hex-5-yn-1-yl undec-10-ynoate | 1346556-99-7

• 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: hex-5-yn-1-yl undec-10-ynoate
• CAS: 1346556-99-7
• 化学式: C₁₇H₂₆O₂
• 分子量: 262.392
• InChiKey: XRRJHOMLULPXRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  19.0
• 可旋转键数：
  12.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  hex-5-yn-1-yl undec-10-ynoate 在 吡啶 、 氧气 、 三乙胺 、 nickel(II) nitrate 、 copper dichloride 作用下， 以 甲醇 为溶剂， 以74%的产率得到oxacyclooctadeca-11,13-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
• 作为产物：
  描述：

  5-己炔酸 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 30.0h， 生成 hex-5-yn-1-yl undec-10-ynoate
  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

• Influence of Poly(ethylene glycol) Structure in Catalytic Macrocyclization Reactions
  作者：Anne-Catherine Bédard、Shawn K. Collins

  DOI：10.1021/cs400050g

  日期：2013.4.5

  for conducting macrocyclizations using PEG/solvent mixtures, suggesting that macrocyclizations are most efficient at high ratios of PEG/MeOH and when employing medium-length lipophilic branched poly(propylene glycol) (PPG) polymers. In particular, the use of PPG bearing terminal uncapped hydroxyl groups allows for a significant reduction in the catalyst loading. The macrocyclization studies reinforce

  通过检查表面张力测量值和分离得到的H2O3化合物，对MeOH混合物中六种不同的聚乙二醇（PEG）衍生的聚合物在其聚集能力，控制稀释效果和催化作用方面的结构效应进行了首次评估。二炔3的Glaser-Hay模型环化反应模型。研究了三种不同的结构效应，其中包括：（1）聚合物末端羟基官能团上存在封端基团；（2）聚合物链的长度；（3）聚合物主链中支链烷基的作用。获得的数据为使用PEG /溶剂混合物进行大环化提供了重要的指导，表明在高比例的PEG / MeOH以及使用中等长度的亲脂性支化聚丙二醇（PPG）聚合物时，大环化是最有效的。特别地，使用带有末端未封端的PPG的PPG允许催化剂负载的显着降低。大环化研究强调，可以利用PEG衍生溶剂的聚集特性进行催化，