tetra(ethylene glycol) benzyl vinyl ether | 253871-03-3

• 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: tetra(ethylene glycol) benzyl vinyl ether
• 英文别名: tetraethylene glycol benzyl vinyl ether；2,5,8,11,14-Pentaoxahexadec-15-ene, 1-phenyl-；2-[2-[2-(2-ethenoxyethoxy)ethoxy]ethoxy]ethoxymethylbenzene
• CAS: 253871-03-3
• 化学式: C₁₇H₂₆O₅
• 分子量: 310.39
• InChiKey: DAZPJTGWYZHUDV-UHFFFAOYSA-N

物化性质

• 沸点：
  398.2±37.0 °C(Predicted)
• 密度：
  1.042±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  22
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  15-冠醚-5 在 氢化钾 作用下， 以 四氢呋喃 为溶剂， 反应 0.42h， 生成 tetra(ethylene glycol) benzyl vinyl ether
  参考文献：
  名称：

  Electron-transfer reduction of selected alcohols with alkalide K−, K+(15-crown-5)2 via organometallic intermediates

  摘要：

  The course of the reaction of alkalide K-, K+(15-crown-5)(2) 1 with selected alcohols depends on the kind of alcohol and the mode of substrate delivery. In the case of methanol, potassium methoxide formed initially undergoes destruction at the excess of 1. It results in potassium oxide and methylpotassium. The latter opens the crown ether ring giving potassium tetraethylene glycoxide vinyl ether and methane. A similar course of the process is observed for propanol. Potassium glycidoxide is the main product formed in the reaction of 1 with glycidol. Its oxirane ring is opened at the excess of 1. Organopotassium alkoxides, i.e., potassium potassiomethoxide and dipotassium potassiopropane-1,2-dioxide are intermediate products of this reaction. They react then with the crown ether. Potassium methoxide, potassium enolate of acetaldehyde, dipotassium, propane-1,2-dioxide and potassium tetraethylene glycoxide vinyl ether are the final products of this process. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2004.04.026

文献信息

• Cleavage of different ether bonds in butyl glycidyl ether and allyl glycidyl ether by K−, K+(15-crown-5)2
  作者：Zbigniew Grobelny、Andrzej Stolarzewicz、Adalbert Maercker、Stanisław Krompiec、Tadeusz Bieg

  DOI：10.1016/s0022-328x(02)01801-6

  日期：2002.10

  alkyl glycidyl ethers affects the course of their reaction with K−, K+(15-crown-5)2. The cyclic oxirane ring is exclusively cleaved in the case of butyl glycidyl ether whereas the presence of the unsaturated allyl group in the glycidyl ether molecule unexpectedly prefers the scission of the linear ether bond. In both the systems organometallic intermediates are formed. They react with crown ether causing

  该种取代基在烷基缩水甘油醚影响它们具有K个反应过程中-，K +（15-冠-5）2。在丁基缩水甘油醚的情况下，环状环氧乙烷环仅被裂解，而在缩水甘油醚分子中不饱和烯丙基的存在出乎意料地倾向于裂解线性醚键。在这两个系统中均形成有机金属中间体。它们与冠醚反应，导致其开环。由烯丙基缩水甘油醚形成的烯丙基钾也与另一个缩水甘油醚分子反应；在这种情况下，环氧乙烷环是打开的。
• Decomposition of vinyl ethers by alkalide K−, K+(15-crown-5)2 via organopotassium intermediates
  作者：Zbigniew Grobelny、Andrzej Stolarzewicz、Adalbert Maercker、Stanisław Krompiec、Janusz Kasperczyk、Józef Rzepa

  DOI：10.1016/j.jorganchem.2004.02.004

  日期：2004.5

  The structure of vinyl ethers determines the direction of the C–O bond cleavage by alkalide K−, K+(15-crown-5)21. Highly reactive organopotassium compounds are intermediate products formed in the system containing phenyl vinyl ether, butyl vinyl ether, ethylene glycol butyl vinyl ether or triethylene glycol methyl vinyl ether. Vinylpotassium and butylpotassium react with 15-crown-5. The oxacyclic ring

