1-bromo-4-(4-fluorobenzyl)benzene | 17100-44-6

• 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: 1-bromo-4-(4-fluorobenzyl)benzene
• 英文别名: 1-bromo-4-[(4-fluorophenyl)methyl]benzene
• CAS: 17100-44-6
• 化学式: C₁₃H₁₀BrF
• 分子量: 265.125
• InChiKey: INGGMFGQLHYMPX-UHFFFAOYSA-N

物化性质

• 沸点：
  320.0±22.0 °C(Predicted)
• 密度：
  1.401±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-bromo-4-(4-fluorobenzyl)benzene 在 偶氮二异丁腈 、 氧气 作用下， 以 乙腈 为溶剂， 反应 32.0h， 以62%的产率得到四溴-4'-氟苯二甲酮
  参考文献：
  名称：

  AIBN在存在双氧的情况下引发了苄基sp 3 C H和C C键的官能化

  摘要：

  通过AIBN / O 2催化剂体系实现了sp 3 C H键的官能化和C C键的裂解，在温和的反应条件下提供了一系列的二苯甲酮。机理研究表明，过氧化物中间体参与了这一转变，在二苯基甲烷的情况下，sp 3 C C键通过过氧化物重排而断裂，这可能提供了一种断裂相对较强的C C键并被应用的新方法。更一般的C C键活化。

  DOI：

  10.1016/j.tetlet.2020.152806
• 作为产物：
  描述：

  4-bromo-4'-fluorodiphenylmethanol 在 三乙基硅烷 作用下， 以 三氟乙酸 为溶剂， 反应 1.0h， 以3.9 g的产率得到1-bromo-4-(4-fluorobenzyl)benzene
  参考文献：
  名称：

  Synthesis and biological evaluation of new 4-arylpiperidines and 4-aryl-4-piperidinols: dual Na+ and Ca2+ channel blockers with reduced affinity for dopamine D2 receptors

  摘要：

  A series of novel 4-arylpiperidines and 4-aryl-4-piperidinols (2a-f, 3a f and 4a-f) wits synthesized and evaluated for blocking effects on both neuronal Na+ and T-type Ca2+ channels and binding affinity for dopamine D-2 receptors. Most or the compounds blockaded both ion channels with potency greater than or equal to flunarizine Ia which was adopted as a reference standard. In addition, these compounds had significantly reduced affinity for dopamine D-2 receptors which is common in this class of structure. Compounds 2a-f, 3a-f and 4a-f exhibited potent anticonvulsant effects following systemic (ip) administration on audiogenic seizures in DBA/2 mice, indicating their excellent brain permeability. The neuroprotective activity of 2a, 3a and 4a was also assessed in a transient middle cerebral artery Occlusion (MCAO) model. These Compounds significantly reduced neuronal damage without affecting ischemic hyperthemia, while flunarizine Ia produced only minor reductions. In particular. 4a had 1.7-fold the potency in this MCAO model but only 1/20 the affinity for dopamine D-2 receptors of 1a. The Superposition of 2a, 3a and 4a on the basis of analyses of systematic conformation and similar structure has revealed that the cinnamyl, phenacyl and phenoxy-propanol groups are likely to be structurally and biologically equivalent. Moreover, the Superposition of 2a and 2f shows that diphenyl ether and biphenyl groups occupy a similar space, suggesting that both groups act as a bioisostere for the blockade of ion channels: however, this is not the case for dopamine D-2 receptors since only biphenyl Compounds such as 2f had high affinity similar to flunarizine Ia. Compound 4a (SUN N5030) has a good pharmacological profile and may be Useful in the alleviation and treatment or ischemic diseases. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00288-7

文献信息

• Metal-Free C–O Bond Functionalization: Catalytic Intramolecular and Intermolecular Benzylation of Arenes
  作者：Luis Bering、Kirujan Jeyakumar、Andrey P. Antonchick

  DOI：10.1021/acs.orglett.8b01495

  日期：2018.7.6

  conditions enabled a catalytic and metal-free Friedel–Crafts alkylation reaction with benzylic alcohols, producing water as the stoichiometric byproduct. A comprehensive scope (>50 examples) for both approaches and application in drug synthesis were demonstrated. Mechanistic studies suggest a Lewis acid-based mechanism for the metal-free Friedel–Crafts reaction.

