phenyl 4-amino-2-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)benzoate | 1447497-25-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: phenyl 4-amino-2-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)benzoate
• 英文别名: Phenyl 4-amino-2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]benzoate
• CAS: 1447497-25-7
• 化学式: C₂₀H₂₅NO₆
• 分子量: 375.422
• InChiKey: CAXZUXMCXJBJPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  27
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  89.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  phenyl 4-amino-2-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)benzoate 、 4-甲氧基苯甲醛 在 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 以53%的产率得到phenyl 4-((4-methoxybenzyl)amino)-2-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)benzoate
  参考文献：
  名称：

  Bis-TEGylated Poly(p-benzamide)s: Combining Organosolubility with Shape Persistence

  摘要：

  The synthesis of perfectly planar, bis-substituted aromatic polyamides is reported herein. With highly flexible triethylene glycol chains attached and conformational restriction through intramolecular, bifurcated hydrogen bonds these are among the most shape-persistent yet organo-soluble polymers to date. Starting from 4-nitrosalicylic acid, our group developed a route to phenyl-2,5-bis-TEGylated aminobenzoate, which could be polymerized by addition of lithium bis(trimethylsilyl)amide (LiHMDS). Since this technique has not been applied to step-growth polycondensations of polyaramides so far, the influence of two different solvents and an N-protective group was investigated. Therefore, substituted phenyl aminobenzoate derivatives carrying a free amine or an N-protective group have been polymerized. Additionally, the tendency for self-assembly of the readily soluble bis-TEGylated poly(p-benzamide) was observed by transmission electron microscopy (TEM) in the dried state. Dynamic light scattering (DLS) measurements of chloroform solutions did not indicate the formation of aggregates. Thus, intermolecular interactions, which other aromatic polyamides typically exhibit, are prevented. The access to bis-substituted, entirely rigid poly(p-benzamide)s via this new polycondensation method paves the way for exciting new structures in materials science and supramolecular chemistry.

  DOI：

  10.1021/ma4010023
• 作为产物：
  描述：

  phenyl 2-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-4-nitrobenzoate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 40.0 ℃ 、4.0 MPa 条件下， 反应 40.0h， 以97%的产率得到phenyl 4-amino-2-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)benzoate
  参考文献：
  名称：

  Bis-TEGylated Poly(p-benzamide)s: Combining Organosolubility with Shape Persistence

  摘要：

  The synthesis of perfectly planar, bis-substituted aromatic polyamides is reported herein. With highly flexible triethylene glycol chains attached and conformational restriction through intramolecular, bifurcated hydrogen bonds these are among the most shape-persistent yet organo-soluble polymers to date. Starting from 4-nitrosalicylic acid, our group developed a route to phenyl-2,5-bis-TEGylated aminobenzoate, which could be polymerized by addition of lithium bis(trimethylsilyl)amide (LiHMDS). Since this technique has not been applied to step-growth polycondensations of polyaramides so far, the influence of two different solvents and an N-protective group was investigated. Therefore, substituted phenyl aminobenzoate derivatives carrying a free amine or an N-protective group have been polymerized. Additionally, the tendency for self-assembly of the readily soluble bis-TEGylated poly(p-benzamide) was observed by transmission electron microscopy (TEM) in the dried state. Dynamic light scattering (DLS) measurements of chloroform solutions did not indicate the formation of aggregates. Thus, intermolecular interactions, which other aromatic polyamides typically exhibit, are prevented. The access to bis-substituted, entirely rigid poly(p-benzamide)s via this new polycondensation method paves the way for exciting new structures in materials science and supramolecular chemistry.

  DOI：

  10.1021/ma4010023