3-(4-氟苯基)-3-苯丙酸 | 362-86-7

• 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: 3-(4-氟苯基)-3-苯丙酸
• 英文名称: 3-(4-fluorophenyl)-3-phenylpropanoic acid
• CAS: 362-86-7
• 化学式: C₁₅H₁₃FO₂
• 分子量: 244.265
• InChiKey: NKBOILGAWSETPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2916399090

反应信息

• 作为反应物：
  描述：

  3-(4-氟苯基)-3-苯丙酸 生成 3-(4-氟苯基)茚满-1-酮
  参考文献：
  名称：

  不饱和酰卤的反应-IV 1：双官能肉桂酰氯对单卤代苯的竞争性弗里德-克拉斯酰化和烷基化

  摘要：

  已经研究了氯化铝催化的单卤代苯与肉桂酰氯的酰化和烷基化。在严格均质的条件下，相对于酰化而言，烷基化越来越受到关注，因为酰化是沿着该系列的主要反应：苯<氟苯<溴代苯<氯代苯。更改为非均相条件（使用CS 2作为稀释剂的过量催化剂）保留了该顺序，但伯烷基化相对增强。在均相反应中加入硝基苯比烷基化更能抑制烷基化。

  DOI：

  10.1016/0040-4020(78)88113-7
• 作为产物：
  描述：

  Alpha-氯-Alpha-苯基-4-氟甲苯 在 氢氧化钾 、 sodium hydride 、 sodium iodide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 50.17h， 生成 3-(4-氟苯基)-3-苯丙酸
  参考文献：
  名称：

  Ring-substituted histaprodifen analogues as partial agonists for histamine H1 receptors: synthesis and structure–activity relationships

  摘要：

  Thirteen racemic benzene ring-substituted analogues of histaprodifen (8a; 2-[2-(3,3-diphenylpropyl)-1H-imidazol-4-yl]ethanamine), a novel lead for potent and selective histamine H-1-receptor agonists, have been prepared from substituted 4,4-diphenylbutyronitriles 5 via cyclization of the corresponding methyl butyrimidates 6 with 2-oxo-4-phthalimido-1-butyl acetate in liquid ammonia, followed by deprotection. Nitriles 5 were accessible by alkylation of either substituted diphenylmethanes with 3-bromopropionitrile or diethyl malonate with substituted 1-chloro-diphenylmethanes and subsequent standard reactions. The title compounds 8 displayed partial agonism on contractile H-1 receptors of the guinea-pig ileum (E-max = 2-98% relative to histamine) and, compared with the endogenous agonist, were endowed with agonist potencies of 4-92%. The meta fluorinated (gc) and meta chlorinated (8f) analogues showed the highest relative potency in this series (95% confidence Limits 85-99% and 78-102%), but did not exceed the value of the lead 8a (99-124%). Compound 8c (2-[2-[3-(3-fluorophenyl)-3-phenylpropyl]-1H-imidazol-4-yl]ethanamine) was a partial agonist at contractile H-1 receptors of the guinea-pig aorta (relative potency 154% vs. 100% for histamine) and at relaxation-mediating endothelial H-1 receptors of the rat aorta (relative potency 556% vs. 100% for histamine) and matched with the functional behaviour of 8a. Agonism observed for each compound was sensitive to blockade by the selective H-1-receptor antagonist mepyramine (pA(2) approximate to 9 (guinea-pig) and pA(2) approximate to 8 (rat aorta)). All histaprodifen analogues 8 stimulated neither histaminergic H-2/H-3, nor cholinergic M-3 receptors. They displayed only low to moderate affinity for these sites (H-2: pD'(2), < 5; H-3/M-3: pA(2) < 6). With regard to the substitution pattern on the benzene ring, there was no correlation between the histaprodifen series and the corresponding derivatives of another selective H-1-receptor agonist, viz. 2-phenylhistamine. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)00105-7

文献信息

• Pd(II)/Bipyridine-Catalyzed Conjugate Addition of Arylboronic Acids to α,β-Unsaturated Carboxylic Acids. Synthesis of β-Quaternary Carbons Substituted Carboxylic Acids
  作者：Rui Liu、Zhenyu Yang、Yuxin Ni、Kaixuan Song、Kai Shen、Shaohui Lin、Qinmin Pan

  DOI：10.1021/acs.joc.7b01248

  日期：2017.8.4

  Pd(II)/bipyridine-catalyzed conjugate addition of arylboronic acids to α,β-unsaturated carboxylic acids (including β,β-disubstituted acrylic acids) was developed and optimized, which provided a mild and convenient method for the highly challenging synthesis of β-quaternary carbons substituted carboxylic acids.