  通过碱金属化合物ķO键裂解-乙烯基醚的结构决定了C的方向-，K +（15-冠-5）2 1。高反应性有机钾化合物是在系统中形成的中间产物，其包含苯基乙烯基醚，丁基乙烯基醚，乙二醇丁基乙烯基醚或三乙二醇甲基乙烯基醚。乙烯基钾和丁基钾与15冠-5反应。在这种情况下，后者的氧杂环开环。具有CH 2 CH 2 O单元的有机钾醚可消除乙烯。生成各种醇钾。反应1 与目前为止使用的其他乙烯基醚和大多数其他试剂相比，丁基乙烯基醚的反应非常缓慢。
• New facts concerning the reaction of K−, K+(15-crown-5)2 with phenyl glycidyl ether: unexpected formation of potassium cyclopropoxide
  作者：Zbigniew Grobelny、Andrzej Stolarzewicz、Adalbert Maercker、Wolfgang Demuth

  DOI：10.1016/s0022-328x(99)00444-1

  日期：1999.11

  new mechanism of the reaction of K−, K+(15-crown-5)2 with phenyl glycidyl ether is presented. The linear ether bond is attacked only to a small extent, if at all. As the main reaction path the oxirane bond in the β-position is cleaved, followed by the γ-elimination of potassium phenoxide and the formation of potassium cyclopropoxide. Crown ether ring opening also occurs in reactions with organometallic

  K的反应的新机制-，K +（15-冠-5）2与苯基缩水甘油醚被呈现。线性醚键仅在很小的程度上受到侵蚀。作为主要反应途径，β-位的环氧乙烷键被裂解，然后γ-消除苯酚钾和形成环丙醇钾。冠醚开环也发生在与有机金属中间体的反应中。
• Decomposition of the crown ether ring in the reaction of K−, K+(15-crown-5)2 with oxetane
  作者：Zbigniew Grobelny、Andrzej Stolarzewicz、Adalbert Maercker

  DOI：10.1016/s0022-328x(00)00229-1

  日期：2000.6

  oxacyclic rings occurs in the reaction of K−, K+(15-crown-5)2 with oxetane in tetrahydrofuran solution. Oxetane ring opening leads to the formation of organometallic compounds, which react with the crown molecule. Potassium methoxide, potassium n-propoxide as well as potassium tetra(ethylene glycoxide) vinyl ether are the main reaction products. It means that crown ether can act both as an activator and as

  两个氧杂环环的裂解在K的反应发生-，K +（15-冠-5）2用在四氢呋喃溶液中的氧杂环丁烷。氧杂环丁烷开环导致形成有机金属化合物，该有机金属化合物与冠状分子反应。甲醇钾，正丙醇钾以及四（乙二醇乙二醇）乙烯基醚钾是主要反应产物。这意味着冠醚在研究条件下既可以起到活化剂的作用，也可以起到试剂的作用。
• New concept for the preparation of potassium sodides: the use of hexane as a non-polar solvent
  作者：Zbigniew Grobelny、Andrzej Stolarzewicz、Barbara Morejko-Buż、Antoni Winiarski

  DOI：10.1016/s0040-4020(03)00185-6

  日期：2003.3

  contact with 15-crown-5 hexane solution became potassium sodide K+(15-crown-5)2Na−. After the evaporation of hexane the crystalline solid product was analyzed by X-ray diffraction and the lattice parameters were calculated. The potassium sodide thus obtained could be easily dissolved in tetrahydrofuran. A deep blue solution containing sodium anions and complexed potassium cations was formed with a very

  与15-冠-5己烷溶液接触的NaK合金成为钾sodideķ +（15-冠-5）2的Na - 。蒸发己烷后，通过X射线衍射分析结晶固体产物，并计算晶格参数。由此获得的钠化钾可以容易地溶解在四氢呋喃中。形成了含有钠阴离子和复合钾阳离子的深蓝色溶液，其溶剂化电子的浓度非常低，即约为10 -7M  。在这种情况下，未检测到钾离子。一种新的结晶钾sodideķ +（DCH-24-冠8）2的Na - 用NaK合金和二环己基-24-冠-8己烷溶液制得。