1-Oxacyclotetradeca-7,9-diyn-2-one | 1346556-88-4

• 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: 1-Oxacyclotetradeca-7,9-diyn-2-one
• 英文别名: 1-oxacyclotetradeca-7,9-diyn-2-one
• CAS: 1346556-88-4
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: NQAPQTVBGZUKAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  hex-5-yn-1-yl hept-6-ynoate 在 吡啶 、 氧气 、 三乙胺 、 nickel(II) nitrate 、 copper dichloride 作用下， 以 甲醇 为溶剂， 以62%的产率得到1-Oxacyclotetradeca-7,9-diyn-2-one
  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

• Phase Separation As a Strategy Toward Controlling Dilution Effects in Macrocyclic Glaser-Hay Couplings
  作者：Anne-Catherine Bédard、Shawn K. Collins

  DOI：10.1021/ja208902t

  日期：2011.12.14

  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.