(1E,5S)-5-(2-fluoroethoxy)cyclooctene

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1E,5S)-5-(2-fluoroethoxy)cyclooctene
• 化学式: C₁₀H₁₇FO
• 分子量: 172.243
• InChiKey: BKPCVKMDKAOKSQ-TXXBHVLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1E,5S)-5-(2-fluoroethoxy)cyclooctene 以 氘代乙腈 、 重水 、 乙腈 为溶剂， 反应 48.0h， 生成 8-(2-fluoroethoxy)-1,4-di(pyridin-2-yl)-2,4a,5,6,7,8,9,10-octahydrocycloocta[d]pyridazine
  参考文献：
  名称：

  [EN] TETRAZINE-TRANS-CYCLOOCTENE LIGATION FOR THE RAPID CONSTRUCTION OF RADIONUCLIDE LABELED PROBES
  [FR] LIGATURE TÉTRAZINE-TRANS-CYCLOOCTÈNE POUR LA CONSTRUCTION RAPIDE DE SONDES MARQUÉES PAR UN RADIONUCLÉIDE

  摘要：

  公开号：

  WO2012012612A3
• 作为产物：
  描述：

  (Z)-cyclooct-4-enol 在 苯甲酸甲酯 、 N-甲基-N-亚硝基对甲苯磺酰胺 、 四丁基氟化铵 、 sodium hydride 、 二异丁基氢化铝 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 正己烷 、 乙腈 为溶剂， 反应 21.5h， 生成 (1E,5S)-5-(2-fluoroethoxy)cyclooctene
  参考文献：
  名称：

  [EN] TETRAZINE-TRANS-CYCLOOCTENE LIGATION FOR THE RAPID CONSTRUCTION OF RADIONUCLIDE LABELED PROBES
  [FR] LIGATURE TÉTRAZINE-TRANS-CYCLOOCTÈNE POUR LA CONSTRUCTION RAPIDE DE SONDES MARQUÉES PAR UN RADIONUCLÉIDE

  摘要：

  公开号：

  WO2012012612A3

文献信息

• Tetrazine-trans-cyclooctene Ligation for the Rapid Construction of Radionuclide Labeled Probes
  申请人：Fox Joseph M.

  公开号：US20130266512A1

  公开（公告）日：2013-10-10

  A Diels-Alder adduct of a trans-cyclooctene with a tetrazine is provided, wherein the adduct bears a substituent labeled with a radionuclide. A method of producing a PET or other image of an organ in an animal or human includes forming the Diels-Alder adduct in the animal or human. Trans-cyclooctenes and tetrazines suitable for preparing the adducts are provided.

  提供了一种具有放射性核素标记取代基的顺-环辛烯和四氮杂环的Diels-Alder加合物，其中该加合物在动物或人体内形成。一种制备动物或人体器官PET或其他图像的方法包括在动物或人体内形成Diels-Alder加合物。提供了适用于制备加合物的顺-环辛烯和四氮杂环。
• Tetrazine-trans-cyclooctene ligation for the rapid construction of radionuclide labeled probes
  申请人：Fox Joseph M.

  公开号：US10434197B2

  公开（公告）日：2019-10-08

  A Diels-Alder adduct of a trans-cyclooctene with a tetrazine is provided, wherein the adduct bears a substituent labeled with a radionuclide. A method of producing a PET or other image of an organ in an animal or human includes forming the Diels-Alder adduct in the animal or human. Trans-cyclooctenes and tetrazines suitable for preparing the adducts are provided.

  提供了一种反式环辛烯与四嗪的 Diels-Alder 加合物，其中该加合物带有用放射性核素标记的取代基。在动物或人体内生成 PET 或其他器官图像的方法包括在动物或人体内形成 Diels-Alder 加合物。提供了适用于制备加合物的反式环辛烯和四嗪。
• Tetrazine-trans-cyclooctene ligation for the rapid construction of integrin αvβ3 targeted PET tracer based on a cyclic RGD peptide
  作者：Ramajeyam Selvaraj、Shuanglong Liu、Matthew Hassink、Chiun-wei Huang、Li-peng Yap、Ryan Park、Joseph M. Fox、Zibo Li、Peter S. Conti

  DOI：10.1016/j.bmcl.2011.04.116

  日期：2011.9

  Labeling biomolecules with F-18 is usually done through coupling with prosthetic groups, which generally requires several time-consuming radiosynthetic steps resulting in low labeling yield. Recently, the tetrazine-trans-cyclooctene ligation has been introduced as a method of bioconjugation that proceeds with fast reaction rates without need for catalysis. Herein, we report the development of an extremely fast and efficient method for generating F-18 labeled probes based on the tetrazine-trans-cyclooctene ligation. Starting with only 30 mu g (78 mu M) of a tetrazine-RGD conjugate and 2 mCi (5 mu M) of F-18-trans-cyclooctene, the F-18 labeled RGD peptide could be obtained in more than 90% yield within five minutes. The F-18 labeled RGD peptide demonstrated prominent tumor uptake in vivo. The receptor specificity was confirmed by blocking experiments. These results successfully demonstrate that the tetrazine-trans-cyclooctene ligation serves as an efficient labeling method for PET probe construction. (C) 2011 Elsevier Ltd. All rights reserved.
• TETRAZINE-TRANS-CYCLOOCTENE LIGATION FOR THE RAPID CONSTRUCTION OF RADIONUCLIDE LABELED PROBES
  申请人：University Of Delaware

  公开号：EP2595967B1

  公开（公告）日：2016-03-23
• [EN] TETRAZINE-TRANS-CYCLOOCTENE LIGATION FOR THE RAPID CONSTRUCTION OF RADIONUCLIDE LABELED PROBES<br/>[FR] LIGATURE TÉTRAZINE-TRANS-CYCLOOCTÈNE POUR LA CONSTRUCTION RAPIDE DE SONDES MARQUÉES PAR UN RADIONUCLÉIDE
  申请人：UNIV DELAWARE

  公开号：WO2012012612A3

  公开（公告）日：2012-05-24