3-indol-2-yl-1-methyl-pyridinium; iodide | 15432-27-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-indol-2-yl-1-methyl-pyridinium; iodide
• 英文别名: 3-Indol-2-yl-1-methyl-pyridinium; Jodid；3-(1H-Indol-2-yl)-1-methylpyridin-1-ium iodide；2-(1-methylpyridin-1-ium-3-yl)-1H-indole;iodide
• CAS: 15432-27-6
• 化学式: C₁₄H₁₃N₂*I
• 分子量: 336.175
• InChiKey: COCJDVPQTUEDOR-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.34
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  19.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-indol-2-yl-1-methyl-pyridinium; iodide 以51%的产率得到
  参考文献：
  名称：

  KOST A. N.; STUPNIKOVA T. V.; SAGITULLIN R. S.; ZEMSKIJ B. P.; SHEJNKMAN +, DOKL. AN CCCP, 1979, 244, HO 1, 103-105

  摘要：

  DOI：
• 作为产物：
  描述：

  2-吡啶-3-基-H-吲哚 、 碘甲烷 生成 3-indol-2-yl-1-methyl-pyridinium; iodide
  参考文献：
  名称：

  Preparation and Study of Tautomers Derived from 2-(2‘-Pyridyl)indole and Related Compounds

  摘要：

  Methylation of 2-(2'-pyridyl)indole provides the corresponding N-methylated salt that undergoes deprotonation with mild base to provide the tautomeric (E)-1-methyl-2-(2'-indolenylidene)-1,2-dihydropyridine, whose geometry is established through a NOE experiment. Bridging at the 3,3'-positions leads to tautomers having the opposite stereochemistry. A benzo-fused analogue exhibits similar behavior as does 2-(2'-quinolinyl)pyrrole. The importance of the connectivity to pyridine is examined by considering three possible regioisomers, only two of which show tautomeric behavior. The tautomers show strong solvatochromic dependence and good linear behavior. The indoles absorb at shorter wavelengths and are strongly emitting while the tautomers show a strong bathochromic shift and emit only weakly; the salts exhibit intermediate behavior. NMR properties are consistent with contributions from a dipolar and uncharged resonance form while MO calculations indicate that the indole is about 40 kcal/mol more stable than its tautomer.

  DOI：

  10.1021/jo980134j

文献信息

• Preparation and Study of Tautomers Derived from 2-(2‘-Pyridyl)indole and Related Compounds
  作者：Feiyue Wu、Jon Hardesty、Randolph P. Thummel

  DOI：10.1021/jo980134j

  日期：1998.6.1

  Methylation of 2-(2'-pyridyl)indole provides the corresponding N-methylated salt that undergoes deprotonation with mild base to provide the tautomeric (E)-1-methyl-2-(2'-indolenylidene)-1,2-dihydropyridine, whose geometry is established through a NOE experiment. Bridging at the 3,3'-positions leads to tautomers having the opposite stereochemistry. A benzo-fused analogue exhibits similar behavior as does 2-(2'-quinolinyl)pyrrole. The importance of the connectivity to pyridine is examined by considering three possible regioisomers, only two of which show tautomeric behavior. The tautomers show strong solvatochromic dependence and good linear behavior. The indoles absorb at shorter wavelengths and are strongly emitting while the tautomers show a strong bathochromic shift and emit only weakly; the salts exhibit intermediate behavior. NMR properties are consistent with contributions from a dipolar and uncharged resonance form while MO calculations indicate that the indole is about 40 kcal/mol more stable than its tautomer.
• KOST A. N.; STUPNIKOVA T. V.; SAGITULLIN R. S.; ZEMSKIJ B. P.; SHEJNKMAN +, DOKL. AN CCCP, 1979, 244, HO 1, 103-105
  作者：KOST A. N.、 STUPNIKOVA T. V.、 SAGITULLIN R. S.、 ZEMSKIJ B. P.、 SHEJNKMAN +

  DOI：——

  日期：——