5-氟-2-苯氧基苯胺 | 613662-01-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-氟-2-苯氧基苯胺
• 英文名称: 5-fluoro-2-phenoxyaniline
• CAS: 613662-01-4
• 化学式: C₁₂H₁₀FNO
• mdl: MFCD08687879
• 分子量: 203.216
• InChiKey: RMYDPTVQMJEGLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  5-氟-2-苯氧基苯胺 在 四(三苯基膦)钯 bis(tri-n-butyl)tin 、 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 102.0h， 生成 N-(5-fluoro-2-phenoxyphenyl)-N-(2-iodo-5-methoxybenzyl)acetamide
  参考文献：
  名称：

  N-(5-Fluoro-2-phenoxyphenyl)-N-(2-[¹³¹I]iodo-5-methoxybenzyl)acetamide:  A Potent Iodinated Radioligand for the Peripheral-type Benzodiazepine Receptor in Brain

  摘要：

  To image the peripheral-type benzodiazepine receptor (PBR) in vivo, we previously developed two positron emission tomography (PET) ligands, N-(2-[C-11],5-dimethoxybenzyl)-N-(5-fluoro-2-phenoxyphenyl)acetamide ([C-11]1a) and its [F-18]fluoroethyl analogue ([F-18]1b), for the investigation of PBR in the living human brain. This time, using 1a as a leading compound, we designed two novel iodinated analogues, N-(5-fluoro-2-phenoxyphenyl)-N-(2-iodo-5-methoxybenzyl)acetamide (3a) and N-(2,5-dimethoxybenzyl)-N-(5-iodo-2-phenoxyphenyl)acetamide (3b) for the PBR imaging. Ligands 3 were synthesized by the iodination of tributystannyl precursors 10. Radiolabeling for 3 with I-131 was carried out by the reaction of 10 with [I-131]NaI using H2O2 as an oxidizing agent. In vitro competition experiments determined that 3a exhibited both high affinity and selectivity for PBR (IC50: 7.8 nM) vs CBR (> 1 mu M). Biodistribution study in mice determined that [I-131]3a had a high radioactivity level (1.69% dose/g) in the brain, and its distribution pattern in the brain was consistent with the known distribution of PBR in rodents. Ex vivo autoradiography of the rat brain gave visual evidence that [I-131]3a was a potent and specific radioligand for PBR.

  DOI：

  10.1021/jm061127n
• 作为产物：
  描述：

  4-fluoro-2-nitro-1-phenoxybenzene 在 三氯化铁 、 甲烷 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以96%的产率得到5-氟-2-苯氧基苯胺
  参考文献：
  名称：

  Synthesis ofN-(2,5-dimethoxybenzyl)-N-(5-fluoro-2-phenoxyphenyl)[carbonyl-11C]acetamide ([carbonyl-11C]DAA1106) and analogues using [11C]carbon monoxide and palladium(0) complex

  摘要：

  N-(2,5-二甲氧基苄基)-N-(5-氟-2-苯氧苯基)乙酰胺（DAA1106），一种强效且选择性的外周苯二氮卓受体配体，及其八个结构相关的类似物，使用低浓度的[11C]一氧化碳和微型高压釜技术在羰基位置进行了11C标记。采用组合方法，利用相似的反应条件合成了这些类似物。合成中使用了四(三苯膦)钯介导的羰基化反应，并结合了各种胺和甲基碘或碘苯。所得的11C标记产物具有10-55%的衰变校正放射化学产率，所有情况下最终产物纯度均超过97%。通过单次实验和10µA h轰击，测定了化合物[羰基-11C]DAA1106的比活度。轰击结束后36分钟测得的比活度为455 GBq/µmol。还开发了合成前体和参考化合物的路线。所提出的方法是一种新颖的[羰基-11C]DAA1106及其类似物的合成方法，并能够形成一系列11C标记的DAA1106类似物库，这些类似物可用于优化其作为潜在正电子发射断层扫描示踪剂的性能。版权所有 © 2007 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jlcr.1437
• 作为试剂：
  描述：