  描述了使用硝鎓盐作为催化剂的苄基苯基醚的无金属催化的分子内重排。优化的反应条件使苄基醇能够进行无金属催化的Friedel-Crafts烷基化反应，从而产生水作为化学计量副产物。展示了方法和在药物合成中的应用的综合范围（> 50个示例）。机理研究表明，路易斯酸基机理可用于无金属的Friedel-Crafts反应。
• Pyrrolidine modulators of chemokine receptor activity
  申请人：Merck & Co., Inc.

  公开号：US06248755B1

  公开（公告）日：2001-06-19

  The present invention is directed to pyrrolidine compounds of the formula I: (wherein R1, R2, R3, R4, R5, R6, R14 and n are defined herein) which are useful as modulators of chemokine receptor activity. In particular, these compounds are useful as modulators of the chemokine receptors CCR-5 and/or CCR-3.

  本发明涉及式I的吡咯烷化合物： （其中R1，R2，R3，R4，R5，R6，R14和n的定义如本文中）这些化合物可用作调节化学趋化因子受体活性的调节剂。特别是，这些化合物可用作调节CCR-5和/或CCR-3的化学趋化因子受体的调节剂。
• 5-HYDROXYPYRIMIDINE-4-CARBOXAMIDE COMPOUND
  申请人：Kuribayashi Takeshi

  公开号：US20110112103A1

  公开（公告）日：2011-05-12

  The present invention provides compounds which promote erythropoietin production. Compounds represented by the following general formula (1) or pharmacologically acceptable salts thereof are provided: [wherein, R 1 represents a group —X-Q 1 , X-Q 1 -Y-Q 2 or X-Q 1 -Y-Q 2 -Z-Q 3 , X represents a single bond, —CH 2 — or the like, Q 1 represents a monocyclic or bicyclic heterocyclic group which may have substituent(s), Y represents a single bond, —CH 2 —, or the like, Q 2 represents a monocyclic or bicyclic hydrocarbon ring group which may have substituent(s) or a monocyclic or bicyclic heterocyclic group which may have substituent(s), Z represents a single bond, —CR 11 R 12 — or the like, R 11 and R 12 each independently represents a hydrogen atom, a halogen atom or the like, Q 3 represents a phenyl group which may have substituent(s), a C 3 -C 7 cycloalkyl group which may have substituent(s), a C 3 -C 7 cycloalkenyl group which may have substituent(s) or a monocyclic or bicyclic heterocyclic group which may have substituent(s), R 2 represents a C 1 -C 3 alkyl group or the like, and R 3 represents a hydrogen atom or a methyl group].

  本发明提供促进促红细胞生成素产生的化合物。提供以下一般式（1）表示的化合物或其药理学上可接受的盐： [其中，R 1 表示一个基团-X-Q 1 ，X-Q 1 -Y-Q 2 或X-Q 1 -Y-Q 2 -Z-Q 3 ，X表示一个单键，-CH 2 -或类似物，Q 1 表示可能具有取代基的单环或双环杂环基团，Y表示一个单键，-CH 2 -或类似物，Q 2 表示可能具有取代基的单环或双环碳氢环基团或可能具有取代基的单环或双环杂环基团，Z表示一个单键，-CR 11 R 12 -或类似物，R 11 和R 12 各自独立地表示氢原子、卤素原子或类似物，Q 3 表示可能具有取代基的苯基团，可能具有取代基的C 3 -C 7 环烷基团，可能具有取代基的C 3 -C 7 环烯基团或可能具有取代基的单环或双环杂环基团，R 2 表示C 1 -C 3 烷基团或类似物，R 3 表示氢原子或甲基基团]。
• Alumina grafted SBA-15 sustainable bifunctional catalysts for direct cross-coupling of benzylic alcohols to diarylmethanes
  作者：Chandran Rajendran、Govindaswamy Satishkumar、Charlotte Lang、Eric M. Gaigneaux