  开发并优化了Pd（II）/联吡啶催化的芳基硼酸向α，β-不饱和羧酸（包括β，β-二取代的丙烯酸）的共轭加成反应，为高难度的β合成提供了温和而便捷的方法-季碳取代的羧酸。
• Acylguanidines as Bioisosteres of Guanidines: <i>N</i>^G-Acylated Imidazolylpropylguanidines, a New Class of Histamine H₂ Receptor Agonists
  作者：Prasanta Ghorai、Anja Kraus、Max Keller、Carsten Götte、Patrick Igel、Erich Schneider、David Schnell、Günther Bernhardt、Stefan Dove、Manfred Zabel、Sigurd Elz、Roland Seifert、Armin Buschauer

  DOI：10.1021/jm800841w

  日期：2008.11.27

  demonstrated by HPLC-MS, the acylguanidines (bioisosteres of the alkylguanidines) were absorbed from the gut of mice and detected in brain. In GTPase assays using recombinant receptors, acylguanidines were more potent at the guinea pig than at the human H2R. At the hH1R and hH3R, the compounds were weak to moderate antagonists or partial agonists. Moreover, potent partial hH4R agonists were identified. Receptor

  N1-芳基（杂芳基）烷基-N2- [3-（1H-咪唑-4-基）丙基]胍是有效的组胺H2受体（H2R）激动剂，但由于缺乏口服生物利用度和CNS渗透性而削弱了它们的适用性。为了改善药代动力学，我们在胍基部分附近引入了羰基而不是亚甲基，从而将新型H2R激动剂的碱性降低了4-5个数量级。一些具有一个苯环的酰基胍比其二芳基类似物甚至更有效。如通过HPLC-MS证明的，酰基胍（烷基胍的生物等排体）从小鼠的肠中吸收并在脑中检测到。在使用重组受体的GTPase检测中，豚鼠的酰基胍比人的H2R更有力。在hH1R和hH3R处，这些化合物对中度拮抗剂或部分激动剂均弱。而且，确定了有效的部分hH4R激动剂。受体亚型的选择性取决于咪唑基丙基胍基团（特权结构），为包括强效H4R激动剂在内的独特药理学手段开辟了道路。
• Cationic Pd(II)/bipyridine-catalyzed conjugate addition of arylboronic acids to α,β-unsaturated carboxylic acids in aqueous media
  作者：Yuxin Ni、Kaixuan Song、Kai Shen、Zhenyu Yang、Rui Liu、Shaohui Lin、Qinmin Pan

  DOI：10.1016/j.tetlet.2018.02.013

  日期：2018.3

  An in-situ generated cationic Pd(II)/bipyridine-catalyzed conjugate addition of arylboronic acids to α,β-unsaturated carboxylic acids in water was developed and optimized. For most substrates, nearly quantitative yields were given, and the products can be purified by simple washing without column chromatography. The reaction can be scaled up to 1.0 g easily with excellent yields. Also the loading of

  开发并优化了芳基硼酸到水中α，β-不饱和羧酸的阳离子Pd（II）/联吡啶催化的阳离子共轭加成反应。对于大多数底物，给出了接近定量的收率，并且可以通过不经柱色谱的简单洗涤来纯化产物。可以轻松地将反应放大至1.0 g，并具有优异的收率。同样，催化剂的载量可以以适中的产率降低到1.0mol％，并且该反应提供了温和且容易的合成β-二取代的羧酸的方法。
• Covalent organic framework supported Pd(II)‐catalyzed conjugate additions of arylboronic acids to α,β‐unsaturated carboxylic acids
  作者：Min Wen、Shujuan Lu、Chaogang Fan、Kai Shen、Shaohui Lin、Qinmin Pan

  DOI：10.1002/aoc.6263

  日期：2021.8

  A palladium(II)-coordinated covalent organic framework (Pd(II)@COF) was mechanochemically synthesized from [2,2′-bipyridine]-5,5′-diamine (Bpy) and 1,3,5-triformylphloroglucinol (Tp), which was demonstrated as a catalyst for conjugate addition of arylboronic acids to unreactive α,β-unsaturated carboxylic acids in aqueous media (water/acetone = 1:1). Modest to good yields were obtained for most substrates

  由[2,2'-联吡啶]-5,5'-二胺（Bpy）和1,3,5-三甲酰基间苯三酚（Tp）机械化学合成钯（II）配位的共价有机骨架（Pd（II）@COF） )，它被证明是芳基硼酸与非反应性 α,β-不饱和羧酸在水性介质 (水/丙酮 = 1:1) 中共轭加成的催化剂。大多数底物获得了中等至良好的产率，对催化剂可回收性的研究表明，多相催化剂在前 4 个循环中的产率大于 80%。这项研究拓宽了 COF 支持的催化的应用，并为 Pd(II) 催化提供了新的选择。
• Pharmaceutically active piperidine derivatives, in particular as modulators of chemokine receptor activity
  申请人：——

  公开号：US20040006081A1

  公开（公告）日：2004-01-08

  Compounds of formula (I), compositions comprising them, processes for preparing them and their use in medical therapy (for example modulating CCR5 receptor activity in a warm blooded animal).

  式(I)的化合物，包含它们的组合物，制备它们的方法以及它们在医学疗法中的使用（例如在温血动物中调节CCR5受体活性）。