12-bromo-N-[4-[2-[4-(5,5-dimethyl-1,3-dioxan-2-yl)-2,5-dioctoxyphenyl]ethynyl]phenyl]dodecanamide | 711013-49-9

• 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: 12-bromo-N-[4-[2-[4-(5,5-dimethyl-1,3-dioxan-2-yl)-2,5-dioctoxyphenyl]ethynyl]phenyl]dodecanamide
• CAS: 711013-49-9
• 化学式: C₄₈H₇₄BrNO₅
• 分子量: 825.023
• InChiKey: GKSNEUOMFDIDJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.5
• 重原子数：
  55
• 可旋转键数：
  31
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  12-bromo-N-[4-[2-[4-(5,5-dimethyl-1,3-dioxan-2-yl)-2,5-dioctoxyphenyl]ethynyl]phenyl]dodecanamide 在 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 5.0h， 以85%的产率得到12-bromo-N-[4-[2-(4-formyl-2,5-dioctoxyphenyl)ethynyl]phenyl]dodecanamide
  参考文献：
  名称：

  Electrochemical Charging of a Fullerene-Functionalized Self-Assembled Monolayer on Au(111)

  摘要：

  A fullerene derivative 10 with a terminal thiol group dissolves easily in common organic solvents and forms a densely packed self-assembled monolayer on gold surfaces. The functionalization of C-60 is based on the 1,3-dipolar cycloaddition of the azomethine ylide generated in situ from the corresponding aldehyde and N-methylglycine. The monolayers were characterized by grazing angle reflectance FTIR spectroscopy, scan tunneling microscopy, and cyclic voltammetry. The cyclic voltammogram of a SAM of 10 showed two well-resolved reversible cathodic waves corresponding to the first two one-electron reductions of the fullerene fragment.

  DOI：

  10.1021/jo049939j
• 作为产物：
  描述：

  2,5-bis(octyloxy)-4-[(triisopropylsilyl)ethynyl]benzaldehyde 在 N-甲基吗啉 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 2-氯-4,6-二甲氧基-1,3,5-三嗪 、 四丁基氟化铵 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 52.5h， 生成 12-bromo-N-[4-[2-[4-(5,5-dimethyl-1,3-dioxan-2-yl)-2,5-dioctoxyphenyl]ethynyl]phenyl]dodecanamide
  参考文献：
  名称：

  Electrochemical Charging of a Fullerene-Functionalized Self-Assembled Monolayer on Au(111)

  摘要：

  A fullerene derivative 10 with a terminal thiol group dissolves easily in common organic solvents and forms a densely packed self-assembled monolayer on gold surfaces. The functionalization of C-60 is based on the 1,3-dipolar cycloaddition of the azomethine ylide generated in situ from the corresponding aldehyde and N-methylglycine. The monolayers were characterized by grazing angle reflectance FTIR spectroscopy, scan tunneling microscopy, and cyclic voltammetry. The cyclic voltammogram of a SAM of 10 showed two well-resolved reversible cathodic waves corresponding to the first two one-electron reductions of the fullerene fragment.

  DOI：

  10.1021/jo049939j

文献信息

• Electrochemical Charging of a Fullerene-Functionalized Self-Assembled Monolayer on Au(111)
  作者：Tao Gu、James K. Whitesell、Marye Anne Fox

  DOI：10.1021/jo049939j

  日期：2004.6.1

  A fullerene derivative 10 with a terminal thiol group dissolves easily in common organic solvents and forms a densely packed self-assembled monolayer on gold surfaces. The functionalization of C-60 is based on the 1,3-dipolar cycloaddition of the azomethine ylide generated in situ from the corresponding aldehyde and N-methylglycine. The monolayers were characterized by grazing angle reflectance FTIR spectroscopy, scan tunneling microscopy, and cyclic voltammetry. The cyclic voltammogram of a SAM of 10 showed two well-resolved reversible cathodic waves corresponding to the first two one-electron reductions of the fullerene fragment.