  5-Methoxy-2-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-benzaldehyde 、 5-氟-2-苯氧基苯胺 在 5-氟-2-苯氧基苯胺 作用下， 以66的产率得到(5-Fluoro-2-phenoxy-phenyl)-{5-methoxy-2-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-benzyl}-amine
  参考文献：
  名称：

  Phenyloxyaniline derivatives

  摘要：

  本发明涉及苯氧基苯胺衍生物，其生产方法和用途。

  公开号：

  US07803960B2

文献信息

• [EN] NON-STEROIDAL PROGESTERONE RECEPTOR MODULATORS<br/>[FR] MODULATEURS DE RECEPTEUR DE PROGESTERONE NON STEROIDES
  申请人：AKZO NOBEL NV

  公开号：WO2003084963A1

  公开（公告）日：2003-10-16

  The present invention provides compounds according to general Formula (I), a prodrug thereof, a pharmaceutically acceptable salt thereof, or a pharmaceutically acceptable salt of a prodrug thereof. More particularly, the present invention provides high affinity non-steroidal compounds which are agonists, partial agonists or antagonists of the progesterone receptor.

  本发明提供了符合一般式（I）的化合物，其前药，其药学上可接受的盐，或其前药的药学上可接受的盐。更具体地，本发明提供了高亲和力的非类固醇化合物，它们是孕激素受体的激动剂、部分激动剂或拮抗剂。
• Synthesis ofN-(2,5-dimethoxybenzyl)-N-(5-fluoro-2-phenoxyphenyl)[carbonyl-11C]acetamide ([carbonyl-11C]DAA1106) and analogues using [11C]carbon monoxide and palladium(0) complex
  作者：Obaidur Rahman、Bengt Långström

  DOI：10.1002/jlcr.1437

  日期：2007.11

  N-(2,5-Dimethoxybenzyl)-N-(5-fluoro-2-phenoxyphenyl)acetamide (DAA1106), a potent and selective ligand for peripheral benzodiazepine receptor, and eight structurally related analogues were labelled with 11C at the carbonyl position using a low concentration of [11C]carbon monoxide and the micro-autoclave technique. A combinatorial approach was applied to synthesize the analogues using similar reaction conditions. Palladium-mediated carbonylation using tetrakis(triphenylphosphine)palladium, various amines and methyl iodide or iodobenzene was employed in the synthesis. The 11C-labelled products were obtained with 10–55% decay-corrected radiochemical yields and the final product was more than 97% pure in all cases. Specific radioactivity was determined for the compound [carbonyl-11C]DAA1106 using a single experiment and a 10-µA h bombardment. The specific radioactivity, measured 36 min after end of bombardment, was 455 GBq/µmol. Synthetic routes to the precursors and reference compounds were also developed. The presented approach is a novel method for the synthesis of [carbonyl-11C]DAA1106 and its analogues, and allows the formation of a library of 11C-labelled DAA1106 analogues which can be used to optimize the performance as a potential positron emission tomography tracer. Copyright © 2007 John Wiley & Sons, Ltd.

  N-(2,5-二甲氧基苄基)-N-(5-氟-2-苯氧苯基)乙酰胺（DAA1106），一种强效且选择性的外周苯二氮卓受体配体，及其八个结构相关的类似物，使用低浓度的[11C]一氧化碳和微型高压釜技术在羰基位置进行了11C标记。采用组合方法，利用相似的反应条件合成了这些类似物。合成中使用了四(三苯膦)钯介导的羰基化反应，并结合了各种胺和甲基碘或碘苯。所得的11C标记产物具有10-55%的衰变校正放射化学产率，所有情况下最终产物纯度均超过97%。通过单次实验和10µA h轰击，测定了化合物[羰基-11C]DAA1106的比活度。轰击结束后36分钟测得的比活度为455 GBq/µmol。还开发了合成前体和参考化合物的路线。所提出的方法是一种新颖的[羰基-11C]DAA1106及其类似物的合成方法，并能够形成一系列11C标记的DAA1106类似物库，这些类似物可用于优化其作为潜在正电子发射断层扫描示踪剂的性能。版权所有 © 2007 John Wiley & Sons, Ltd.
• Synthesis of [11C]FEDAA1106 as a new PET imaging probe of peripheral benzodiazepine receptor expression
  作者：Min Wang、Mingzhang Gao、Gary D. Hutchins、Qi-Huang Zheng