  DOI：10.1039/d0cy00471e

  日期：——

  desorption (TPD) and pyridine-transmission-FTIR spectroscopy techniques to confirm the existence of Brønsted acid and Lewis acid–base bifunctionalities. Through various control experiments, it is verified that Brønsted acid sites activate the benzyl alcohol and Lewis base sites interact with phenylboronic acid concurrently to accomplish the coupling reaction. In the recyclability study, 4wt%AlSBA-15 preserves

  具有布朗斯台德酸和路易斯酸碱双官能度的AlSBA-15催化剂可催化苄醇直接芳基化为二芳基甲烷，并通过C-O键活化获得85％的产率。通过采用简单有效的合成后金属注入途径，合成了2wt％和4wt％AlSBA-15催化剂。用XRD，N 2吸附和解吸，27 Al MAS NMR，XPS，HR-TEM，NH 3和CO 2表征合成的催化剂。程序升温脱附（TPD）和吡啶传递FTIR光谱技术确定了布朗斯台德酸和路易斯酸碱双官能团的存在。通过各种控制实验，证实布朗斯台德酸位点激活苯甲醇，路易斯碱位点同时与苯硼酸相互作用，完成偶联反应。在可回收性研究中，4wt％AlSBA-15最多可保留5个循环的活性和稳定性。与均相催化剂不同，4wt％AlSBA-15催化剂不需要添加剂，较长的反应时间和昂贵的金属。
• Unsymmetrical Diarylmethanes by Ferroceniumboronic Acid Catalyzed Direct Friedel–Crafts Reactions with Deactivated Benzylic Alcohols: Enhanced Reactivity due to Ion-Pairing Effects
  作者：Xiaobin Mo、Joshua Yakiwchuk、Julien Dansereau、J. Adam McCubbin、Dennis G. Hall

  DOI：10.1021/jacs.5b05076

  日期：2015.8.5

  displays a broader scope compared to previously reported catalysts for similar Friedel-Crafts reactions of benzylic alcohols, including other boronic acids such as 2,3,4,5-tetrafluorophenylboronic acid. The efficacy of the new boronic acid catalyst was confirmed by its ability to activate primary benzylic alcohols functionalized with destabilizing electron-withdrawing groups like halides, carboxyesters

  开发用于未活化芳烃的 Friedel-Crafts 烷基化的通用和更原子经济的催化过程是制药和商品化学品生产的一个重要目标。二茂铁硼酸六氟锑酸盐 (1) 被认为是一种优异的耐空气和耐湿催化剂，可用于各种轻度活化和中性芳烃与稳定且容易获得的伯醇和仲苯甲醇的直接弗瑞德-克来福特烷基化反应。与使用具有毒性的苄基卤化物的经典金属催化烷基化相比，该方法采用异常温和的条件以高产率提供各种不对称二芳基甲烷和其他 1,1-二芳基烷烃产品，具有良好到高的区域选择性。最优方法，与之前报道的用于苯甲醇（包括其他硼酸（如 2,3,4,5-四氟苯基硼酸）的类似 Friedel-Crafts 反应）的催化剂相比，在六氟异丙醇中使用长期稳定的二茂铁硼酸盐 1 作为助溶剂显示出更广泛的范围。新型硼酸催化剂的功效通过其活化被去稳定吸电子基团（如卤化物、羧酸酯和硝基取代基）官能化的伯苄醇的能力得到证实。芳烃苄基化在高达 1 M