2-Oxo-oxacyclotricosadiin-(11.13) | 10458-34-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: 2-Oxo-oxacyclotricosadiin-(11.13)
• CAS: 10458-34-1
• 化学式: C₂₂H₃₄O₂
• 分子量: 330.511
• InChiKey: DAYIZIITWUWZHH-UHFFFAOYSA-N

物化性质

• 沸点：
  519.5±29.0 °C(predicted)
• 密度：
  0.96±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.79
• 重原子数：
  24.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  10-十一碳炔酸 在 吡啶 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 氧气 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 nickel(II) nitrate 、 copper dichloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 30.0h， 生成 2-Oxo-oxacyclotricosadiin-(11.13)
  参考文献：
  名称：

  Phase Separation As a Strategy Toward Controlling Dilution Effects in Macrocyclic Glaser-Hay Couplings

  摘要：

  Macrocycles are abundant in numerous chemical applications, however the traditional strategy for the preparation of these compounds remains cumbersome and environmentally damaging; involving tedious reaction set-ups and extremely dilute reaction media. The development of a macrocyclization strategy conducted at high concentrations is described which exploits phase separation of the catalyst and substrate, as a strategy to control dilution effects. Sequestering a copper catalyst in a highly polar and/or hydrophilic phase can be achieved using a hydrophilic ligand, T-PEG(1900), a PEGylated TMEDA derivative. Similarly, phase separation is possible when suitable copper complexes are soluble in PEG(400), a green and efficient solvent which can be utilized in biphasic mixtures for promoting macrocyclization at high concentrations. The latter phase separation technique can be exploited for the synthesis of a wide range of industrially relevant macrocycles with varying ring sizes and functional groups.

  DOI：

  10.1021/ja208902t

文献信息

• Microwave accelerated Glaser–Hay macrocyclizations at high concentrations
  作者：Anne-Catherine Bédard、Shawn K. Collins

  DOI：10.1039/c2cc32464d

  日期：——

  Efficient macrocyclization can be conducted at high concentrations employing microwave irradiation and a phase separation strategy. The rate of the Glaser–Hay macrocyclization is accelerated using microwave irradiation and reaction times decreased from 48 h to 1–6 h, depending on the nature of the substrate. Macrocyclization concentrations could be increased up to 0.1 M compared to traditional concentrations (0.2 mM).

  可以利用微波照射和相分离策略，在高浓度下进行有效的环化反应。通过微波照射，Glaser-Hay环化反应的速率加快，反应时间从48小时缩短到1至6小时，具体取决于底物的性质。与传统浓度（0.2 mM）相比，环化反应的浓度可以提高到0.1 M。