thioacetic acid 22-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-12,12,13,13,14,14,15,15,16,16,17,17,18,18,19,19-hexadecafluoro-docosyl ester | 686286-24-8

• 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: thioacetic acid 22-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-12,12,13,13,14,14,15,15,16,16,17,17,18,18,19,19-hexadecafluoro-docosyl ester
• CAS: 686286-24-8
• 化学式: C₃₂H₃₅F₁₆NO₃S
• 分子量: 817.675
• InChiKey: MKVMHFVWKYINQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.33
• 重原子数：
  53.0
• 可旋转键数：
  23.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  54.45
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  thioacetic acid 22-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-12,12,13,13,14,14,15,15,16,16,17,17,18,18,19,19-hexadecafluoro-docosyl ester 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以80%的产率得到22-amino-12,12,13,13,14,14,15,15,16,16,17,17,18,18,19,19-hexadecafluoro-docosane-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：

  1,8-二碘代全氟辛烷 在 偶氮二异丁腈 、 偶氮二甲酸二异丙酯 、 三正丁基氢锡 、 三苯基膦 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 37.0h， 生成 thioacetic acid 22-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-12,12,13,13,14,14,15,15,16,16,17,17,18,18,19,19-hexadecafluoro-docosyl ester
  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