2-dibromomethyl-6-fluoropyridine | 1243694-61-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-dibromomethyl-6-fluoropyridine
• 英文别名: 2-fluoro-6-(dibromomethyl)pyridine；2-(Dibromomethyl)-6-fluoropyridine
• CAS: 1243694-61-2
• 化学式: C₆H₄Br₂FN
• 分子量: 268.911
• InChiKey: AXUWCJVTVYLXKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-dibromomethyl-6-fluoropyridine 在 silver nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 3.0h， 以60%的产率得到6-氟-2-吡啶甲醛
  参考文献：
  名称：

  Separation of Geometric Isomers of a Dicopper Complex by Using a ¹⁹F-Labeled Ligand: Dynamics, Structures, and DFT Calculations

  摘要：

  Introducing a fluorine group on two pyridines of the HLCH3 ligand (2,6-bis[(bis(2-pyridylmethyl)amino)methyl]-4-methylphenol) allows the separation of two geometric isomers after complexation by two copper(II) ions. Methods for isolating the isomers (1(meso) and 1(rac)) as a mu-phenoxo, mu-hydroxo dicopper(II) complex as a crystalline product have been developed. Both isomers (1(meso) and 1(rac)) have been characterized by X-ray crystallography and F-19 NMR. The isomerism is determined by the disposition of the fluorine atoms with respect to the plane containing the Cu2O2 core. Density functional theory calculations using different functionals were performed to provide additional support for the existence of these two forms. Dissolution of 1(meso) in acetone or acetonitrile causes its spontaneous isomerization into the 1(rac) form at room temperature. Combined experimental studies (UV-vis, F-19 NMR) and theoretical calculations support this process. Paramagnetic F-19 NMR appears as a unique and powerful probe for distinguishing the two isomers and supplying direct evidence of this isomerization process in solution.

  DOI：

  10.1021/ic1006567
• 作为产物：
  描述：

  2-氟-6-甲基吡啶 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 54.0h， 以75%的产率得到2-dibromomethyl-6-fluoropyridine
  参考文献：
  名称：

  Separation of Geometric Isomers of a Dicopper Complex by Using a ¹⁹F-Labeled Ligand: Dynamics, Structures, and DFT Calculations

  摘要：

  Introducing a fluorine group on two pyridines of the HLCH3 ligand (2,6-bis[(bis(2-pyridylmethyl)amino)methyl]-4-methylphenol) allows the separation of two geometric isomers after complexation by two copper(II) ions. Methods for isolating the isomers (1(meso) and 1(rac)) as a mu-phenoxo, mu-hydroxo dicopper(II) complex as a crystalline product have been developed. Both isomers (1(meso) and 1(rac)) have been characterized by X-ray crystallography and F-19 NMR. The isomerism is determined by the disposition of the fluorine atoms with respect to the plane containing the Cu2O2 core. Density functional theory calculations using different functionals were performed to provide additional support for the existence of these two forms. Dissolution of 1(meso) in acetone or acetonitrile causes its spontaneous isomerization into the 1(rac) form at room temperature. Combined experimental studies (UV-vis, F-19 NMR) and theoretical calculations support this process. Paramagnetic F-19 NMR appears as a unique and powerful probe for distinguishing the two isomers and supplying direct evidence of this isomerization process in solution.

  DOI：

  10.1021/ic1006567

文献信息

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  作者：Gui-Chao Kuang、Heather A. Michaels、J. Tyler Simmons、Ronald J. Clark、Lei Zhu

  DOI：10.1021/jo101305m

  日期：2010.10.1

  complex of T6 were characterized by X-ray crystallography. The structure of [Cu(T1)2(H2O)2](ClO4)2 reveals the interesting synergistic effect of hydrogen bonding, π−π stacking interactions, and metal coordination in forming a one-dimensional supramolecular construct in the solid state. The tetradentate coordination mode of T6 may be incorporated into designs of new molecule sensors and organometallic

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• Targeting cyclic nucleotide phosphodiesterase 5 (PDE5) in brain: Toward the development of a PET radioligand labeled with fluorine-18
  作者：Barbara Wenzel、Jianrong Liu、Sladjana Dukic-Stefanovic、Winnie Deuther-Conrad、Rodrigo Teodoro、Friedrich-Alexander Ludwig、Jean-Michel Chezal、Emmanuel Moreau、Peter Brust、Aurelie Maisonial-Besset

  DOI：10.1016/j.bioorg.2019.01.037

  日期：2019.5

  3-fluoroazetidine moiety, was further radiolabeled by aliphatic nucleophilic substitution of two different leaving groups (nosylate and tosylate) using [18F]fluoride. The use of the nosylate precursor and tetra-n-butyl ammonium [18F]fluoride ([18F]TBAF) in 3-methyl-3-pentanol combined with the addition of a small amount of water proved to be the best radiolabeling conditions achieving a RCY of 4.9 ± 1

  为了开发一种通过正电子发射断层扫描（PET）对大脑中的环状核苷酸磷酸二酯酶5（PDE5）成像的特定放射性配体，在喹啉核心的基础上合成了七种新的氟化抑制剂（3-9）。在体外确定了对PDE5的抑制活性以及一组其他PDE，并选择了两种衍生物进行IC50值测定。含有3-氟氮杂环丁烷部分的最有前途的化合物7（对于PDE5A，IC50 = 5.92 nM）通过使用[18F]氟化物的两个不同的离去基团（壬酸酯和甲苯磺酸酯）的脂族亲核取代进一步进行了放射性标记。在3-甲基-3-戊醇中配合使用甲磺酸酯前体和四正丁基[18F]氟化铵（[18F] TBAF），并加入少量水被证明是最佳的放射性标记条件，可实现自动化程序中的RCY为4.9±1.5％。进行了体外和体内的初步生物学研究，以表征这种新的PDE5放射性配体。在小鼠中对[18F] 7的代谢研究表明，在大脑中已检测到放射性代谢产物的形成，从而使代谢迅速降解。
• Fluoropyridinylmethyl cyclopropanecarboxylate insecticides
  申请人：FMC Corporation

  公开号：US04701464A1

  公开（公告）日：1987-10-20

  Insecticidal compounds of the formula ##STR1## formulations thereof, their use for control of foliar or soil-borne insects, their method of preparation and certain novel intermediates for their preparation are disclosed and exemplified.

  本发明公开了化学式为##STR1##的杀虫化合物及其配方，用于控制叶面或土壤中的昆虫，其制备方法以及用于制备它们的某些新型中间体。
• FLUOROPYRIDINYLMETHYL CYCLOPROPANECARBOXYLATE INSECTICIDES AND INTERMEDIATES
  申请人：FMC Corporation

  公开号：EP0176594A1

  公开（公告）日：1986-04-09
• US4701464A
  申请人：——

  公开号：US4701464A

  公开（公告）日：1987-10-20