[60]冠20 | 71092-63-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: [60]冠20
• 英文名称: <60>crown-20
• 英文别名: [60]-Crown-20；60-Crown-20；[60]crown-20；1,4,7,10,13,16,19,22,25,28,31,34,37,40,43,46,49,52,55,58-Icosaoxacyclohexacontane
• CAS: 71092-63-2
• 化学式: C₄₀H₈₀O₂₀
• 分子量: 881.063
• InChiKey: FAHPHQDBXJYJNC-UHFFFAOYSA-N

物化性质

• 沸点：
  931.0±60.0 °C(Predicted)
• 密度：
  0.995±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  60
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  185
• 氢给体数：
  0
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  [60]冠20 在 氦气 、 fluorine 、 sodium fluoride 作用下， 以 氯仿 、 1,1,2-三氯三氟乙烷（CFC-113） 为溶剂， 反应 72.0h， 以14%的产率得到Perfluoro[60]-crown-20
  参考文献：
  名称：

  最大的全氟大环化合物的合成；全氟 [60]-crown-20 和全氟 [30]-crown-10

  摘要：

  最大的全氟大环化合物全氟 [60]-crown-20 和全氟 [30]-crown-10 已使用新的连续添加溶液相直接氟化技术合成，并使用 19F NMR 和质谱法进行了表征。

  DOI：

  10.1039/b004168h
• 作为产物：
  描述：

  双[2-(2-氯化乙氧基)乙基]醚 在 四丁基硫酸氢铵 sodium hydroxide 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 生成 [60]冠20
  参考文献：
  名称：

  Synthesis and Characterization of Large (30-60-Membered) Aliphatic Crown Ethers

  摘要：

  We report a new synthetic approach to large. (30-72-membered) crown ethers based on isolation of the small and large Cyclic polyethers made by combination of 1 mol or 2 mol each, respectively, of oligo(ethylene glycol)s and oligo(ethylene glycol) ditosylates. The advantages of this approach are the use of readily available glycols Cup to hexa(ethylene glycol)l as starting materials and the ability to optimize the procedure for selective production of either macrocycle, producing yields superior or comparable to previous methods. At higher reaction temperatures the lai ge crown ether is preferentially formed. This approach has been used to produce the crown ethers on 100-g scales. Purification was achieved by a combination of filtration through silica gel, treatment with a polymeric acid chloride, and recrystallization techniques, avoiding standard column chromatography. The pure crown ethers, 60-crown-20, 48-crown-16, 42-crown-14, 36-crown-12, and 30-crown-10, were characterized by melting points, H-1- and C-13-NMR, elemental analysis, and/or MS, GC-MS, and TGA-MSI Melting points were as much as 26 degrees C higher than previously reported for these crown ethers. All the aliphatic crown ethers larger than 18-crown-6 decompose upon heating in air at ca. 200 degrees C.

  DOI：

  10.1021/jo00087a040

文献信息

• Template effects. 7. Large unsubstituted crown ethers from polyethylene glycols: Formation, analysis, and purification
  作者：Chiara Antonini Vitali、Bernardo Masci

  DOI：10.1016/s0040-4020(01)80080-6

  日期：1989.1

  tri- to deca-ethylene glycol yields not only the corresponding crown ethers but also higher cyclooligomers that can be analyzed up to about [60] crown-20 by glc: in particular [36] crown-12 and [48] crown-16 were obtained from tetraethylene glycol and purified by column chromatography on cellulose; iii) the reaction, as applied to commercial mixtures of polyethylene glycols (from PEG 200 to PEG 1000)

  通过聚乙二醇与甲苯磺酰氯和二恶烷中的异相 KOH 反应，不仅可以获得从 [12] 冠-4 到 [24] 冠-8 的冠状物，还可以获得一些较大的同系物。系统调查表明：i） [27] 冠-9 和 [30] 冠-10 可分别由壬醛和十醛乙二醇形成，并以纯形式分离;ii） 从三乙二醇到十乙二醇的整个聚乙二醇系列不仅产生相应的冠醚，还产生更高的环低聚物，这些低聚物可以通过 GLC 分析至约 [60] 冠-20：特别是 [36] 冠-12 和 [48] 冠-16 是从四乙二醇中获得的，并通过纤维素柱色谱纯化;iii） 该反应应用于聚乙二醇的商业混合物（从 PEG 200 到 PEG 1000）时，在大环尺寸区域也能得到相当高的冠醚产率。讨论了 K+ 离子的模板效应和环寡聚化反应对各种环尺寸的贡献。
• Synthesis of large ring crown ethers
  作者：Robert Chênevert、Linda D'Astous

  DOI：10.1002/jhet.5570230637

  日期：1986.11

  The synthesis of large ring crown compounds with the general structure 3n-crown-n where n is 9 to 20 is reported.

  据报道，合成大环冠化合物的一般结构为3n-crown-n，其中n为9至20。
• Gibson, Harry W.; Liu, Shu; Lecavalier, Pierre, Journal of the American Chemical Society, 1995, vol. 117, # 3, p. 852 - 872
  作者：Gibson, Harry W.、Liu, Shu、Lecavalier, Pierre、Wu, Charles、Shen, Ya Xi

  DOI：——

  日期：——
• Crystal structures of 30-crown-10 and its tetrahydrate
  作者：Mukesh C. Bheda、Joseph S. Merola、Wendy A. Woodward、Venkatesh J. Vasudevan、Harry W. Gibson

  DOI：10.1021/jo00086a017

  日期：1994.4

  Detailed characterization of 30-crown-10 (30C10) with NMR spectroscopy, TGA, DSC, and X-ray crystallography is reported. The anhydrous 30C10 crystal is orthorhombic, belonging to space group Pbca: a = 8.606(1) Angstrom, b = 8.260(1) Angstrom, and c = 33.310(4) Angstrom. The 30C10.4H(2)O crystal is monoclinic, belonging to the space group P2(1)/c and having unit-cell parameters of a = 8.332(4) Angstrom, b = 9.083(2) Angstrom, c = 18.665(5) Angstrom, and b = 90.24(3)degrees. The four water molecules located in the cavity are bound to each other and to the crown ether but not to water or crown ether molecules of neighboring units. The stacking of the 30C10 molecules forms channels through the crystal lattice. In 30C10.4H(2)O the water molecules occupy the channels formed by the stacking of the crown ether molecules. This study is the first X-ray diffraction study of a simple aliphatic crown ether larger than 18-crown-6 and also the first such study of a tetrahydrate complex of any crown ether in the absence of other guest species.
• Gibson Harry W., Bheda Mukesh C., Engen Paul, Shen Ya Xi, Sze Jean, Zhang+, J. Org. Chem, 59 (1994) N 8, S 2186-2196
  作者：Gibson Harry W., Bheda Mukesh C., Engen Paul, Shen Ya Xi, Sze Jean, Zhang+

  DOI：——

  日期：——