1,3-Calix[5]crown-5 | 176298-42-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3-Calix[5]crown-5
• 英文别名: 3,9,15,21,42-pentatert-butyl-25,28,31,34,37-pentaoxaheptacyclo[21.15.7.17,11.113,17.140,44.05,38.019,24]octatetraconta-1,3,5(38),7,9,11(48),13(47),14,16,19(24),20,22,40,42,44(46)-pentadecaene-46,47,48-triol
• CAS: 176298-42-3
• 化学式: C₆₃H₈₄O₈
• 分子量: 969.355
• InChiKey: NAEJGJHXMGOCFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.2
• 重原子数：
  71
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  107
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  氯甲烷 、 1,3-Calix[5]crown-5 在 cesium fluoride 作用下， 以 四氢呋喃 为溶剂， 生成 3,9,15,21,42-pentatert-butyl-48-methoxy-25,28,31,34,37-pentaoxaheptacyclo[21.15.7.17,11.113,17.140,44.05,38.019,24]octatetraconta-1(38),2,4,7,9,11(48),13,15,17(47),19,21,23,40,42,44(46)-pentadecaene-46,47-diol
  参考文献：
  名称：

  杯[5]冠的固有手性衍生物

  摘要：

  描述了分别到达手性（1,3）-和（1,2）-杯[5]冠醚2和3的互补合成途径。O-烷基残基的区域和立体化学排列通过NMR推论得出，并由Crown-5衍生物3b的单晶X射线分析进一步证实。

  DOI：

  10.1016/0040-4039(96)00048-2
• 作为产物：
  描述：

  四乙二醇二对甲苯磺酸酯 、 4-叔丁基杯[5]芳烃 在 cesium fluoride 作用下， 生成 1,3-Calix[5]crown-5
  参考文献：
  名称：

  Regioselective synthesis of calixcrowns derived from p-tert-butylcalix[5]arene

  摘要：

  Alkylation of p-tert-butylcalix[5]arene with oligoethylene glycol-ditosylates in the presence of CsF affords the 1,3-bridged calix[5]crowns la-c in 51 to 72% yield. In the case of hexaethylene glycol the isomeric 1,2-bridged calix[5]crown-7 2c was obtained additionally. The calixcrowns were further modified by alkylation of the remaining hydroxyl groups.

  DOI：

  10.1016/s0040-4020(01)87186-6

文献信息

• Crown ether derivatives of calix[5]arenes: synthesis and complexation properties
  作者：Françoise Arnaud-Neu、Ralf Arnecke、Volker Böhmer、Stefano Fanni、James L. M. Gordon、Marie-José Schwing-Weill、Walter Vogt

  DOI：10.1039/p29960001855

  日期：——

  Several crown ether derivatives of calix[5]- and tert-butylcalix[5]-arene have been synthesized and converted into their trimethyl ethers as neutral ligands. For selected examples extraction studies have been carried out with alkali metal picrates in the system water–dichloromethane and stability constants have been determined by UV spectroscopy in methanol. All ligands show a more or less pronounced

  已合成了杯[5]-和叔丁基杯[5]-芳烃的几种冠醚衍生物，并将其转化为中性配体的三甲基醚。对于选定的实例，已经在水-二氯甲烷系统中用碱金属苦味酸盐进行了萃取研究，并通过紫外光谱法在甲醇中确定了稳定性常数。所有的配体或多或少都显示出对较大的碱金属阳离子的偏爱。叔丁基杯杯[5]芳烃的Crown-5衍生物对Cs +对Na +的选择性最高（S = 630）。量热滴定法表明络合是由焓和熵驱动的。
• Cacciapaglia, Roberta; Mandolini, Luigi; Arnecke, Ralf, Journal of the Chemical Society. Perkin Transactions 2 (2001), 1998, # 2, p. 419 - 423
  作者：Cacciapaglia, Roberta、Mandolini, Luigi、Arnecke, Ralf、Boehmer, Volker、Vogt, Walter

  DOI：——

  日期：——
• Inherently chiral derivatives of calix[5]crowns
  作者：Ralf Arnecke、Volker Böhmer、George Ferguson、Sebastiano Pappalardo

  DOI：10.1016/0040-4039(96)00048-2

  日期：1996.2

  Complementary synthetic routes to the chiral (1,3)- and (1,2)-calix[5]crown ethers 2 and 3, respectively, are described. The regio- and stereochemical arrangement of the O-alkyl residues is deduced by NMR, and further supported by a single-crystal X-ray analysis of crown-5 derivative 3b.

  描述了分别到达手性（1,3）-和（1,2）-杯[5]冠醚2和3的互补合成途径。O-烷基残基的区域和立体化学排列通过NMR推论得出，并由Crown-5衍生物3b的单晶X射线分析进一步证实。
• Regioselective synthesis of calixcrowns derived from p-tert-butylcalix[5]arene
  作者：Dagmar Kraft、Ralf Arnecke、Volker Böhmer、Walter Vogt

  DOI：10.1016/s0040-4020(01)87186-6

  日期：1993.7

  Alkylation of p-tert-butylcalix[5]arene with oligoethylene glycol-ditosylates in the presence of CsF affords the 1,3-bridged calix[5]crowns la-c in 51 to 72% yield. In the case of hexaethylene glycol the isomeric 1,2-bridged calix[5]crown-7 2c was obtained additionally. The calixcrowns were further modified by alkylation of the remaining hydroxyl groups.