2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethyl 2-((methyl-(pyridin-4-yl)carbamothioyl)thio)propanoate | 1326717-35-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethyl 2-((methyl-(pyridin-4-yl)carbamothioyl)thio)propanoate
• CAS: 1326717-35-4
• 化学式: C₁₈H₂₈N₂O₆S₂
• 分子量: 432.562
• InChiKey: LHFQEBVRNLKGOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.51
• 重原子数：
  28.0
• 可旋转键数：
  14.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  90.35
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethyl 2-((methyl-(pyridin-4-yl)carbamothioyl)thio)propanoate 、 对甲苯磺酸 以 氘代二甲亚砜 、 水 为溶剂， 生成 2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethyl 2-((methyl(pyridin-4-yl)carbamothioyl)thio)propanoate 4-methylbenzenesulfonate
  参考文献：
  名称：

  Switchable Reversible Addition–Fragmentation Chain Transfer (RAFT) Polymerization in Aqueous Solution,N,N-Dimethylacrylamide

  摘要：

  Reversible addition-fragmentation chain transfer (RAFT) polymerization of a "more activated monomer" (MAM), N,N-dimethylacrylamide (DMAm), has been successfully achieved in aqueous solution using an acid/base switchable pyridyl-substituted dithiocarbamate RAFT agent. The effect of strength (pK(a)) and stoichiometry of the acid used to switch the RAFT agent on the molecular weight and dispersity of poly(N,N-dimethylacrylamide) (PDMAm) were examined, making use of high-throughput protocol. Best control was achieved with a stoichiometric amount of the strongest acid investigated, p-toluenesulfonic acid monohydrate. Use of weaker acids (higher pK(a)) or less than stoichiometric amounts of acid with respect to RAFT agent resulted in broader molecular weight distributions. These results can be rationalized in terms of the extent of protonation of the pyridine nitrogen of the RAFT agent (pK(a) similar to 3.13). The preparation of unimodal low dispersity block copolymers of PDMAm with the "less-activated" monomers (LAMs) N-vinylcarbazole (NVC), vinyl acetate (VAc), and N-vinylpyrrolidone (NVP) demonstrated the fidelity of the RAFT end group in these experiments and provides a further example of the utility of switchable RAFT polymerization.

  DOI：

  10.1021/ma200760q
• 作为产物：
  描述：

  三缩四乙二醇 在 吡啶 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 7.0h， 生成 2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethyl 2-((methyl-(pyridin-4-yl)carbamothioyl)thio)propanoate
  参考文献：
  名称：

  Switchable Reversible Addition–Fragmentation Chain Transfer (RAFT) Polymerization in Aqueous Solution,N,N-Dimethylacrylamide

  摘要：

  Reversible addition-fragmentation chain transfer (RAFT) polymerization of a "more activated monomer" (MAM), N,N-dimethylacrylamide (DMAm), has been successfully achieved in aqueous solution using an acid/base switchable pyridyl-substituted dithiocarbamate RAFT agent. The effect of strength (pK(a)) and stoichiometry of the acid used to switch the RAFT agent on the molecular weight and dispersity of poly(N,N-dimethylacrylamide) (PDMAm) were examined, making use of high-throughput protocol. Best control was achieved with a stoichiometric amount of the strongest acid investigated, p-toluenesulfonic acid monohydrate. Use of weaker acids (higher pK(a)) or less than stoichiometric amounts of acid with respect to RAFT agent resulted in broader molecular weight distributions. These results can be rationalized in terms of the extent of protonation of the pyridine nitrogen of the RAFT agent (pK(a) similar to 3.13). The preparation of unimodal low dispersity block copolymers of PDMAm with the "less-activated" monomers (LAMs) N-vinylcarbazole (NVC), vinyl acetate (VAc), and N-vinylpyrrolidone (NVP) demonstrated the fidelity of the RAFT end group in these experiments and provides a further example of the utility of switchable RAFT polymerization.

  DOI：

  10.1021/ma200760q