benzyl N-[4-oxo-4-[4-(3-oxo-2,4,5-triphenylcyclopenta-1,4-dien-1-yl)anilino]butyl]carbamate | 808766-50-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: benzyl N-[4-oxo-4-[4-(3-oxo-2,4,5-triphenylcyclopenta-1,4-dien-1-yl)anilino]butyl]carbamate
• CAS: 808766-50-9
• 化学式: C₄₁H₃₄N₂O₄
• 分子量: 618.732
• InChiKey: DDUCJQHSUOCPOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.44
• 重原子数：
  47.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  84.5
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  四(4-乙炔基苯)甲烷 、 benzyl N-[4-oxo-4-[4-(3-oxo-2,4,5-triphenylcyclopenta-1,4-dien-1-yl)anilino]butyl]carbamate 以 邻二甲苯 为溶剂， 生成 benzyl N-[4-oxo-4-[4-[2,3,6-triphenyl-4-[4-[tris(4-ethynylphenyl)methyl]phenyl]phenyl]anilino]butyl]carbamate 、 benzyl N-[4-oxo-4-[4-[2,3,6-triphenyl-5-[4-[tris(4-ethynylphenyl)methyl]phenyl]phenyl]anilino]butyl]carbamate
  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：

  N-苄氧羰基-4-氨基丁酸 、 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73%的产率得到benzyl N-[4-oxo-4-[4-(3-oxo-2,4,5-triphenylcyclopenta-1,4-dien-1-yl)anilino]butyl]carbamate
  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