6-chloro-α-fluoro-3-picoline N-oxide | 253686-23-6

• 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-3-picoline N-oxide
• 英文别名: 2-Chloro-5-(fluoromethyl)-1-oxidopyridin-1-ium
• CAS: 253686-23-6
• 化学式: C₆H₅ClFNO
• 分子量: 161.563
• InChiKey: AUNNMQWPZQORAI-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：

  N-苯基哌嗪 、 6-chloro-α-fluoro-3-picoline N-oxide 以 N,N-二甲基甲酰胺 为溶剂， 以44%的产率得到α-fluoro-6-(4-phenylpiperazinyl)-3-picoline N-oxide
  参考文献：
  名称：

  Lee; Choi; Choe, Journal of labelled compounds and radiopharmaceuticals, 1999, vol. 42, # SUPPL. 1, p. S99-S101

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氯-5-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 15.33h， 生成 6-chloro-α-fluoro-3-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

• Polymer-Supported Ionic Liquids: Imidazolium Salts as Catalysts for Nucleophilic Substitution Reactions Including Fluorinations
  作者：Dong Wook Kim、Dae Yoon Chi

  DOI：10.1002/anie.200352760

  日期：2004.1.16
• 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.
• 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：——