2,3,5,6-四氟苯基(2-硝基-1H-咪唑-1-基)乙酸酯 | 199734-70-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2,3,5,6-四氟苯基(2-硝基-1H-咪唑-1-基)乙酸酯
• 英文名称: 2,3,5,6-tetrafluorophenyl 2-(2-nitroimidazol-1-yl)acetate
• 英文别名: 2,3,5,6-tetrafluorophenyl (2-nitroimidazol-1-yl)acetate；2,3,5,6-tetrafluorophenyl 2-(2-nitro-imidazol-1-yl)-acetate；1H-Imidazole-1-acetic acid, 2-nitro-, 2,3,5,6-tetrafluorophenyl ester；(2,3,5,6-tetrafluorophenyl) 2-(2-nitroimidazol-1-yl)acetate
• CAS: 199734-70-8
• 化学式: C₁₁H₅F₄N₃O₄
• 分子量: 319.172
• InChiKey: YCPHYOBSBOVNNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  89.9
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-氟乙胺 、 2,3,5,6-四氟苯基(2-硝基-1H-咪唑-1-基)乙酸酯 以 乙腈 为溶剂， 反应 0.17h， 生成 N-(2-氟乙基)-2-(2-硝基-1H-咪唑-1-基)乙酰胺
  参考文献：
  名称：

  Tewson, T. J., Journal of labelled compounds and radiopharmaceuticals, 1997, vol. 40, p. 56 - 57

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3,5,6-四氟苯酚 在 三氟化硼乙醚 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 48.0h， 生成 2,3,5,6-四氟苯基(2-硝基-1H-咪唑-1-基)乙酸酯
  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

• A simplified synthesis of 2,3,5,6-tetrafluorophenyl 2-(2-nitroimidazol-1-yl) acetate
  作者：Hanna Wilson

  DOI：10.1002/jlcr.691

  日期：2003.5

  2,3,5,6-Tetrafluorophenyl 2-(2-nitroimidazol-1-yl) acetate has been synthesized via an improved route which involves the direct coupling of 2-(2-nitroimidazol-1-yl) acetic acid with 2,3,5,6-tetrafluorophenol. Copyright © 2003 John Wiley & Sons, Ltd.

  2,3,5,6-四氟苯基 2-(2-硝基咪唑-1-基)乙酸酯是通过改进的路线合成的，该路线涉及 2-(2-硝基咪唑-1-基)乙酸与 2,3,5,6-四氟苯酚的直接偶联。版权所有 © 2003 John Wiley & Sons, Ltd.
• METHODS FOR PREPARING PERFLUORINATED [18 F]-RADIOLABELLED NITROIMIDAZOLE DERIVATIVES FOR CELLULAR HYPOXIA DETECTION
  申请人：UNIVERSITE CATHOLIQUE DE LOUVAIN

  公开号：EP1202945B1

  公开（公告）日：2005-08-17
• US7108846B1
  申请人：——

  公开号：US7108846B1

  公开（公告）日：2006-09-19
• [EN] METHODS FOR PREPARING PERFLUORINATED [<18>F]-RADIOLABELLED NITROIMIDAZOLE DERIVATIVES FOR CELLULAR HYPOXIA DETECTION<br/>[FR] PROCEDES DE PREPARATION DE DERIVES DE NITRO-IMIDAZOLE PERFLUORES RADIOMARQUES AU [<18>F] SERVANT A DETECTER L'HYPOXIE CELLULAIRE
  申请人：UNIV LOUVAIN

  公开号：WO2001012575A1

  公开（公告）日：2001-02-22

  The present invention relates to chemical synthesis of radiolabelled perfluorinated bioactive compounds. More particularly, the present invention relates to radiolabelled compounds to be used as indicators for tissue hypoxia. More particularly, the present invention relates to the synthesis and the use of [18F] labelled perfluorinated nitroimidazole compounds having an incorporation of [18F] atoms characterized by a specific radioactivity of the compound comprised between 1 and 30 Ci/mmol, preferably between 1 and 20 Ci/mmol, preferably 1 and 10 Ci/mmol. More particularly to [18F] labelled EF3 or [18F] labelled EF5. The present invention also relates to a method for the detection of tissue hypoxia in a patient comprising introducing an [18F] labelled nitroimidazole compound into said patient, imaging tissue hypoxia in said patient, and, quantifying tissue hypoxia in said patient.
• Synthesis of [18F]-labeled EF3 [2-(2-nitroimidazol-1-yl)-N-(3,3,3-trifluoropropyl)-acetamide], a marker for PET detection of hypoxia
  作者：Olivier Josse、Daniel Labar、Benoit Georges、Vincent Grégoire、Jacqueline Marchand-Brynaert

  DOI：10.1016/s0968-0896(00)00279-0

  日期：2001.3

  [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.