1,6-bis(2-ethynylphenoxy)hexane | 96172-85-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,6-bis(2-ethynylphenoxy)hexane
• 英文别名: 1,6-Bis-(2-ethinyl-phenoxy)-hexan
• CAS: 96172-85-9
• 化学式: C₂₂H₂₂O₂
• 分子量: 318.415
• InChiKey: IXEDTZVGYKIYSS-UHFFFAOYSA-N

物化性质

• 沸点：
  476.1±40.0 °C(predicted)
• 密度：
  1.08±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.67
• 重原子数：
  24.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1,6-bis(2-ethynylphenoxy)hexane 在 吡啶 、 氧气 、 三乙胺 、 nickel(II) nitrate 、 copper dichloride 作用下， 以 甲醇 为溶剂， 以98%的产率得到2,2'--diphenyldiacetylen
  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
• 作为产物：
  描述：

  2-碘苯酚 在 正丁基锂 、 四甲基乙二胺 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 20.17h， 生成 1,6-bis(2-ethynylphenoxy)hexane
  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

• Cyclic Acetylenes. V. Syntheses and Properties of Strained Cyclic Ethers of<i>o</i>,<i>o</i>′-Dihydroxydiphenyldiacetylene
  作者：Fumio Toda、Masazumi Nakagawa

  DOI：10.1246/bcsj.34.862

  日期：1961.6