{2-[2-(vinyloxy)ethoxy]phenyl}methanol | 1175537-80-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: {2-[2-(vinyloxy)ethoxy]phenyl}methanol
• CAS: 1175537-80-0
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: SRFREJOHNMVYRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.72
• 重原子数：
  14.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  {2-[2-(vinyloxy)ethoxy]phenyl}methanol 、 DL-2-氯-2-苯基乙酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 以73%的产率得到2-[2-(vinyloxy)ethoxy]benzyl 2-chloro-2-phenylacetate
  参考文献：
  名称：

  Selective Radical Addition with a Designed Heterobifunctional Halide: A Primary Study toward Sequence-Controlled Polymerization upon Template Effect

  摘要：

  A ruthenium(II)-catalyzed, highly selective, quantitative radical addition of an alkene, methacrylic acid (MAA), has been achieved by using a template halide (2) containing a built-in amine group as a recognition site for the carboxyl group of the substrate. The specific ionic binding of MAA by the amine template (1:1 molar ratio) led to preferential formation of the 1:1 MAA-2 adduct, whereas a similar halide without a template induced MAA oligomerization even in the presence of an externally added amine. A competitive radical addition of MAA versus its ester form [methyl methacrylate (MMA)] on the halide further demonstrated that the substrate selectivity [k'(MAA)/k'(MMA)] for 2 is enhanced more than 10 times by the intramolecular introduction of the template relative to the result for the nontemplate halide. These specificities are most likely triggered by the specific interaction (recognition) of the carboxyl group in MAA via the acid-selective template amine, which is implanted in the close vicinity of the radical addition site in 2. These results intimate possibility of control over the repeat-unit sequence in precision polymerization.

  DOI：

  10.1021/ja9031314
• 作为产物：
  描述：

  水杨醇 、 2-氯乙基乙烯基醚 在 四丁基溴化铵 、 potassium hydroxide 作用下， 以 水 为溶剂， 反应 24.0h， 以68%的产率得到{2-[2-(vinyloxy)ethoxy]phenyl}methanol
  参考文献：
  名称：

  Selective Radical Addition with a Designed Heterobifunctional Halide: A Primary Study toward Sequence-Controlled Polymerization upon Template Effect

  摘要：

  A ruthenium(II)-catalyzed, highly selective, quantitative radical addition of an alkene, methacrylic acid (MAA), has been achieved by using a template halide (2) containing a built-in amine group as a recognition site for the carboxyl group of the substrate. The specific ionic binding of MAA by the amine template (1:1 molar ratio) led to preferential formation of the 1:1 MAA-2 adduct, whereas a similar halide without a template induced MAA oligomerization even in the presence of an externally added amine. A competitive radical addition of MAA versus its ester form [methyl methacrylate (MMA)] on the halide further demonstrated that the substrate selectivity [k'(MAA)/k'(MMA)] for 2 is enhanced more than 10 times by the intramolecular introduction of the template relative to the result for the nontemplate halide. These specificities are most likely triggered by the specific interaction (recognition) of the carboxyl group in MAA via the acid-selective template amine, which is implanted in the close vicinity of the radical addition site in 2. These results intimate possibility of control over the repeat-unit sequence in precision polymerization.

  DOI：

  10.1021/ja9031314