1,3-二丙氧基冠醚 | 161282-96-8

• 物质功能分类: 化学试剂 - 有机试剂 - 冠醚
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1,3-二丙氧基冠醚
• 英文名称: 25,27-bis(2-propyloxy)calix<4>arene-crown-6
• 英文别名: 25,27-bis(2-propoxy)calix<4>arene-crown-6；25,27-di-iso-propoxycalix[4]arene-26,28-crown-6；1,3-diisopropoxycalix[4]arene-26,28-crown-6；1,3-diisopropoxycalix[4]arene-crown-6；1,3-diisopropylcalix[4]arenecrown-6；25,27-bis(2-propyloxy)calix[4]arene-crown-6；43,44-di(propan-2-yloxy)-3,6,9,12,15,18-hexaoxahexacyclo[18.15.7.126,30.137,41.02,32.019,24]tetratetraconta-1(35),2(32),19(24),20,22,26,28,30(44),33,37(43),38,40-dodecaene
• CAS: 161282-96-8；162989-76-6；162301-46-4
• 化学式: C₄₄H₅₄O₈
• 分子量: 710.908
• InChiKey: RKXRMMYNTOHWDA-UHFFFAOYSA-N

物化性质

• 熔点：
  196 °C
• 沸点：
  668.43°C (rough estimate)
• 密度：
  1.0169 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  52
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  8

安全信息

• 海关编码：
  29329900

反应信息

• 作为反应物：
  描述：

  1,3-二丙氧基冠醚 在 硝酸 、 乙酸酐 、 溶剂黄146 、 tin(ll) chloride 作用下， 以 乙醇 为溶剂， 反应 20.0h， 生成 11,23-diamino-25,27-diisopropoxycalix[4]arene-26,28-crown-6
  参考文献：
  名称：

  Synthesis of calixarene–cyclodextrin coupling products

  摘要：

  The coupling of two or four mono-6-amino beta-cyclodextrin (amino-CD) units, (unprotected or permethylated hydroxyls), to diisopropoxycalix[4]arene crown-6 (CAL) was realised using the N,N'-succinyldiamide linker. The resulting molecules in two series were characterised with the help of mass and NMR spectroscopies. The yields of all coupling products were improved for permethylated sugar series compared to the hydroxylated CD series or to our previous studies. The two beta-cyclodextrin (beta-CD) residues coupled to disubstituted CAL were orientated from the same side of the crown ether. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.089
• 作为产物：
  描述：

  二对甲苯磺酸戊乙二醇 在 碘代三甲硅烷 、 sodium hydride 、 caesium carbonate 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 10.0h， 生成 1,3-二丙氧基冠醚
  参考文献：
  名称：

  Synthesis, Complexation, and Membrane Transport Studies of 1,3-Alternate Calix[4]arene-crown-6 Conformers: A New Class of Cesium Selective Ionophores

  摘要：

  1,3-Dialkoxycalix[3]arene-crown-6 ionophores (4a-d) are obtained in the fixed 1,3-alternate conformation in 63-85% yield by the reaction of the corresponding 1,3-dialkoxycalix[4]arenes 3a-d with pentaethylene glycol ditosylate in CH3CN in the presence of Cs2CO3. The corresponding cone conformer of the diisopropyl derivative (6) was synthesized via selective demethylation of the 1,3-dimethoxycalix-crown (2a) and subsequent dialkylation. Extraction experiments with alkali picrates reveal a strong preference of ligands 4 for Cs+. Thermodynamic parameters obtained for the complexation of 4a show that the high stability constant in MeOH (log beta = 6.4 +/- 0.4) is reflected mainly in the large -Delta H-c value of 50.2 +/- 0.2 kJ . mol(-1). The entropy of complexation (T Delta S-c = -15 kJ . mol(-1)), less negative than for other crown ethers, is explained in terms of preorganization of 4a. The X-ray structure of the cesium picrate . 4a complex shows clearly that the cation is positioned between the two aromatic rings with short Cs-C distances of 3.49 and 3.69 Angstrom, respectively. H-1 MMR spectroscopy confirms this type of structure in solution. Ligands 4 incorporated in supported liquid membranes transport Cs+ cations with a high preference over Na+. By the application of an anion gradient, traces of Cs+ can be removed (greater than or equal to 99.8%) from acidic solutions (pH = 0) that contain 4 M of NaNO3.

  DOI：

  10.1021/ja00115a012

文献信息

• Crystallization of cesium complex containing bis(2-propyloxy)calix[4]crown-6 and bis[(trifluoromethyl)sulfonyl]imide
  作者：Taoxiang Sun、Zheming Wang、Xinghai Shen

