α-fluoro-6-(4-phenylpiperazinyl)-3-picoline N-oxide | 253686-27-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: α-fluoro-6-(4-phenylpiperazinyl)-3-picoline N-oxide
• 英文别名: 1-[5-(Fluoromethyl)-1-oxidopyridin-1-ium-2-yl]-4-phenylpiperazine
• CAS: 253686-27-0
• 化学式: C₁₆H₁₈FN₃O
• 分子量: 287.337
• InChiKey: KLDRCVXZARSLGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  31.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  α-fluoro-6-(4-phenylpiperazinyl)-3-picoline N-oxide 在 三氯化磷 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以99%的产率得到α-fluoro-6-(4-phenylpiperazinyl)-3-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：

  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 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 0.5h， 生成 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：

文献信息

• 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：——