4-[3,5-bis(2-ethynyl)phenyl]-2-methyl-3-butyn-2-ol | 1417696-91-3

• 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: 4-[3,5-bis(2-ethynyl)phenyl]-2-methyl-3-butyn-2-ol
• CAS: 1417696-91-3
• 化学式: C₁₅H₁₂O
• 分子量: 208.26
• InChiKey: HONDCLMZMJZDHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.77
• 重原子数：
  16.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  4,4''-bis((4-(tert-butyl)benzyl)oxy)-5'-iodo-2'-(phenylethynyl)-1,1':3',1''-terphenyl 、 4-[3,5-bis(2-ethynyl)phenyl]-2-methyl-3-butyn-2-ol 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以75%的产率得到4-[3,5-Bis[2-[3,5-bis[4-[(4-tert-butylphenyl)methoxy]phenyl]-4-(2-phenylethynyl)phenyl]ethynyl]phenyl]-2-methylbut-3-yn-2-ol
  参考文献：
  名称：

  Construction of Snowflake-Shaped Dendritic Covalent Assemblies with Rigid Conjugated Networks

  摘要：

  A convergent method for the construction of shape-persistent nanoscale assemblies with conjugated backbones was developed. The copper-free Sonogashira coupling reaction was successfully applied to the formation of multiple covalent connections between conjugated terminals (iodide substituted aryl groups) of AB(2)-type outer components and four conjugated terminals (acetylenic bonds) of an inner A(4)-type core dendrimer. The conjugated networks in the starting components are expanded during the assembly process to afford nanoscale dendritic conjugated networks of the type A(4)(AB(2))(4), which have a porphyrin core, and longer (3.9 or 4.5 nm) and shorter (1.6 nm) conjugated chains. Fluorescence measurements revealed that singlet energy is effectively transferred in the assemblies from peripheral benzyl ether units and conjugated chains to the free base porphyrin core.

  DOI：

  10.1021/jo3014512
• 作为产物：
  描述：

  3,5-bis(trimethylsilylethynyl)-1-(3-hydroxy-3-methyl-1-butynyl)benzene 在 potassium carbonate 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 1.0h， 以90%的产率得到4-[3,5-bis(2-ethynyl)phenyl]-2-methyl-3-butyn-2-ol
  参考文献：
  名称：

  Construction of Snowflake-Shaped Dendritic Covalent Assemblies with Rigid Conjugated Networks

  摘要：

  A convergent method for the construction of shape-persistent nanoscale assemblies with conjugated backbones was developed. The copper-free Sonogashira coupling reaction was successfully applied to the formation of multiple covalent connections between conjugated terminals (iodide substituted aryl groups) of AB(2)-type outer components and four conjugated terminals (acetylenic bonds) of an inner A(4)-type core dendrimer. The conjugated networks in the starting components are expanded during the assembly process to afford nanoscale dendritic conjugated networks of the type A(4)(AB(2))(4), which have a porphyrin core, and longer (3.9 or 4.5 nm) and shorter (1.6 nm) conjugated chains. Fluorescence measurements revealed that singlet energy is effectively transferred in the assemblies from peripheral benzyl ether units and conjugated chains to the free base porphyrin core.

  DOI：

  10.1021/jo3014512