2,5-Bis(5-chloro-3-pyridinyl)pyrrole

• 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: 2,5-Bis(5-chloro-3-pyridinyl)pyrrole
• 英文别名: 3-chloro-5-[5-(5-chloropyridin-3-yl)-1H-pyrrol-2-yl]pyridine
• 化学式: C₁₄H₉Cl₂N₃
• 分子量: 290.152
• InChiKey: ACLHBTAIAGJMAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,5-二氯吡啶 、 吡咯 在 4,4'-联吡啶 作用下， 以8%的产率得到3-Chloro-5-(1H-pyrrol-3-yl)-pyridine
  参考文献：
  名称：

  Delocalized Nitrogen Carbanions in SRN1 Reactions

  摘要：

  S(RN)1 reactions can be performed with nitrogen carbanions as nucleophiles, and generally the reaction leads to a mixture of isomers. In the case of the pyrrolyl anion, position 2 is about four times more reactive than position 3. When the ortho positions of pyrrole are substituted by alkyl groups, the reactivity of position 2 increases while that of position 3 decreases. With tert-butyl groups as the substituents, no reaction at position 2 is observed. With the indolyl anion as the nucleophiIe, no substitution at position 2 or at the phenyl ring is observed, and only one product corresponding to monosubstitution at position 3 is obtained. Imidazolyl anions react preferentially at position 4 (5), and substitution of position 2 by a methyl group makes the coupling regioselective.

  DOI：

  10.1021/jo00129a048

文献信息

• Delocalized Nitrogen Carbanions in SRN1 Reactions
  作者：M. Chahma、C. Combellas、A. Thiebault

  DOI：10.1021/jo00129a048

  日期：1995.12

  S(RN)1 reactions can be performed with nitrogen carbanions as nucleophiles, and generally the reaction leads to a mixture of isomers. In the case of the pyrrolyl anion, position 2 is about four times more reactive than position 3. When the ortho positions of pyrrole are substituted by alkyl groups, the reactivity of position 2 increases while that of position 3 decreases. With tert-butyl groups as the substituents, no reaction at position 2 is observed. With the indolyl anion as the nucleophiIe, no substitution at position 2 or at the phenyl ring is observed, and only one product corresponding to monosubstitution at position 3 is obtained. Imidazolyl anions react preferentially at position 4 (5), and substitution of position 2 by a methyl group makes the coupling regioselective.