2-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11-hexadecafluoro-22-hydroxy-2,13-diiodo-docosyl)-isoindole-1,3-dione | 686286-14-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11-hexadecafluoro-22-hydroxy-2,13-diiodo-docosyl)-isoindole-1,3-dione
• CAS: 686286-14-6
• 化学式: C₃₀H₃₁F₁₆I₂NO₃
• 分子量: 1011.36
• InChiKey: YCYXBYOTMGTEQO-UHFFFAOYSA-N

物化性质

• 沸点：
  634.9±55.0 °C(Predicted)
• 密度：
  1.703±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.87
• 重原子数：
  52.0
• 可旋转键数：
  22.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  57.61
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11-hexadecafluoro-22-hydroxy-2,13-diiodo-docosyl)-isoindole-1,3-dione 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以70%的产率得到2-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11-hexadecafluoro-22-hydroxy-docosyl)-isoindole-1,3-dione
  参考文献：
  名称：

  Synthesis of amino terminated semifluorinated long-chain alkanethiols

  摘要：

  The alpha,omega-diiodoperfluorooctane is added to undecyl-10-en-1-ol through AIBN initiation yielding the monoadduct in good yield (1,2-dichloroethane, 52%). This is added to N-allylphthalimide (AIBN initiation, 1,2-dichloroethane, 81%). The resulting diiodo compound is hydrodeiodinated with Bu3SnH (toluene, 70%) and the alcohol function is converted to thioacetate through the Mitsunobu reaction (PPh3, DIAD, THF, 75%). The two protecting groups, phthalimide and thioacetate, are removed with hydrazine to give the expected amino terminated semifluorinated long-chain alkanethiol (ethanol, 80%). This compound has been designed in order to form mixed fluorinated self-assembled monolayers (SAMs) with semifluorinated long-chain alkanethiol giving access to a new platform system for biosensors. Similar results are reported starting from the alpha,omega-diiodoperfluorohexane. (C) 2003 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2003.08.001
• 作为产物：
  描述：

  1,8-二碘代全氟辛烷 在 偶氮二异丁腈 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 6.0h， 生成 2-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11-hexadecafluoro-22-hydroxy-2,13-diiodo-docosyl)-isoindole-1,3-dione
  参考文献：
  名称：

  Synthesis of amino terminated semifluorinated long-chain alkanethiols

  摘要：

  The alpha,omega-diiodoperfluorooctane is added to undecyl-10-en-1-ol through AIBN initiation yielding the monoadduct in good yield (1,2-dichloroethane, 52%). This is added to N-allylphthalimide (AIBN initiation, 1,2-dichloroethane, 81%). The resulting diiodo compound is hydrodeiodinated with Bu3SnH (toluene, 70%) and the alcohol function is converted to thioacetate through the Mitsunobu reaction (PPh3, DIAD, THF, 75%). The two protecting groups, phthalimide and thioacetate, are removed with hydrazine to give the expected amino terminated semifluorinated long-chain alkanethiol (ethanol, 80%). This compound has been designed in order to form mixed fluorinated self-assembled monolayers (SAMs) with semifluorinated long-chain alkanethiol giving access to a new platform system for biosensors. Similar results are reported starting from the alpha,omega-diiodoperfluorohexane. (C) 2003 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2003.08.001