2-(4,4,5,5,6,6,7,7,8,8,9,9-dodecafluoro-20-hydroxy-eicosyl)-isoindole-1,3-dione | 686286-04-4

• 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-dodecafluoro-20-hydroxy-eicosyl)-isoindole-1,3-dione
• 英文别名: 2-(4,4,5,5,6,6,7,7,8,8,9,9-dodecafluoro-20-hydroxyicosyl)isoindole-1,3-dione
• CAS: 686286-04-4
• 化学式: C₂₈H₃₃F₁₂NO₃
• 分子量: 659.556
• InChiKey: OBWAYNNZWAKBFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  44
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  2-(4,4,5,5,6,6,7,7,8,8,9,9-dodecafluoro-20-hydroxy-eicosyl)-isoindole-1,3-dione 在 偶氮二甲酸二异丙酯 、 一水合肼 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 25.0h， 生成 20-amino-12,12,13,13,14,14,15,15,16,16,17,17-dodecafluoro-eicosane-1-thiol
  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：

  N-烯丙基邻苯二甲酰亚胺 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 21.0h， 生成 2-(4,4,5,5,6,6,7,7,8,8,9,9-dodecafluoro-20-hydroxy-eicosyl)-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

文献信息

• Synthesis of amino terminated semifluorinated long-chain alkanethiols
  作者：C. Amato、P. Calas

  DOI：10.1016/j.jfluchem.2003.08.001

  日期：2003.12

  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.