4-(2-氟乙基)苯甲酸甲酯 | 819883-83-5

• 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: 4-(2-氟乙基)苯甲酸甲酯
• 英文名称: methyl 4-(2-fluoroethyl)benzoate
• CAS: 819883-83-5
• 化学式: C₁₀H₁₁FO₂
• 分子量: 182.195
• InChiKey: PLQNTYFWSCFMQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2-氟乙基)苯甲酸甲酯 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以75%的产率得到(4-(2-fluoroethyl)phenyl)methanol
  参考文献：
  名称：

  New N-substituted 9-azabicyclo[3.3.1]nonan-3α-yl phenylcarbamate analogs as σ2 receptor ligands: Synthesis, in vitro characterization, and evaluation as PET imaging and chemosensitization agents

  摘要：

  A series of N-substituted 9-azabicyclo[3.3.1] nonan-3 alpha-yl phenylcarbamate analogs were synthesized. Among them, WC-26 and WC-59 were identified as the most potent sigma(2) receptor ligands (K-i = 2.58 and 0.82 nM, respectively) with high selectivity against sigma(1) (K-i of sigma(1)/sigma(2) ratio = 557 and 2087, respectively). [F-18] WC-59 was radiolabeled via a nucleophilic substitution of a mesylate precursor by [F-18]fluoride and in vitro direct binding studies of [F-18]WC-59 were conducted using membrane preparations from murine EMT-6 solid breast tumors. The results indicate that [F-18]WC-59 binds specifically to sigma(2) receptors in vitro (K-d = similar to 2 nM). Biodistribution studies of [F-18]WC-59 in EMT-6 tumor-bearing mice indicated that the tracer was a less suitable candidate for clinical imaging studies than existing F-18 labeled sigma(2) receptor ligands. The ability of WC-26 to enhance the cytotoxic effects of the chemotherapy drug, doxorubicin, was evaluated in cell culture using the mouse breast tumor EMT-6 and the human tumor MDA-MB435. WC-26 greatly increased the ability of doxorubicin to kill these two tumor cell lines in vitro. These results indicate that WC-26 is potentially a useful chemosensitizer for the treatment of cancer when combined with conventional chemotherapeutics. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.12.025
• 作为产物：
  描述：

  4-乙烯基苯甲酸 在 硼烷 、 三乙胺 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 23.0h， 生成 4-(2-氟乙基)苯甲酸甲酯
  参考文献：
  名称：

  N-苯基哌嗪类似物作为潜在的多巴胺D3受体配体的合成和体外结合。

  摘要：

  制备了一系列的N-（2-甲氧基苯基）哌嗪和N-（2,3-二氯苯基）哌嗪类似物，并在体外测量了它们对多巴胺D（2），D（3）和D（4）受体的亲和力。还进行了结合研究以确定化合物是否结合sigma（sigma（1）和sigma（2））和血清素（5-HT（1A），5-HT（2A），5-HT（2B），5- HT（2C），5-HT（3），5-HT（4），5-HT（5），5-HT（6）和5-HT（7））受体。当前研究的结果表明，许多化合物（12b，12c，12e和12g）对D（3）具有高亲和力（D（3）受体的K（i）范围从0.3到0.9 nM），而D （2）（D（2）受体的K（i）在40到53 nM之间）和log P值，表明它们应该容易越过血脑屏障（log P = 2.6-3.5）。在这项研究中评估的所有化合物都对5-羟色胺5-HT（1A）受体具有高亲和力。

  DOI：

  10.1016/j.bmc.2004.09.054

文献信息

• Exploiting the trifluoroethyl group as a precatalyst ligand in nickel-catalyzed Suzuki-type alkylations
  作者：Yi Yang、Qinghai Zhou、Junjie Cai、Teng Xue、Yingle Liu、Yan Jiang、Yumei Su、Lungwa Chung、David A. Vicic

  DOI：10.1039/c9sc00554d

  日期：——

  A bis-trifluoroethyl coordinated nickel/bipyridine complex has been developed as efficient precatalyst for diverse Suzuki-type alkylations which features unconventional precatalyst initiation mode.

  已开发出一种双三氟乙基配位的镍/双吡啶配合物，作为高效的预催化剂，用于多样化的铃木型烷基化反应，具有非传统的预催化剂启动模式。
• 一种单氟乙基取代芳香化合物的制备方法
  申请人：四川理工学院

  公开号：CN107628926B

  公开（公告）日：2020-07-28

  本发明提供一种单氟乙基取代芳香化合物的制备方法，属于含氟有机分子制备技术领域。所述制备方法为在反应溶剂及氮气氛围下，以1‑氟‑2‑碘乙烷和经弱碱活化后的芳基硼酸为原料，在镍催化剂和联吡啶类配体的催化体系作用下，加热反应达到终点后，经分离、提纯得到单氟乙基取代芳香化合物。本发明制备方法采用便宜易得的镍催化剂和联吡啶类配体为催化体系，实现单氟乙基向芳香基团的定向引入，从而高效制备获得单氟乙基取代芳香化合物。本方法不仅反应条件温和，原料来源广、成本低，反应步骤简洁，而且反应规模易于放大，产物分离简便，具有适于工业化生产的优势。
• ISOCARBACYCLIN WITH MODIFIED $g(a)-CHAIN AND PROCESS FOR PRODUCING THE SAME
  申请人：TEIJIN LIMITED

  公开号：EP0664281A1

  公开（公告）日：1995-07-26

  An isocarbacyclin with the α-chain modified with phenylene, cycloalkylene or thiophenediyl. It has the activity of inhibiting DNA synthesis of human smooth muscle cells and is expected to inhibit vascular hypertrophy.

  一种α-链经亚苯基、环烷基或噻吩二基修饰的异碳双环化合物。它具有抑制人体平滑肌细胞 DNA 合成的活性，可望抑制血管肥大。
• Evaluation of N-phenyl homopiperazine analogs as potential dopamine D3 receptor selective ligands
  作者：Aixiao Li、Yogesh Mishra、Maninder Malik、Qi Wang、Shihong Li、Michelle Taylor、David E. Reichert、Robert R. Luedtke、Robert H. Mach

  DOI：10.1016/j.bmc.2013.03.074

  日期：2013.6

  A series of N-(2-methoxyphenyl) homopiperazine analogs was prepared and their affinities for dopamine D-2, D-3, and D-4 receptors were measured using competitive radioligand binding assays. Several ligands exhibited high binding affinity and selectivity for the D-3 dopamine receptor compared to the D-2 receptor subtype. Compounds 11a, 11b, 11c, 11f, 11j and 11k had Ki values ranging from 0.7 to 3.9 nM for the D-3 receptor with 30- to 170-fold selectivity for the D-3 versus D-2 receptor. Calculated log P values (logP = 2.6-3.6) are within the desired range for passive transport across the blood-brain barrier. When the binding and the intrinsic efficacy of these phenylhomopiperazines was compared to those of previously published phenylpiperazine analogues, it was found that (a) affinity at D-2 and D-3 dopamine receptors generally decreased, (b) the D-3 receptor binding selectivity (D-2:D-3 K-i value ratio) decreased and, (c) the intrinsic efficacy, measured using a forskolin-dependent adenylyl cyclase inhibition assay, generally increased. (C) 2013 Elsevier Ltd. All rights reserved.
• ISOCARBACYCLIN WITH MODIFIED alpha(a)-CHAIN AND PROCESS FOR PRODUCING THE SAME
  申请人：TEIJIN LIMITED

  公开号：EP0664281B1

  公开（公告）日：1997-05-28