5-[4-(3-Oxo-2,4,5-triphenyl-cyclopenta-1,4-dienyl)-phenylcarbamoyl]-pentanoic acid methyl ester | 808766-54-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 5-[4-(3-Oxo-2,4,5-triphenyl-cyclopenta-1,4-dienyl)-phenylcarbamoyl]-pentanoic acid methyl ester
• 英文别名: methyl 6-oxo-6-[4-(3-oxo-2,4,5-triphenylcyclopenta-1,4-dien-1-yl)anilino]hexanoate
• CAS: 808766-54-3
• 化学式: C₃₆H₃₁NO₄
• 分子量: 541.646
• InChiKey: XPLNKIZJVVKMNO-UHFFFAOYSA-N

物化性质

• 沸点：
  786.7±60.0 °C(Predicted)
• 密度：
  1.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.46
• 重原子数：
  41.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  72.47
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  四苯基环戊二烯酮 、 四(4-乙炔基苯)甲烷 、 5-[4-(3-Oxo-2,4,5-triphenyl-cyclopenta-1,4-dienyl)-phenylcarbamoyl]-pentanoic acid methyl ester 以 邻二甲苯 为溶剂， 反应 42.0h， 生成 、 Methyl 6-oxo-6-[4-[2,3,6-triphenyl-4-[4-[tris[4-(2,3,4,5-tetraphenylphenyl)phenyl]methyl]phenyl]phenyl]anilino]hexanoate
  参考文献：
  名称：

  Toward Nanoamphiphiles:  Efficient Synthesis of Desymmetrized Polyphenylene Dendrimers

  摘要：

  A new synthetic approach for the desymmetrization of polyphenylene dendrimers (PPDs) is described. Tetrakis(4-ethynylphenyl)methane undergoes facile Diels-Alder cycloaddition with substoichiometric quantities of tetraphenylcyclopentadienones bearing one polar functional group. A single ethynyl group is thereby converted to a rigid, selectively functionalized polyphenylene moiety, which serves as a focal point for further transformations or interfacial anchoring. This is the key feature for the design of desymmetrized monodisperse macromolecules with a spherical shape. The remaining unreacted ethynyl groups provide a trifold core for the stepwise elaboration of first- and second-generation polyphenylene dendrons, which may, in turn, bear specific numbers of different peripheral functional groups at their terminae. Moreover, the resulting macromolecules exhibit the characteristic shape-persistence and monodispersity of PPDs. This approach is an important achievement in nanosciences, especially for tailoring new nanoamphiphiles. It is also of synthetic importance, as it enables the separation of two regioisomeric polyphenylene dendrimers for the first time.

  DOI：

  10.1021/jo048998u
• 作为产物：
  描述：

  脂肪酸甲酯 、 3-(4-Amino-phenyl)-2,4,5-triphenyl-cyclopenta-2,4-dienone 在 4-二甲氨基吡啶 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以85%的产率得到5-[4-(3-Oxo-2,4,5-triphenyl-cyclopenta-1,4-dienyl)-phenylcarbamoyl]-pentanoic acid methyl ester
  参考文献：
  名称：

  Toward Nanoamphiphiles:  Efficient Synthesis of Desymmetrized Polyphenylene Dendrimers

  摘要：

  A new synthetic approach for the desymmetrization of polyphenylene dendrimers (PPDs) is described. Tetrakis(4-ethynylphenyl)methane undergoes facile Diels-Alder cycloaddition with substoichiometric quantities of tetraphenylcyclopentadienones bearing one polar functional group. A single ethynyl group is thereby converted to a rigid, selectively functionalized polyphenylene moiety, which serves as a focal point for further transformations or interfacial anchoring. This is the key feature for the design of desymmetrized monodisperse macromolecules with a spherical shape. The remaining unreacted ethynyl groups provide a trifold core for the stepwise elaboration of first- and second-generation polyphenylene dendrons, which may, in turn, bear specific numbers of different peripheral functional groups at their terminae. Moreover, the resulting macromolecules exhibit the characteristic shape-persistence and monodispersity of PPDs. This approach is an important achievement in nanosciences, especially for tailoring new nanoamphiphiles. It is also of synthetic importance, as it enables the separation of two regioisomeric polyphenylene dendrimers for the first time.

  DOI：

  10.1021/jo048998u