N-Tolyl-2,3,4,5-tetramethylpyrrole | 86803-68-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: N-Tolyl-2,3,4,5-tetramethylpyrrole
• 英文别名: 2,3,4,5-tetramethyl-1-(4-methylphenyl)pyrrole
• CAS: 86803-68-1
• 化学式: C₁₅H₁₉N
• 分子量: 213.323
• InChiKey: ZIMVCJMEZAMNNQ-UHFFFAOYSA-N

物化性质

• 沸点：
  339.6±21.0 °C(Predicted)
• 密度：
  0.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  4.93
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  tetramethylcyclobutadiene*aluminum trichloride 、 N-亚磺酰对甲苯胺 生成 N-Tolyl-2,3,4,5-tetramethylpyrrole
  参考文献：
  名称：

  Benzvalene- and Dewar benzene-type sulfinamides

  摘要：

  DOI：

  10.1021/jo00171a024

文献信息

• Oxidative nitrene transfer from azides to alkynes <i>via</i> Ti(<scp>ii</scp>)/Ti(<scp>iv</scp>) redox catalysis: formal [2+2+1] synthesis of pyrroles
  作者：Adam J. Pearce、Xin Yi See、Ian A. Tonks

  DOI：10.1039/c8cc02623h

  日期：——

  Catalytic oxidative nitrene transfer from azides with the early transition metals is rare, and has not been observed without the support of redox noninnocent spectator ligands.

  从早期过渡金属中的叠氮化物进行催化氧化亚胺转移是罕见的，并且在没有氧化还原非无辜旁观配体的支持下尚未观察到。
• Electrochemical Oxidation and EPR Spectroscopy of Radical Cations of N-Substituted 2,3,4,5-Tetramethylpyrroles.
  作者：Robert Klusák、Pavel Kubáček、Domenico C. Cupertino、Lage Pettersson、Louisa Barré、Ole Hammerich、Inger Søtofte、Bengt Långström

  DOI：10.3891/acta.chem.scand.52-0399

  日期：——

  Electrochemical oxidation of 19 N-substituted 2,3,4,5-tetramethylpyrroles has been studied in acetonitrile and dichloromethane by means of slow cyclic voltammetry and coulometry. The first oxidation consumes one electron and occurs within the potential range 0.60-0.94 V in acetonitrile and 0.78-1.17 V in dichloromethane (vs. SCE). Twelve in situ generated primary radical cations were sufficiently stable al lowered temperature in dichloromethane for EPR measurement and showed well resolved HFS. The g-values (approximate to 2.0026) and the coupling constants of 2,5-methyls (a(H) approximate to 1.5 mT), 3,4-methyls (a(H) approximate to 0.35 mT), and of the pyrrole nitrogen (a(N) approximate to 0.42 mT) are very proximate for all 12 radical cations. It can be concluded, with support from quantum chemical calculations, that the odd electron is localised entirely on the pyrrole ring in the a(2) HOMO of the parent molecule. Despite the odd electron distribution, the stability of the radical cations depends on the particular substituent attached to the pyrrole nitrogen.