methyl 4-(2-fluoroethoxy)benzoate | 132838-34-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4-(2-fluoroethoxy)benzoate
• CAS: 132838-34-7
• 化学式: C₁₀H₁₁FO₃
• 分子量: 198.194
• InChiKey: KODIHNQWZAHXMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-(2-fluoroethoxy)benzoate 在 水 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 4-(2-fluoroethoxy)-N-(4-(4-(2-(2-fluoroethoxy)phenyl)piperazin-1-yl)butyl)benzamide
  参考文献：
  名称：

  Synthesis and Pharmacological Evaluation of Fluorine-Containing D₃ Dopamine Receptor Ligands

  摘要：

  A series of fluorine-containing N-(2-methoxyphenyl)piperazine and N-(2-fluoroethoxy)piperazine analogues were synthesized, and their affinities for human dopamine D-2, D-3, and D-4 receptors were determined. Radioligand binding studies identified five compounds, 18a, 20a, 20c, 20e, and 21e, which bind with high affinity at D-3 (K-i = 0.17-5 nM) and moderate to high selectivity for D-3 VS D-2 receptors (ranging from similar to 25-to 163-fold). These compounds were also evaluated for intrinsic activity at D-2 and D3 receptors using a forskolin-dependent adenylyl cyclase assay. This panel of compounds exhibits varying receptor subtype binding selectivity and intrinsic activity at D-2 VS D-3 receptors. These compounds may be useful for behavioral pharmacology studies on the role of D-2-like dopamine receptors in neuropsychiatric and neurological disorders. Furthermore, compound 20e, which has the highest binding affinity and selectivity for the D-3 receptor (K-i = 0.17 nM for D-3, 163-fold selectivity for D-3 VS D-2 receptors), represents a candidate fluorine-18 radiotracer for in vivo PET imaging studies on the regulation of D-3 receptor expression.

  DOI：

  10.1021/jm101323b
• 作为产物：
  描述：

  1-溴-2-氟乙烷 在 sodium hydride 作用下， 以 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 21.33h， 以85%的产率得到methyl 4-(2-fluoroethoxy)benzoate
  参考文献：
  名称：

  Amino-5,5-diphenylimidazolone derivatives for the inhibition of beta-secretase

  摘要：

  本发明提供了一种I式化合物及其用于治疗、预防或改善患有β-淀粉样蛋白沉积或患者体内β-淀粉样蛋白水平升高的疾病或紊乱的用途。

  公开号：

  US20050282825A1

文献信息

• Radiosynthesis of (±)-(2-((4-(2-[¹⁸F]fluoro-ethoxy)phenyl)bis(4-methoxy-phenyl)methoxy)ethylpiperidine-3-carboxylic acid: a potential GAT-3 PET ligand to study GABAergic neuro-transmission<i>in vivo</i>
  作者：Ralf Schirrmacher、Wilhelm Hamkens、Markus Piel、Ulrich Schmitt、Hartmut Lüddens、Christoph Hiemke、Frank Rösch

  DOI：10.1002/jlcr.492

  日期：2001.8

  A dysfunction of GABAergic neurotransmission is related to diseases such as epilepsy, Huntington-disease and Parkinson-syndrome. A new 18F-fluorine labelled GABA transporter ligand for the GABA-transporter subtype GAT-3 was developed which may allow the in vivo visualisation of GABAergic neurotransmission. The precursors ethyl (2-(4-hydroxyphenyl)bis(4-methoxyphenyl)-methoxy)ethyl)-piperidine-3-carboxylate and ethyl(2-((4-(2-tosylethoxy)phenyl)-bis(4-methoxyphenyl)-methoxy) ethyl)-piperidine3-carboxylate were synthesised and labelled by the use of 2-[18F]fluoroethyltosylate or [18F]fluoride. Subsequent cleavage of the ester moiety gave the final product (±)-(2-((4-(2-[18F]fluoroethoxy)phenyl)bis(4-methoxy-phenyl)methoxy)ethyl)piperidine-3-carboxylic acid in a decay corrected yield of 33–36%. Preliminary biodistribution kinetics were determined with BALB/c mice ex vivo for brain, liver, kidney, spleen, blood and bone. (2-((4-(2-[18F]fluoroethoxy)-phenyl)bis(4-methoxyphenyl)methoxy)-ethyl) piperidine-3-carboxylic acid showed a maximum brain uptake after 1 h p.i. of about 0.3% ID/g. Copyright © 2001 John Wiley & Sons, Ltd.

