2-[2-(1-chloroethoxy)ethoxy]benzyl 2-chloro-2-phenylacetate | 1175537-82-2

• 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: 2-[2-(1-chloroethoxy)ethoxy]benzyl 2-chloro-2-phenylacetate
• 英文别名: [2-[2-(1-Chloroethoxy)ethoxy]phenyl]methyl 2-chloro-2-phenylacetate；[2-[2-(1-chloroethoxy)ethoxy]phenyl]methyl 2-chloro-2-phenylacetate
• CAS: 1175537-82-2
• 化学式: C₁₉H₂₀Cl₂O₄
• 分子量: 383.271
• InChiKey: DBJNGNWCGPZHQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[2-(1-chloroethoxy)ethoxy]benzyl 2-chloro-2-phenylacetate 、 2-羟甲基-15-冠-5 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以57%的产率得到[2-[2-[1-(1,4,7,10,13-Pentaoxacyclopentadec-2-ylmethoxy)ethoxy]ethoxy]phenyl]methyl 2-chloro-2-phenylacetate
  参考文献：
  名称：

  Template-Assisted Selective Radical Addition toward Sequence-Regulated Polymerization: Lariat Capture of Target Monomer by Template Initiator

  摘要：

  Surprisingly high monomer selectivity was demonstrated in competitive radical addition with two kinds of methacrylates carrying sodium and ammonium cation. Crucial is size-specific recognition by a lariat crown ether embedded close to the reactive halide in a designer template initiator. Especially, a combination with an active ruthenium catalyst led to outstanding selectivity at low temperature. This template system will open the way to unprecedented sequence-regulated polymerization.

  DOI：

  10.1021/ja1070575
• 作为产物：
  描述：

  2-[2-(vinyloxy)ethoxy]benzyl 2-chloro-2-phenylacetate 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 生成 2-[2-(1-chloroethoxy)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

文献信息

• Selective Radical Addition with a Designed Heterobifunctional Halide: A Primary Study toward Sequence-Controlled Polymerization upon Template Effect
  作者：Shohei Ida、Takaya Terashima、Makoto Ouchi、Mitsuo Sawamoto

  DOI：10.1021/ja9031314

  日期：2009.8.12

  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.
• Template-Assisted Selective Radical Addition toward Sequence-Regulated Polymerization: Lariat Capture of Target Monomer by Template Initiator
  作者：Shohei Ida、Makoto Ouchi、Mitsuo Sawamoto

  DOI：10.1021/ja1070575

  日期：2010.10.27

  Surprisingly high monomer selectivity was demonstrated in competitive radical addition with two kinds of methacrylates carrying sodium and ammonium cation. Crucial is size-specific recognition by a lariat crown ether embedded close to the reactive halide in a designer template initiator. Especially, a combination with an active ruthenium catalyst led to outstanding selectivity at low temperature. This template system will open the way to unprecedented sequence-regulated polymerization.