(1,4,7,10,13,16-hexaoxacyclooctadecan-2-yl)methyl 4-methylbenzenesulfonate | 87708-33-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1,4,7,10,13,16-hexaoxacyclooctadecan-2-yl)methyl 4-methylbenzenesulfonate
• 英文别名: hydroxymethyl-18-crown-6 toluene-p-sulphonate；2-(p-Toluenesulfonyloxy)methyl-18-crown-6；Toluene-p-sulphonyloxymethyl-18-crown-6；tosylate of hydroxymethyl-18-crown-6；(tosyloxy)-methyl-18-crown-6；(tosyloxy)methyl-18-crown-6；1,4,7,10,13,16-Hexaoxacyclooctadec-2-ylmethyl 4-methylbenzenesulfonate
• CAS: 87708-33-6
• 化学式: C₂₀H₃₂O₉S
• 分子量: 448.535
• InChiKey: GVWVIAAEUSVEDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (1,4,7,10,13,16-hexaoxacyclooctadecan-2-yl)methyl 4-methylbenzenesulfonate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 生成 (1,4,7,10,13,16-六氧杂环十八烷-2-基)甲硫醇
  参考文献：
  名称：

  新型二茂铁冠醚的合成及络合性能

  摘要：

  合成了两种新型二茂铁冠化合物，其中二茂铁核带有一个和两个 18-crown-6 单元，并在溶剂萃取中检查了它们的碱金属阳离子络合。二茂铁双冠在竞争萃取中表现出对 K+ 和 Rb+ 的选择性。

  DOI：

  10.1246/cl.1984.37
• 作为产物：
  描述：

  2-羟甲基-18-冠-6 、 对甲苯磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以95%的产率得到(1,4,7,10,13,16-hexaoxacyclooctadecan-2-yl)methyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Recognition of Cations by Self-Assembled Monolayers of Crown Ethers

  摘要：

  Self-assembled monolayers (SAMs) of crown ether adsorbates on gold reversibly bind metal ions from aqueous solutions. The resulting changes of the electrochemical properties of the monolayers were monitored by impedance spectroscopy. The increased dielectric constant of the layer due to the complexation of ions results in an increase of the monolayer capacitance (C-ML). Analysis of the response curves with a Langmuir isotherm enables the determination of association constants of the SAMs with various metal ions. The cation binding also influences the charge-transfer resistance (R-CT) Of a redox couple Ru(NH3)(6)(2+/3+) in the electrolyte. Comparison of both responses allows an accurate interpretation of the origin of the resistive response. Furthermore, the association constants enable the quantitative determination of interactions between SAMs and metal ions, using either capacitive or resistive responses.

  DOI：

  10.1021/jp990014v

文献信息

• Enhancement of the rate of oxidative decarboxylation of pyruvic acid catalysed by crowned thiazolium in the presence of alkali metal cations in ethanol
  作者：Yumihiko Yano、Mikihiko Kimura、Kenji Shimaoka、Hideyuki Iwasaki

  DOI：10.1039/c39860000160

  日期：——

  Alkali metal cations (K+ and Na+) bound to 18-crown-6 having a pendant thiazolium ion were found to increase the rate of the oxidative decarboxylation of pyruvic acid in EtOH by binding the substrate and acting as the catalytic site.

  发现与具有噻唑侧离子侧基的18-冠-6结合的碱金属阳离子（K +和Na +）通过结合底物并充当催化位点来提高丙酮酸在EtOH中的氧化脱羧速率。
• SYNTHESIS AND COMPLEXING PROPERTIES OF NOVEL FERROCENE CROWN ETHERS
  作者：Bronislaw Czech、Anna Czech、Sang Ihn Kang、Richard A. Bartsch

  DOI：10.1246/cl.1984.37

  日期：1984.1.5

  Two novel ferrocene crown compounds in which the ferrocene nucleus bears one and two 18-crown-6 units are synthesized and their alkali metal cation complexation is examined in solvent extraction. The ferrocene biscrown exhibits selectivity for K+ and Rb+ in competitive extraction.

  合成了两种新型二茂铁冠化合物，其中二茂铁核带有一个和两个 18-crown-6 单元，并在溶剂萃取中检查了它们的碱金属阳离子络合。二茂铁双冠在竞争萃取中表现出对 K+ 和 Rb+ 的选择性。
• Molecular recognition of isomeric protonated amino acid esters monitored by ESI-mass spectrometry
  作者：Andrea Liesenfeld、Arne Lützen

  DOI：10.3762/bjoc.10.78

  日期：——

  Two new 9,9’-spirobifluorene-derived crown ethers were prepared and used to recognise constitutionally isomeric amino acid derivatives. The performance of the receptors was evaluated by ESI-mass spectrometry using the isomer labelled guest method (ILGM). This method revealed the preferred binding of L-norleucine and L-leucine compared to L-isoleucine for both receptors. Furthermore, non-covalent isotope effects demonstrate the relevance of dispersive interactions for the overall binding event. These effects also provide hints for the relative spatial orientation of the guest molecules within the host–guest complex, and thereby prove the importance of the spirobifluorene moiety for the observed binding of the protonated amino acid esters.

  制备了两种新的9,9'-螺二芴衍生的冠醚，并用于识别构成同分异构体的氨基酸衍生物。采用同位素标记的客体方法（ILGM）通过ESI-质谱法评价了受体的性能。该方法揭示了两种受体对L-诺亚鲁氨酸和L-亮氨酸的优先结合，相对于L-异亮氨酸。此外，非共价同位素效应证明了分散作用对于整体结合事件的相关性。这些效应还提供了有关客体分子在宿主-客体复合物中相对空间定向的提示，从而证明了螺二芴基团对质子化氨基酸酯的观察结合的重要性。
• Lipophilic crown phosphonic acid monoalkyl esters. Synthesis and solvent extraction
  作者：Jacek F. Koszuk、Bronislaw P. Czech、Wladyslaw Walkowiak、David A. Babb、Richard A. Bartsch

  DOI：10.1039/c39840001504

  日期：——

  Lipophilic crown phosphonic acid monoalkyl esters capable of anion-independent metal ion transport from acidic and neutral aqueous solutions into organic media have been synthesized and tested in competitive alkali metal solvent extraction.

  合成了亲脂性冠膦酸单烷基酯，该酯能够独立于阴离子将金属离子从酸性和中性水溶液转移到有机介质中，并已在竞争性碱金属溶剂萃取中进行了测试。
• Czech, Bronislaw P.; Desai, Dhimant H.; Koszuk, Jacek, Journal of Heterocyclic Chemistry, 1992, vol. 29, # 4, p. 867 - 875
  作者：Czech, Bronislaw P.、Desai, Dhimant H.、Koszuk, Jacek、Czech, Anna、Babb, David A.、at al.

  DOI：——

  日期：——