1,1'-[ethane-1,2-diylbis(oxyethane-2,1-diyloxy)]bis[4-(chloromethyl)benzene] | 197573-07-2

• 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: 1,1'-[ethane-1,2-diylbis(oxyethane-2,1-diyloxy)]bis[4-(chloromethyl)benzene]
• 英文别名: 1,10-bis[4-(chloromethyl)phenyl]-1,4,7,10-tetraoxadecane；Triethylene glycol di-p-chlorobenzyl ether
• CAS: 197573-07-2
• 化学式: C₂₀H₂₄Cl₂O₄
• 分子量: 399.314
• InChiKey: MIDHGMZQQLGZEO-UHFFFAOYSA-N

物化性质

• 熔点：
  76-77 °C
• 沸点：
  533.5±50.0 °C(Predicted)
• 密度：
  1.201±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.66
• 重原子数：
  26.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1,1'-[ethane-1,2-diylbis(oxyethane-2,1-diyloxy)]bis[4-(chloromethyl)benzene] 在 二异丁基氢化铝 、 sodium carbonate 作用下， 以 乙腈 为溶剂， 生成 7,10,13,16-tetraoxa-1,22,25,30-tetraazatetracyclo[20.5.5.23,6.217,20]hexatriaconta-3,5,17,19,33,35-hexaene
  参考文献：
  名称：

  基于双臂和四臂循环的密码体

  摘要：

  摘要 制备了双臂和四臂环烯基穴状配体（1a-1d 和 2），它们通过二亚乙基氧基和三亚乙基氧基单元连接两个芳环。1:1 混合物 ([Ag+]/[配体]) 的 CSI-MS 表明这些新的穴状配体与 Ag+ 形成 1:1 复合物。Ag+ 和 2 之间相互作用的 log K 值大于 1a-1d、双臂循环 (3a-3c 和 4) 和四臂循环 (5) 的 log K 值。Ag+-离子诱导的 1H NMR 光谱变化表明，Ag+ 配合物与穴状配体（1a-1d 和 2）的 Ag+-π 相互作用强于 Ag+/双臂和四臂循环中的相互作用。为了可视化 Ag+-π 相互作用，在 B3LYP/3-21G(*) 理论水平计算了 Ag+ 复合物的 LUMO 和 HOMO 的等值面。Ag+ 离子的 LUMO 通过与芳香侧臂的 HOMO 相互作用而扭曲。计算揭示了 Ag+ 离子和芳香侧臂之间的 Ag+-π 相互作用，这些以图形方式显示。

  DOI：

  10.1080/10610278.2016.1239829
• 作为产物：
  描述：

  1,8-bis[4-(hydroxymethyl)phenoxy]-3,6-dioxaoctane 在 吡啶 、 氯化亚砜 作用下， 以 苯 为溶剂， 反应 2.0h， 以94%的产率得到1,1'-[ethane-1,2-diylbis(oxyethane-2,1-diyloxy)]bis[4-(chloromethyl)benzene]
  参考文献：
  名称：

  Gunter, Maxwell J.; Jeynes, Tyrone P.; Johnston, Martin R., Journal of the Chemical Society. Perkin transactions I, 1998, # 12, p. 1945 - 1957

  摘要：

  DOI：

文献信息

• Flexible Semicrown Ether‐Linked Symmetric Cationic Gemini Surfactants: Synthesis and Evaluation as Catalysts for Acceleration of Diastereoselective [3 + 2] Cycloaddition Reaction in Reversed Phase Micellar Media
  作者：Serkan Öztürk、Ayhan Yıldırım、Gökhan Gece、Haluk Türkdemir

  DOI：10.1002/jsde.12226

  日期：2019.3

  Novel cationic gemini surfactants with a hydrophilic oligo‐oxyethylene spacer group were synthesized and their physicochemical properties were identified. Computational studies for these compounds were also performed; molecular geometry, frontier molecular orbitals, and quantum chemical parameters were calculated using density functional theory (DFT). After exploration for catalytic activity, it was

  合成了具有亲水性低聚氧乙烯间隔基的新型阳离子双子表面活性剂，并鉴定了其理化性质。还对这些化合物进行了计算研究。使用密度泛函理论（DFT）计算了分子的几何形状，前沿的分子轨道和量子化学参数。在探索催化活性之后，发现这些表面活性剂可以有效地促进反相胶束介质中的[3 + 2]环加成反应。
• Synthesis and Surface Characterization Studies of Polyether-Linked Symmetric Higher Sulfanyl-1,3,4-Oxadiazoles
  作者：A. Yıldırım、S. Öztürk

  DOI：10.1080/10426507.2014.999067

  日期：2015.9.2

  The synthesis and the characterization of a series of novel symmetric double length alkyl-chained sulfanyl-1,3,4-oxadiazoles functionalized with a polyether head group are reported. In addition, surface characterization studies were conducted on the metal surface of these synthesized compounds. The metal surfaces were characterized by contact angle measurements via the sessile-drop method, and 3D images of the metal surface were obtained using an optical profilometer. The surface studies showed that the inhibitor molecule increases the hydrophobic character and decreases the wettability of the metal surface.
• Molecular Receptors for Adenine and Guanine Employing Metal Coordination, Hydrogen-Bonding and π-Stacking Interactions
  作者：James E. Kickham、Stephen J. Loeb、Shannon L. Murphy

  DOI：10.1002/chem.19970030807

  日期：1997.8

  AbstractThiacyclophane ligands 1 and 2, containing a meta‐xylyldithiaether unit, an aromatic spacing unit and a polyether chain, were prepared in good yield in a three‐step synthesis. The macrocyclic organopalladium complexes [Pd(L)‐(MeCN)][BF4] (3: L = 1; 4: L = 2) were prepared through palladation of the respective thiacyclophane ligand by reaction with [Pd(MeCN)4][BF4]2. These complexes act as metalloreceptors to aromatic amines such as p‐aminopyridine (pap), m‐aminopyridine (map) and the DNA nucleobases adenine and guanine. Binding occurs through simultaneous first‐ and second‐sphere coordination. This involves three separate interactions: first‐sphere σ donation from an aromatic N atom to the Pd centre, second‐sphere hydrogen bonds between the NH2 group and polyether O atoms, and π stacking between the electron‐poor aromatic rings of the substrate and the electron‐rich aromatic spacing units of the receptor. 1H NMR spectra exhibit chemical shift changes indicative of the H‐bonding and π‐stacking interactions in solution. X‐ray structures for thiacyclophane 1, metalloreceptor [Pd(1)(MeCN)][BF4] (3), metalloreceptor/model substrate complexes [Pd(1)(pap)][BF4 (5) and [Pd(2)‐(pap)][BF4] (7), and metalloreceptor/nucleobase complexes [Pd(1)(adenine)][BF4] (13), [Pd(2)(adenine)][BF4] (14) and [Pd(1)(guanine‐BF3)][BF4] (15b) show details of these interactions in the solid state.