  DOI：10.1016/j.ica.2012.04.005

  日期：2012.7

  A complex of Cs+ with the calixcrown bis(2-propyloxy)calix[4]crown-6 (BPC6) and bis[(trifluoromethyl)sulfonyl]imide (NTf2-), an anion of ionic liquid (IL), was crystallized in the interface region between n-octanol and water. The compound was characterized by single crystal X-ray diffraction, ESI-MS, FT-IR, TGA and PXRD. Cs+ is coordinated with BPC6 by both the six oxygen atoms of the crown and the cation-pi interactions, and with the anion NTf2- via one oxygen atom of the sulfonyl group. This single crystal explains the good extraction ability of BPC6 to Cs+ and reflects a coordinating interaction of NTf2- with the deficient complex [Cs center dot BPC6](+) during the extraction with an IL as diluent. (C) 2012 Elsevier B.V. All rights reserved.
• Selectivity of Calix[4]arene-crown-6 for Cesium Ion in Ise: Effect of the Conformation
  作者：Carlo. Bocchi、Maria. Careri、Alessandro. Casnati、Giovanni. Mori

  DOI：10.1021/ac00119a005

  日期：1995.12.1

  A new series of calix-crowns were used in ion-selective electrodes with two solvents (dibutyl sebacate and o-nitrophenyl octyl ether), As ionophores, the 1,3-dimethoxy and the three different conformers of the 1,3-diisopropoxycalix[4]arene-crown-6 (i,e,, 1,3-alternate, partial cone, and cone) were considered. Their behavior toward cesium ion was studied in terms of detection limit (DL), sensitivity (S, mV/pCs), and selectivity toward protons, ammonium, alkali, and alkaline earth metal ions, The lowest DL value was obtained for membranes containing the 1,3-diisopropoxy derivative in the 1,3-alternate conformation, To correlate the analytical results with the structural properties of the ligand and with the nature of the polymeric membrane, a multifactor ANOVA with interactions was carried out on selectivities toward univalent and divalent ions, As for the alkali metal ions, a highly significant negative correlation (p < 0.01) between the pK(Cs/M)(pot), values and the ionic radius was found; in addition, for the smaller ions H+, Li+, and Na+, the four ionophores showed higher differences in selectivity than for the larger ions K+ and Rb+ as well as for alkaline earth metal ions, Better results than those previously reported with other ligands in terms of DL (5 x 10(-7) M) and pK(Cs/m)(pot) (4.46) were found for the 1,3-diisopropoxycalix[4]arene-crown-6 in the 1,3-alternate conformation.
• Jankowski, Christopher K.; Dozol; Allain, Polish Journal of Chemistry, 2002, vol. 76, # 5, p. 701 - 711
  作者：Jankowski, Christopher K.、Dozol、Allain、Tabet、Ungaro、Casnati、Vicens、Asfari、Boivin

  DOI：——

  日期：——
• Synthesis of calixarene–cyclodextrin coupling products
  作者：C. Hocquelet、J. Blu、C.K. Jankowski、S. Arseneau、D. Buisson、L. Mauclaire

  DOI：10.1016/j.tet.2006.09.089

  日期：2006.12

  The coupling of two or four mono-6-amino beta-cyclodextrin (amino-CD) units, (unprotected or permethylated hydroxyls), to diisopropoxycalix[4]arene crown-6 (CAL) was realised using the N,N'-succinyldiamide linker. The resulting molecules in two series were characterised with the help of mass and NMR spectroscopies. The yields of all coupling products were improved for permethylated sugar series compared to the hydroxylated CD series or to our previous studies. The two beta-cyclodextrin (beta-CD) residues coupled to disubstituted CAL were orientated from the same side of the crown ether. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis, Complexation, and Membrane Transport Studies of 1,3-Alternate Calix[4]arene-crown-6 Conformers: A New Class of Cesium Selective Ionophores
  作者：Alessandro Casnati、Andrea Pochini、Rocco Ungaro、Franco Ugozzoli、Francoise Arnaud、Stefano Fanni、Marie-Jose Schwing、Richard J. M. Egberink、Feike de Jong、David N. Reinhoudt

  DOI：10.1021/ja00115a012

  日期：1995.3

  1,3-Dialkoxycalix[3]arene-crown-6 ionophores (4a-d) are obtained in the fixed 1,3-alternate conformation in 63-85% yield by the reaction of the corresponding 1,3-dialkoxycalix[4]arenes 3a-d with pentaethylene glycol ditosylate in CH3CN in the presence of Cs2CO3. The corresponding cone conformer of the diisopropyl derivative (6) was synthesized via selective demethylation of the 1,3-dimethoxycalix-crown (2a) and subsequent dialkylation. Extraction experiments with alkali picrates reveal a strong preference of ligands 4 for Cs+. Thermodynamic parameters obtained for the complexation of 4a show that the high stability constant in MeOH (log beta = 6.4 +/- 0.4) is reflected mainly in the large -Delta H-c value of 50.2 +/- 0.2 kJ . mol(-1). The entropy of complexation (T Delta S-c = -15 kJ . mol(-1)), less negative than for other crown ethers, is explained in terms of preorganization of 4a. The X-ray structure of the cesium picrate . 4a complex shows clearly that the cation is positioned between the two aromatic rings with short Cs-C distances of 3.49 and 3.69 Angstrom, respectively. H-1 MMR spectroscopy confirms this type of structure in solution. Ligands 4 incorporated in supported liquid membranes transport Cs+ cations with a high preference over Na+. By the application of an anion gradient, traces of Cs+ can be removed (greater than or equal to 99.8%) from acidic solutions (pH = 0) that contain 4 M of NaNO3.