1-O-ethyl 4-O-[2-[2-(2-iodoethoxy)ethoxy]ethyl] (E)-but-2-enedioate | 188915-82-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1-O-ethyl 4-O-[2-[2-(2-iodoethoxy)ethoxy]ethyl] (E)-but-2-enedioate
• CAS: 188915-82-4
• 化学式: C₁₂H₁₉IO₆
• 分子量: 386.184
• InChiKey: RKIRSLINJTWQAT-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-O-ethyl 4-O-[2-[2-(2-iodoethoxy)ethoxy]ethyl] (E)-but-2-enedioate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 2.0h， 以37%的产率得到11-ethoxycarbonyl-2,5,8-trioxa-1-oxocyclododecane
  参考文献：
  名称：

  Formation of substituted macrocyclic ethers by radical cyclisation

  摘要：

  ω-碘聚氧乙烯醚丙烯酸酯及相关化合物经三丁基锡烷处理后会发生自由基环化反应，生成取代的大环聚醚。

  DOI：

  10.1039/a608494j
• 作为产物：
  描述：

  1-O-ethyl 4-O-[2-[2-(2-hydroxyethoxy)ethoxy]ethyl] (E)-but-2-enedioate 在 吡啶 、 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 18.0h， 生成 1-O-ethyl 4-O-[2-[2-(2-iodoethoxy)ethoxy]ethyl] (E)-but-2-enedioate
  参考文献：
  名称：

  Macrocyclic Ethers by Free Radical Cyclizations

  摘要：

  Tin hydride reduction of omega-iodo-polyoxaalkyl acrylates 1 using syringe pump addition of both reactants to a solution of AIBN in benzene at 80 degrees C afforded the corresponding cyclic polyethers in excellent yields.

  DOI：

  10.1080/00397919708004135

文献信息

• Structural and conformational study of macrocyclic polyethers by NMR spectroscopy and molecular modeling
  作者：A. Philippon、M. Laguerre、M. Petraud、I. Pianet

  DOI：10.1002/(sici)1097-458x(199711)35:10<691::aid-omr155>3.0.co;2-6

  日期：1997.11

  Two macrocyclic polyether isomers were obtained by radical cyclization of (E)-8-iodo-3,6-dioxaoctyl-3-ethoxycarbonylpropenoate and separated by liquid-solid chromatography over silica gel. They were characterized, for the first time, by two-dimensional NMR; notably, the HMBC experiment gave access to the assignment of the two isomers through coupling via the carbonyl oxygen belonging to the macroheterocycle. The determination of the (3)J(HH) coupling, associated with Monte Carlo simulation, gave information on the conformational space of these two isomers and showed that 85 conformers for one isomer and 29 conformers for the other were in equilibrium in the solution mixture. These results are discussed with regard to the complexing properties of these macrocyclic polyethers. (C) 1997 John Wiley & Sons, Ltd.