1-bromo-4-(3-fluoropropyl)benzene | 168104-62-9

• 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-(3-fluoropropyl)benzene
• CAS: 168104-62-9
• 化学式: C₉H₁₀BrF
• 分子量: 217.081
• InChiKey: AMXGUFLOZMLCEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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-(3-fluoropropyl)benzene 在 氢氧化钾 、 碘 、 magnesium 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 (S)-α-hydroxy-α-<4-(3-fluoropropyl)phenyl>benzeneacetic acid
  参考文献：
  名称：

  Syntheses and Biological Properties of Chiral Fluoroalkyl Quinuclidinyl Benzilates

  摘要：

  Previously, (R)-quinuclidinyl (R)-4-iodobenzilate ((R,R)-IQNB), a muscarinic receptor antagonist, has been labeled with I-123 and I-125 for use in in vitro and in vivo studies in animals and humans. We have prepared fluoroalkyl analogs of QNB, which are amenable to labeling with F-18, for potential imaging applications with positron emission tomography. The enantiomers of (fluoroalkyl)benzilic acids were prepared via an enantioselective Grignard addition reaction. Subsequent coupling of the enantiomeric (fluoroalkyl)benzilic acid with a selected enantiomer of quinuclidinol provides fluorinated analogs of QNB with known stereochemistry at each of the stereogenic centers. These compounds exhibit different affinities for the muscarinic receptor tissue subtypes in vitro. (R,R)-4-(Fluoromethyl)-QNB, (R,R)-IQNB, and (R,R)-4-(fluoroethyl)-QNB exhibit selectivity for the M1 subtype, and (R,S)-4-(fluoromethyl)-QNB exhibits selectivity for the M2 subtype.

  DOI：

  10.1021/jm00010a016
• 作为产物：
  描述：

  4-溴苯丙醇 在 potassium fluoride 、 N-苯基双(三氟甲烷磺酰)亚胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以60%的产率得到1-bromo-4-(3-fluoropropyl)benzene
  参考文献：
  名称：

  以 KF 为氟源的醇直接脱氧氟化

  摘要：

  本报告描述了一种以 KF 作为氟源通过原位生成高活性 CF 3 SO 2 F 的醇脱氧氟化的方法。包括卤素、硝基、酮、酯、烯烃和炔烃在内的多种官能团具有良好的耐受性。温和的条件、短的反应时间和广泛的底物范围使该方法成为构建 C-F 键的绝佳选择。

  DOI：

  10.1021/acs.joc.2c00388

文献信息

• Divergent, Stereospecific Mono‐ and Difluoromethylation of Boronic Esters
  作者：Valerio Fasano、Nils Winter、Adam Noble、Varinder K. Aggarwal

  DOI：10.1002/anie.202002246

  日期：2020.5.25

  CHF2 groups, they are mainly limited to radical reactions, which are invariably racemic. Herein, we report the divergent, stereospecific reaction of fluoroiodomethyllithium with boronic esters to give α-fluoro-boronic esters. These unique intermediates can be readily transformed into the corresponding mono- or difluoromethylated compounds through proto- or fluorodeboronation, respectively. The use of

  将氟掺入农用化学品和药物中以改善其生物学特性引起了相当大的兴趣。尽管已经报道了许多用于安装CH 2 F和CHF 2基团的方法，但它们主要限于自由基反应，而自由基反应总是消旋的。在本文中，我们报道了氟碘甲基锂与硼酸酯的发散立体定向反应，从而生成α-氟硼酸酯。这些独特的中间体可以分别通过原脱氟或氟脱硼容易地转化为相应的单氟甲基化或二氟甲基化的化合物。使用高度不稳定的氟代碘代甲基锂是实现快速1，2-迁移而不是碳负离子竞争分解的关键。DFT计算为实验结果提供了依据并提供了支持。
• Cu-catalyzed intramolecular aryl-etherification reactions of alkoxyl alkynes with diaryliodonium salts via cleavage of a stable C–O bond
  作者：Jing Chen、Chao Chen、Junjie Chen、Guohua Wang、Hongmei Qu

  DOI：10.1039/c4cc08363f

  日期：——

  A novel Cu-catalyzed intramolecular aryl-etherification reaction of alkoxyl alkynes with diaryliodonium salts is realized. The reactions proceed smoothly to produce valuable oxo-heterocycles with readily available linear starting materials via cleavage of a stable C-O bond.

  实现了一种新型的铜催化的烷氧基炔烃与二芳基碘鎓盐的分子内芳基醚化反应。反应平稳进行，通过裂解稳定的CO键，生成具有容易获得的线性起始原料的有价值的氧杂环。
• Imaging Agents for Detecting Neurological Dysfunction
  申请人：Szardenings Anna Katrin

  公开号：US20120302755A1

  公开（公告）日：2012-11-29

  Disclosed here in are compounds and methods of diagnosing Alzheimer's Disease or a predisposition thereto in a mammal, the method comprising administering to the mammal a diagnostically effective amount of a radiolabeled compound, wherein the compound is selected from the group consisting of radiolabeled carbazoles and derivatives thereof and triazoles derivatives, allowing the compound to distribute into the brain tissue, and imaging the brain tissue, wherein an increase in binding of the compound to the brain tissue compared to a normal control level of binding indicates that the mammal is suffering from or is at risk of developing Alzheimer's Disease.

  本文公开了一种诊断哺乳动物阿尔茨海默病或其易感性的化合物和方法，其中该方法包括向哺乳动物施加诊断有效量的放射性标记化合物，所述化合物选自放射性标记的咔唑衍生物和其衍生物以及三唑衍生物组成的群体，允许该化合物分布到脑组织中，并成像脑组织，其中与正常控制结合水平相比，化合物对脑组织的结合增加表明哺乳动物正在患有或有发展阿尔茨海默病的风险。
• Imaging agents for detecting neurological dysfunction
  申请人：Eli Lilly and Company

  公开号：US20150030540A1

  公开（公告）日：2015-01-29

  Disclosed here in are compounds and methods of diagnosing Alzheimer's Disease or a predisposition thereto in a mammal, the method comprising administering to the mammal a diagnostically effective amount of a radiolabeled compound, wherein the compound is selected from the group consisting of radiolabeled carbazoles and derivatives thereof and triazoles derivatives, allowing the compound to distribute into the brain tissue, and imaging the brain tissue, wherein an increase in binding of the compound to the brain tissue compared to a normal control level of binding indicates that the mammal is suffering from or is at risk of developing Alzheimer's Disease.

  本文中披露了在哺乳动物中诊断阿尔茨海默病或其易感性的化合物和方法，该方法包括向哺乳动物施用诊断有效量的放射性标记化合物，所述化合物选自放射性标记的咔唑衍生物和其衍生物以及三唑衍生物的群组，使化合物分布到脑组织中，并成像脑组织，其中化合物与脑组织的结合增加，与正常对照水平的结合相比，表明哺乳动物正在患有或有发展阿尔茨海默病的风险。
• OXAZINE MONOACYLGLYCEROL LIPASE (MAGL) INHIBITORS
  申请人：F. Hoffmann-La Roche AG

  公开号：EP3768684A1

  公开（公告）日：2021-01-27