  GABA能神经传递的功能障碍与癫痫、亨廷顿舞蹈病和帕金森综合征等疾病有关。开发了一种新的18F氟标记的GABA转运蛋白配体，用于GABA转运蛋白亚型GAT-3，这可能允许在体内可视化GABA能神经传递。合成了前体化合物ethyl (2-(4-hydroxyphenyl)bis(4-methoxyphenyl)-methoxy)ethyl)-piperidine-3-carboxylate和ethyl(2-((4-(2-tosylethoxy)phenyl)-bis(4-methoxyphenyl)-methoxy) ethyl)-piperidine3-carboxylate，并通过使用2-[18F]fluoroethyltosylate或[18F]氟化物进行了标记。随后，酯基的裂解得到了最终产物(±)-(2-((4-(2-[18F]fluoroethoxy)phenyl)bis(4-methoxy-phenyl)methoxy)ethyl)piperidine-3-carboxylic acid，衰减修正后的产率为33–36%。对BALB/c小鼠进行的初步生物分布动力学研究显示，该化合物在注射后1小时脑内摄取达到最大值，大约为0.3% ID/g。版权© 2001 John Wiley & Sons, Ltd.
• Electro‐Oxidative Selective Esterification of Methylarenes and Benzaldehydes
  作者：Congjun Yu、Bünyamin Özkaya、Frederic W. Patureau

  DOI：10.1002/chem.202005158

  日期：2021.2.19

  A mild and green electro‐oxidative protocol to construct aromatic esters from methylarenes and alcohols is herein reported. Importantly, the reaction is free of metals, chemical oxidants, bases, acids, and operates at room temperature. Moreover, the design of the electrolyte was found critical for the oxidation state and structure of the coupling products, a rarely documented effect. This electro‐oxidative

  本文报道了一种温和的绿色电氧化方案，可从甲基芳烃和醇中构建芳香族酯。重要的是，该反应不含金属，化学氧化剂，碱，酸，并且在室温下进行。此外，发现电解质的设计对于偶联产物的氧化态和结构至关重要，很少有文献记载这种作用。这种电氧化偶联过程还表现出对许多易碎的易氧化官能团（例如羟基，醛，烯烃，炔烃以及邻近的苄基位置）的出色耐受性。此外，在该电-氧化偶联反应过程中还保留了一些手性醇的对映异构体富集，这使其整体上成为有前途的合成工具。
• ISATIN ANALOGUES AND USES THEREFOR
  申请人：Mach Robert H.

  公开号：US20090068105A1

  公开（公告）日：2009-03-12

  Novel isatin analogues, including isatin analogues comprising Michael Acceptors (IMAs) are disclosed. Further disclosed are methods of synthesis of the isatin analogues, and uses of the analogues, including inhibition of caspase-3 and caspase-7, and in vivo imaging of apoptosis by Positron emission tomography (PET) or Single Photon Emission Computed Tomography (SPECT).

  揭示了新颖的吲哚类似物，包括具有Michael受体的吲哚类似物（IMAs）。进一步揭示了吲哚类似物的合成方法，以及类似物的用途，包括抑制caspase-3和caspase-7，以及通过正电子发射断层扫描（PET）或单光子发射计算机断层扫描（SPECT）对凋亡进行体内成像。
• Design, Synthesis, and <i>In Vitro</i> and <i>In Vivo</i> Evaluation of an ¹⁸F-Labeled Sphingosine 1-Phosphate Receptor 1 (S1P₁) PET Tracer
  作者：Adam J. Rosenberg、Hui Liu、Hongjun Jin、Xuyi Yue、Sean Riley、Steven J. Brown、Zhude Tu

  DOI：10.1021/acs.jmedchem.6b00390

  日期：2016.7.14

  identified as a therapeutic target for various diseases, a PET tracer for S1P1 would be a useful tool. Fourteen fluorine-containing analogues of S1P ligands were synthesized and their in vitro binding potency measured; four had high potency and selectivity for S1P1 (S1P1 IC50 < 10 nM, >100-fold selectivity for S1P1 over S1P2 and S1P3). The most potent ligand, 28c (IC50 = 2.63 nM for S1P1) was 18F-labeled and

  1-磷酸鞘氨醇受体 1 (S1P 1 ) 在炎症反应中发挥着关键的信号传导作用；由于 S1P 1调节已被确定为多种疾病的治疗靶点，因此 S1P 1的 PET 示踪剂将是一种有用的工具。合成了14种S1P配体的含氟类似物并测量了它们的体外结合效力；四种对 S1P 1具有高效力和选择性（S1P 1 IC 50 < 10 nM，对 S1P 1的选择性是 S1P 2和 S1P 3的 >100 倍）。最有效的配体28c （S1P 1的IC 50 = 2.63 nM）被18 F标记并在LPS诱导的急性肝损伤的小鼠模型中进行评估以确定其S1P 1结合特异性。生物分布、放射自显影和 microPET 成像结果显示，LPS 治疗小鼠肝脏中的 [ 18 F] 28c积累量高于对照组。通过免疫组织化学分析 (IHC) 证实了 LPS 模型中 S1P 1表达的增加。这些数据表明[ 18 F] 28c是一种S1P 1
• Pesticidal 2-fluoroethyl ethers
  申请人：FMC Corporation

  公开号：US04960884A1

  公开（公告）日：1990-10-02

  Pesticidal mono-, di-, and tri-2-fluoroethyl ethers of the formula R.sup.1 R.sup.2.sub.m Ar(OCH.sub.2 CH.sub.2 F).sub.n, compositions thereof and their insecticidal, acaricidal and nematicidal uses are described and claimed.

  描述和声明了化学式为R.sup.1 R.sup.2.sub.m Ar(OCH.sub.2 CH.sub.2 F).sub.n的杀虫单、二和三-2-氟乙基醚，以及它们的组合物及其杀虫、杀螨和杀线虫用途。