3-methyl-2-(2'-pyridyl)-indole | 951-25-7

• 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-methyl-2-(2'-pyridyl)-indole
• 英文别名: 3-methyl-2-pyridin-2-yl-indole；3-methyl-2-[2]pyridyl-indole；3-Methyl-2-[2]pyridyl-indol；1H-Indole, 3-methyl-2-(2'-pyridyl)-；3-methyl-2-pyridin-2-yl-1H-indole
• CAS: 951-25-7
• 化学式: C₁₄H₁₂N₂
• 分子量: 208.263
• InChiKey: LHYPEZZYPUJJEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 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：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-methyl-2-(2'-pyridyl)-indole 在 氢氧化钾 作用下， 以 水 、 乙腈 为溶剂， 反应 22.17h， 生成 3-Methyl-2-[1-methyl-1H-pyridin-(2Z)-ylidene]-2H-indole
  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
• 作为产物：
  描述：

  2-丙酰基吡啶 在 盐酸 、 乙醚 、 乙醇 作用下， 生成 3-methyl-2-(2'-pyridyl)-indole
  参考文献：
  名称：

  Kao, Huaxue Xuebao/Acta Chimica Sinica, 1955, vol. 21, p. 159,163

  摘要：

  DOI：

文献信息

• A Flexible Synthesis of 2,3-Disubstituted Indoles from Aminobenzyl Phosphonium Salts. A Direct Synthesis of Rutaecarpine
  作者：George A. Kraus、Haitao Guo

  DOI：10.1021/jo900718g

  日期：2009.8.7

  substituted (2-aminobenzyl)triphenylphosphonium bromides with aromatic aldehydes or α,β-unsaturated aldehydes constitutes a new synthesis of 2,3-disubstitued indoles in high yields. The adduct from 4-oxo-3,4-dihydroquinazoline-2-carbaldehyde was an advanced intermediate in the synthesis of several rutaecarpines.

  取代的（2-氨基苄基）三苯基phosph溴化物与芳族醛或α，β-不饱和醛的反应构成了高产率的2,3-二取代的吲哚的新合成。4-氧代-3,4-二氢喹唑啉-2-甲醛的加合物是几种芸苔芸香碱合成中的高级中间体。
• Metal-Free Directed C–H Borylation of Indoles at the Sterically Congested C2 Position
  作者：Chaoguo Yan、Zhuangzhi Shi、Wang Jiang、Jingyi Bai、Jiahang Lv、Yue Zhao

  DOI：10.1055/a-2126-1750

  日期：2023.11

  metal-catalyzed C–H borylation has been one of the most notable advances in synthetic chemistry and has been widely employed in the preparation of organoboron reagents. Due to economic and heavy-metal-residue concerns, there is significant interest in the development of metal-free processes to mimic metallic systems. Here, we disclose a highly efficient metal-free approach for the directed C–H borylation of C3-substituted

  在过去的几十年里，过渡金属催化的C-H硼化反应是合成化学领域最引人注目的进展之一，并被广泛应用于有机硼试剂的制备。出于经济和重金属残留的考虑，人们对开发模仿金属系统的无金属工艺产生了浓厚的兴趣。在这里，我们公开了一种高效的无金属方法，使用廉价的硼试剂 BBr 3 在空间拥挤的 C2 位上对 C3 取代的吲哚进行定向 C-H 硼基化。与使用过渡金属的传统方法相比，该实用方案提供了获得大量 C2-硼化吲哚的理想途径。通过 (-)-goniomitine 和 bazedoxifene 关键中间体的构建以及药物氟伐他汀的全合成，也显示了复杂分子合成的好处及其在药物化学中的适用性。机理实验证明了这种 C-H 硼化过程的位点选择性。
• Bidentate Ligands That Contain Pyrrole in Place of Pyridine
  作者：Feiyue Wu、Charles M. Chamchoumis、Randolph P. Thummel

  DOI：10.1021/ic990445s

  日期：2000.2.1

  A series of ligands are prepared that are analogues of benzo-fused derivatives of 2,2'-bipyridine (bpy), in which pyrrole has been substituted for a pyridine ring. These ligands include 2-(2'-pyridyl)-indole, 2-(2'-pyrrolyl)-quinoline, and pyrrolo[3,2-h]quinoline. A novel reductive cyclization approach to the latter species is presented. All these ligands react with [Ru(bpy-d(8))(2)Cl-2], undergoing cyclometalation with concurrent deprotonation, to form complexes of the type [Ru(L)(bpy-d(8))(2)](+) where L binds as a monoanionic ligand. The complexes are readily characterized by their H-1 NMR spectra. Changes in the odor potentials and the electronic absorption spectra of both the ligands and the complexes are interpreted in terms of charge delocalization on the ligand.
• Johnson, David A.; Gribble, Gordon W., Heterocycles, 1986, vol. 24, # 8, p. 2127 - 2132
  作者：Johnson, David A.、Gribble, Gordon W.

  DOI：——

  日期：——
• 3-Methyl- and 3-ethyl-2-2′-pyridylindole
  作者：Yee-Sheng Kao、Robert Robinson

  DOI：10.1039/jr9550002865

  日期：——