3,3'-Dichloro-2,2'-difluoro-[4,4']bipyridinyl

• 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: 3,3'-Dichloro-2,2'-difluoro-[4,4']bipyridinyl
• 英文别名: 3-Chloro-4-(3-chloro-2-fluoropyridin-4-yl)-2-fluoropyridine；3-chloro-4-(3-chloro-2-fluoropyridin-4-yl)-2-fluoropyridine
• 化学式: C₁₀H₄Cl₂F₂N₂
• 分子量: 261.058
• InChiKey: BAROGCXAUHCCDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-氯-2-氟吡啶 在 Bu₂(TMP)MgLi 、 碘 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以42%的产率得到3,3'-Dichloro-2,2'-difluoro-[4,4']bipyridinyl
  参考文献：
  名称：

  Deprotonation of chloropyridines using lithium magnesates

  摘要：

  4-Chloropyridine was deprotonated on treatment with 1/3 equiv of the highly coordinated magnesate Bu-3(TMP)MgLi2 in THF at -10degreesC, as evidenced by trapping with I-2. The use of Bu(TMP)(2)MgLi in Et2O allowed the reaction of 2-chloropyridine, giving the 3-functionalized derivative as the main product. Mixtures of 3- and 4-functionalized derivatives were obtained when 2,6-dichloropyridine was involved in the reaction. Performing the reaction on 3-chloropyridine with lithium magnesates in THF, either the 4,4'-dimer or the 4-iodo derivative was formed after quenching by I-2, the former using 1/3equiv of Bu-2(TMP)MgLi and the latter using 1 equiv of (TMP)(3)MgLi. Similar results were observed with 3,5-dichloropyridine, 2,5-dichloropyridine and 3-chloro-2-fluoropyridine. 1,2-Migration of the lithium arylmagnesate formed by deprotonation was proposed to justify the dimers formation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.08.151

文献信息

• Deprotonation of chloropyridines using lithium magnesates
  作者：Haçan Awad、Florence Mongin、François Trécourt、Guy Quéguiner、Francis Marsais

  DOI：10.1016/j.tetlet.2004.08.151

  日期：2004.10

  4-Chloropyridine was deprotonated on treatment with 1/3 equiv of the highly coordinated magnesate Bu-3(TMP)MgLi2 in THF at -10degreesC, as evidenced by trapping with I-2. The use of Bu(TMP)(2)MgLi in Et2O allowed the reaction of 2-chloropyridine, giving the 3-functionalized derivative as the main product. Mixtures of 3- and 4-functionalized derivatives were obtained when 2,6-dichloropyridine was involved in the reaction. Performing the reaction on 3-chloropyridine with lithium magnesates in THF, either the 4,4'-dimer or the 4-iodo derivative was formed after quenching by I-2, the former using 1/3equiv of Bu-2(TMP)MgLi and the latter using 1 equiv of (TMP)(3)MgLi. Similar results were observed with 3,5-dichloropyridine, 2,5-dichloropyridine and 3-chloro-2-fluoropyridine. 1,2-Migration of the lithium arylmagnesate formed by deprotonation was proposed to justify the dimers formation. (C) 2004 Elsevier Ltd. All rights reserved.