6-chloro-α-fluoro-2-picoline N-oxide | 253686-20-3

• 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: 6-chloro-α-fluoro-2-picoline N-oxide
• 英文别名: 2-Chloro-6-(fluoromethyl)-1-oxidopyridin-1-ium
• CAS: 253686-20-3
• 化学式: C₆H₅ClFNO
• 分子量: 161.563
• InChiKey: DCAMWQIGZSVILX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 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：
  25.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-chloro-α-fluoro-2-picoline N-oxide 在 三乙胺 、 三氯化磷 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 α-fluoro-6-(4-phenylpiperazinyl)-2-picoline
  参考文献：
  名称：

  An Efficient Synthesis of (Fluoromethyl)pyridylamines for Labeling with Fluorine-18

  摘要：

  We have described a two-step method for the preparation of (fluoromethyl)pyridyl-substituted amines. The sequence involves fluoride ion displacement of methanesulfonates (mesylates) of 6-chloro-alpha-hydroxy-2- and -3-picolines, followed by arylation of the amine by chloropicoline. We have called this sequence fluorination-N-arylation. 1-Phenylpiperazine has been used as a model amine. Two key precursors for this sequence are the mesylates of 6-chloro-alpha-hydroxy-2- and -3-picolines. The former was synthesized in four steps from 6-chloro-2-picoline in 78% yield and the latter in three Steps from 6-chloronicotinic acid in 53% yield. This fluorination-N-arylation sequence is sufficiently rapid and efficient for the preparation of a variety of aryl-substituted amine compounds labeled with the short half-life (t(1/2) = 110 min) positron-emitting radionuclide fluorine-18.

  DOI：

  10.1021/jo990994f
• 作为产物：
  描述：

  6-氯-2-羟甲基吡啶 在 四丁基氟化铵 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 氯仿 、 乙腈 为溶剂， 反应 16.5h， 生成 6-chloro-α-fluoro-2-picoline N-oxide
  参考文献：
  名称：

  An Efficient Synthesis of (Fluoromethyl)pyridylamines for Labeling with Fluorine-18

  摘要：

  We have described a two-step method for the preparation of (fluoromethyl)pyridyl-substituted amines. The sequence involves fluoride ion displacement of methanesulfonates (mesylates) of 6-chloro-alpha-hydroxy-2- and -3-picolines, followed by arylation of the amine by chloropicoline. We have called this sequence fluorination-N-arylation. 1-Phenylpiperazine has been used as a model amine. Two key precursors for this sequence are the mesylates of 6-chloro-alpha-hydroxy-2- and -3-picolines. The former was synthesized in four steps from 6-chloro-2-picoline in 78% yield and the latter in three Steps from 6-chloronicotinic acid in 53% yield. This fluorination-N-arylation sequence is sufficiently rapid and efficient for the preparation of a variety of aryl-substituted amine compounds labeled with the short half-life (t(1/2) = 110 min) positron-emitting radionuclide fluorine-18.

  DOI：

  10.1021/jo990994f

文献信息

• Synthesis and evaluation of fluorine-substituted 1H-pyrrolo[2,3-b]pyridine derivatives for dopamine D4 receptor imaging
  作者：Seung-Jun Oh、Kyo Chul Lee、Sang-Yoon Lee、Eun Kyoung Ryu、Hideo Saji、Yearn Seong Choe、Dae Yoon Chi、Sang Eun Kim、Jeewoo Lee、Byung-Tae Kim

  DOI：10.1016/j.bmc.2004.08.011

  日期：2004.11

  o[2,3-b]pyridine (L-750,667) and evaluated as potential dopamine D(4) receptor imaging agents by positron emission tomography (PET). Binding affinities of these ligands for the dopamine D(2), D(3), and D(4) receptor subtypes were measured in vitro. Most ligands showed high and selective binding for the D(4) receptor. Ligand 7 had high affinity for the D(4) receptor, whereas ligands 1, 2, and 6 showed

  基于铅配体3-[[[4-（4-碘苯基）哌嗪-1-基]-甲基] -1H-吡咯[2]合成了七个氟取代的1H-吡咯并[2,3-b]吡啶衍生物，3-b]吡啶（L-750,667）并通过正电子发射断层扫描（PET）评估为潜在的多巴胺D（4）受体成像剂。这些配体对多巴胺D（2），D（3）和D（4）受体亚型的结合亲和力在体外进行了测量。大多数配体显示出对D（4）受体的高选择性结合。配体7对D（4）受体具有高亲和力，而配体1、2和6对D（4）受体具有高选择性。计算该系列中的配体的LogP值，并且配体6具有最低的亲脂性。（18）F标记的配体7在小鼠中表现出均匀的区域脑分布和快速冲洗，这可能是由于非特异性结合所致。
• Lee; Choi; Choe, Journal of labelled compounds and radiopharmaceuticals, 1999, vol. 42, # SUPPL. 1, p. S99-S101
  作者：Lee、Choi、Choe、Kim、Chi

  DOI：——

  日期：——
• An Efficient Synthesis of (Fluoromethyl)pyridylamines for Labeling with Fluorine-18
  作者：Kyo Chul Lee、Dae Yoon Chi

  DOI：10.1021/jo990994f

  日期：1999.11.1

  We have described a two-step method for the preparation of (fluoromethyl)pyridyl-substituted amines. The sequence involves fluoride ion displacement of methanesulfonates (mesylates) of 6-chloro-alpha-hydroxy-2- and -3-picolines, followed by arylation of the amine by chloropicoline. We have called this sequence fluorination-N-arylation. 1-Phenylpiperazine has been used as a model amine. Two key precursors for this sequence are the mesylates of 6-chloro-alpha-hydroxy-2- and -3-picolines. The former was synthesized in four steps from 6-chloro-2-picoline in 78% yield and the latter in three Steps from 6-chloronicotinic acid in 53% yield. This fluorination-N-arylation sequence is sufficiently rapid and efficient for the preparation of a variety of aryl-substituted amine compounds labeled with the short half-life (t(1/2) = 110 min) positron-emitting radionuclide fluorine-18.