4-vinylbenzyl 4-imidazolecarboxylate | 855596-28-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-vinylbenzyl 4-imidazolecarboxylate
• 英文别名: (4-ethenylphenyl)methyl 1H-imidazole-5-carboxylate
• CAS: 855596-28-0
• 化学式: C₁₃H₁₂N₂O₂
• 分子量: 228.25
• InChiKey: CXJOFOHKUWCHBE-UHFFFAOYSA-N

物化性质

• 沸点：
  455.5±25.0 °C(Predicted)
• 密度：
  1.230±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-氯甲基苯乙烯 、 1H-咪唑-4-甲酸 在 caesium carbonate 、 三乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以10.3%的产率得到4-vinylbenzyl 4-imidazolecarboxylate
  参考文献：
  名称：

  Highly Branched Poly(N-isopropylacrylamide)s with Imidazole End Groups Prepared by Radical Polymerization in the Presence of a Styryl Monomer Containing a Dithioester Group

  摘要：

  Highly branched poly(N-isopropylacrylamide) (PNIPAM) compounds were prepared by copolymerization of 3H-imidazole-4-carbodithioic acid 4-vinylbenzyl ester, 1, with N-isopropylacrylamide (NIPAM) using reversible addition-fragmentation chain transfer (RAFT) polymerization. The polymerizations proceeded well with few side reactions. An increase in the content of 1 in the monomer feed appears to increase the number of branch chains, and at the same time no evidence was obtained for the presence of substituted acrylamide chain ends that may potentially result via elimination of the dithioate group. The polymer products show a clear tendency to increased molecular weight as the extent of conversion of monomer increases, while size exclusion chromatography (SEC) profiles indicate a complex distribution of molecular weights compared to linear polymers obtained with a non-RAFT carboxylate monomer. Both NMR and viscometry indicate that, as expected, increasing the amount of I in the feed has the effect of increasing the degree of branching in the final product. This increase in branching reduces the intrinsic viscosity of the solutions of the highly branched polymers compared to similar linear polymers. Poly(N-isopropylacrylamide) displays a lower critical solution temperature (LCST) in aqueous solutions, and cloud point data indicate a clear effect of chain architecture on the temperature at which this transition occurs. Thus, a set of linear analogous copolymers have LCST's that, for equivalent mole fractions of imidazole content, are higher than the similar highly branched polymers. However, on complexation of copper by the imidazole groups the LCSTs of the linear and highly branched sets cannot be differentiated.

  DOI：

  10.1021/ma047742n

文献信息

• Highly Branched Poly(<i>N</i>-isopropylacrylamide)s with Imidazole End Groups Prepared by Radical Polymerization in the Presence of a Styryl Monomer Containing a Dithioester Group
  作者：Steven Carter、Barry Hunt、Stephen Rimmer

  DOI：10.1021/ma047742n

  日期：2005.5.1

  Highly branched poly(N-isopropylacrylamide) (PNIPAM) compounds were prepared by copolymerization of 3H-imidazole-4-carbodithioic acid 4-vinylbenzyl ester, 1, with N-isopropylacrylamide (NIPAM) using reversible addition-fragmentation chain transfer (RAFT) polymerization. The polymerizations proceeded well with few side reactions. An increase in the content of 1 in the monomer feed appears to increase the number of branch chains, and at the same time no evidence was obtained for the presence of substituted acrylamide chain ends that may potentially result via elimination of the dithioate group. The polymer products show a clear tendency to increased molecular weight as the extent of conversion of monomer increases, while size exclusion chromatography (SEC) profiles indicate a complex distribution of molecular weights compared to linear polymers obtained with a non-RAFT carboxylate monomer. Both NMR and viscometry indicate that, as expected, increasing the amount of I in the feed has the effect of increasing the degree of branching in the final product. This increase in branching reduces the intrinsic viscosity of the solutions of the highly branched polymers compared to similar linear polymers. Poly(N-isopropylacrylamide) displays a lower critical solution temperature (LCST) in aqueous solutions, and cloud point data indicate a clear effect of chain architecture on the temperature at which this transition occurs. Thus, a set of linear analogous copolymers have LCST's that, for equivalent mole fractions of imidazole content, are higher than the similar highly branched polymers. However, on complexation of copper by the imidazole groups the LCSTs of the linear and highly branched sets cannot be differentiated.