[18F]-N-(3,3,3-trifluoropropyl)phthalimide | 347190-24-3

• 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: [18F]-N-(3,3,3-trifluoropropyl)phthalimide
• 英文别名: [18F1]-N-(3,3,3-trifluoropropyl)phthalimide
• CAS: 347190-24-3
• 化学式: C₁₁H₈F₃NO₂
• 分子量: 242.187
• InChiKey: AVCRBZGXNDAFND-DWSYCVKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.24
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  37.38
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  [18F]-N-(3,3,3-trifluoropropyl)phthalimide 在 一水合肼 作用下， 反应 0.17h， 生成 [18F]-3,3,3-trifluoropropylamine
  参考文献：
  名称：

  Synthesis of [18F]-labeled EF3 [2-(2-nitroimidazol-1-yl)-N-(3,3,3-trifluoropropyl)-acetamide], a marker for PET detection of hypoxia

  摘要：

  [F-18]-2-(2-Nitroimidazol-1-yl)-N-(3,3,3-trifluoropropyl)-acetamide ([F-18]-EF3) has been prepared, in 65% chemical yield and 5% radiochemical yield, by coupling 2,3,5,6-tetrafluorophenyl 2-(2-nitroimidazol-1-yl) acetate 1 with [F-18]-3,3,3-trifluoropropylamine 7. This original radiolabelled key-synthon was obtained in 40% overall chemical yield by oxidative [F-18]-fluorodesulfurization of ethyl N-phthalimido-3-aminopropane dithioate 4, followed by deprotection with hydrazine of the resulting [F-18]-N-phthalimido-3,3,3-trifluoropropylamine 5. All the process was performed within 90 min, from the [F-18]-HF production in the cyclotron to the purification of the final target. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00279-0
• 作为产物：
  描述：

  ethyl 3-phthalimidopropanedithioate 在 hydrogen fluoride/pyridine complex 、 lindane 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 [18F]-N-(3,3,3-trifluoropropyl)phthalimide
  参考文献：
  名称：

  Synthesis of [18F]-labeled EF3 [2-(2-nitroimidazol-1-yl)-N-(3,3,3-trifluoropropyl)-acetamide], a marker for PET detection of hypoxia

  摘要：

  [F-18]-2-(2-Nitroimidazol-1-yl)-N-(3,3,3-trifluoropropyl)-acetamide ([F-18]-EF3) has been prepared, in 65% chemical yield and 5% radiochemical yield, by coupling 2,3,5,6-tetrafluorophenyl 2-(2-nitroimidazol-1-yl) acetate 1 with [F-18]-3,3,3-trifluoropropylamine 7. This original radiolabelled key-synthon was obtained in 40% overall chemical yield by oxidative [F-18]-fluorodesulfurization of ethyl N-phthalimido-3-aminopropane dithioate 4, followed by deprotection with hydrazine of the resulting [F-18]-N-phthalimido-3,3,3-trifluoropropylamine 5. All the process was performed within 90 min, from the [F-18]-HF production in the cyclotron to the purification of the final target. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00279-0

文献信息

• Perfluorinated markers for hypoxia detection: synthesis of sulfur-containing precursors and [18F]-labelling
  作者：Arnaud Cheguillaume、Jacques Gillart、Daniel Labar、Vincent Grégoire、Jacqueline Marchand-Brynaert

  DOI：10.1016/j.bmc.2004.11.010

  日期：2005.2

  sequence starting from N-phthalimido-beta-alanine allows the preparation of a new trithioorthoester as valuable precursor of the synthesis of [18F]-3,3,3-trifluoropropylamine, a convenient radiolabelled intermediate for [18F]-EF3. A five-step sequence for the preparation of methyl 4-phthalimido-2,2-difluoropropanedithioate from ethyl 2,2-difluoropropanoate, via the key conversion step of alpha,alpha'-difluorothioamidate

  描述了用于氧化氟脱硫反应的[18F]标记的两种新型硫化前体的合成途径。从N-邻苯二甲酰亚胺基-β-丙氨酸开始的三步序列允许制备新的三硫原酸酯，作为[18F] -3,3,3-三氟丙胺合成的有价值的前体，[18F] -3,3,3-三氟丙胺是方便的放射性标记的[18F] -EF3中间体。通过2，2-二氟丙酸乙酯通过关键的将α，α'-二氟硫代酰胺酸酯转化为相应的α，α'-二氟二硫代酸酯和还介绍了其在[18F]放射化学中用作氧化氟代脱硫前体的最初结果。