体化学主要由溶剂，聚醚单元的长度和用来使杯[4]芳烃去质子化的碱决定。
• 1,2-Bridged Calix[4]arene Monocrowns and Biscrowns in the 1,2-Alternate Conformation
  作者：George Ferguson、Alan J. Lough、Anna Notti、Sebastiano Pappalardo、Melchiorre F. Parisi、Ada Petringa

  DOI：10.1021/jo9810516

  日期：1998.12.1

  The condensation of 1, 2-di[(2-pyridylmethyl)oxy]calix[4]arenes 1 (R = Bu-t, H) with glycol ditosylates 2a-e in anhydrous toluene in the presence of (BuOK)-Bu-t has led to a mixture of 1,2-alternate and cone 1,2-calix[4]arene crown conformers 3 and 4, respectively. Similarly, the reaction of 1,2-bridged calix[4]arene crown-4 5 with tri- to pentaethylene glycol ditosylates 2a-c has produced 1,2-alternate and cone calix[4]arene biscrown conformers 6 and 7, respectively. The distribution of conformers depends on the para-substituent at the upper rim and the length and bulkiness of the ditosylates. The best yields of the 1,2-alternate conformer (up to 51%) are observed in the absence of tBu groups and with the longer polyether chain. The conformational features of 3 and 6 have been deduced by NMR spectroscopy and by X-ray crystallography. X-ray analysis of 25,26-27,28-biscrown-4-calix[4]arene (6a) shows that there are two independent molecules in the asymmetric unit, both in the 1,2-alternate conformation.