  DOI：10.1016/j.ejmech.2008.08.001

  日期：2009.6

  promising radioligands for positron emission tomography (PET) imaging of PBR. This study was designed to develop a new radiolabeled analog of [11C]DAA1106 and [18F]FEDAA1106, [11C]FEDAA1106, for PET imaging of PBR expression in brain and cancer. Precursor N-(5-fluoro-2-phenoxyphenyl)-N-(2-(2-fluoroethoxy)-5-hydroxybenzyl)acetamide (9) was synthesized in multiple steps with moderate to high chemical

  周围的苯并二氮杂receptor受体（PBR）与神经炎症和肿瘤进展有关。[ 11 C] DAA1106和[ 18 F] FEDAA1106是用于PBR的正电子发射断层扫描（PET）成像的两种有前途的放射性配体。这项研究旨在开发一种新的放射性标记的[ 11 C] DAA1106和[ 18 F] FEDAA1106，[ 11 C] FEDAA1106的类似物，用于在脑和癌症中对PBR表达进行PET成像。前驱体N-（5-氟-2-苯氧基苯基）-N-（2-（2-氟乙氧基）-5-羟基苄基）乙酰胺（9）分多个步骤合成，化学产率中等至较高。前体9用[ 11 C] CH标记3 OTf，并通过高压液相色谱（HPLC）纯化，以提供目标放射性配体N-（5-氟-2-苯氧基苯基）-N-（2-（2-氟乙氧基）-5- [ 11 C]甲氧基苄基）乙酰胺（ [ 11 C] FEDAA1106，[ 11 C] 10）以60–70％的放射化学收率，基于[
• Non-steroidal progesterone receptor modulators
  申请人：Hermkens Pedro, Harold, Han

  公开号：US20050171087A1

  公开（公告）日：2005-08-04

  The present invention provides compounds according to general Formula (I), a prodrug thereof, a pharmaceutically acceptable salt thereof, or a pharmaceutically acceptable salt of a prodrug thereof. More particularly, the present invention provides high affinity non-steroidal compounds which are agonists, partial agonists or antagonists of the progesterone receptor.

  本发明提供了符合一般式(I)的化合物，其前药，其药学上可接受的盐或其前药的药学上可接受的盐。更具体地，本发明提供了高亲和力的非甾体化合物，其为孕激素受体的激动剂、部分激动剂或拮抗剂。
• AGENTS FOR THERAPY EFFICACY MONITORING AND DEEP TISSUE IMAGING
  申请人：Bornhop J. Darryl

  公开号：US20080031823A1

  公开（公告）日：2008-02-07

  Compounds and methods related to NIR molecular imaging, in-vitro and in-vivo functional imaging, therapy/efficacy monitoring, and cancer and metastatic activity imaging. Compounds and methods demonstrated pertain to the field of peripheral benzodiazepine receptor imaging, metabolic imaging, cellular respiration imaging, cellular proliferation imaging as targeted agents that incorporate signaling agents.

  与近红外分子成像、体外和体内功能成像、治疗/疗效监测以及癌症和转移活动成像相关的化合物和方法。展示的化合物和方法涉及外周苯二氮平受体成像、代谢成像、细胞呼吸成像、细胞增殖成像作为包含信号剂的靶向剂。