1-methyl-<2-(2)H>pyrrole | 96213-60-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-methyl-<2-(2)H>pyrrole
• 英文别名: N-Methylpyrrole；2-Deuterio-1-methylpyrrole
• CAS: 96213-60-4
• 化学式: C₅H₇N
• 分子量: 82.1093
• InChiKey: OXHNLMTVIGZXSG-QYKNYGDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-methyl-<2-(2)H>pyrrole 在 lithium tert-butoxide 作用下， 以 二甲基亚砜 为溶剂， 生成 N-methyl-2-pyrrolide
  参考文献：
  名称：

  Zharova, N. G.; Ranneva, Yu. I.; German, E. D., Russian Journal of Physical Chemistry, 1990, vol. 64, # 6, p. 823 - 828

  摘要：

  DOI：
• 作为产物：
  描述：

  N-甲基吡咯 在 正丁基锂 、 重水 作用下， 生成 1-methyl-<2-(2)H>pyrrole
  参考文献：
  名称：

  Brittain, Judith M.; Jones, R. Alan; Arques, Jose Sepulveda, Synthetic Communications, 1982, vol. 12, # 3, p. 231 - 248

  摘要：

  DOI：

文献信息

• Regioselective nucleophilic C-alkylation of the pyrrole ring in an (.eta.-pyrrolyl)iodohydridorhenium complex
  作者：Hugh Felkin、Janusz Zakrzewski

  DOI：10.1021/ja00297a068

  日期：1985.5
• Gas-Phase Reactivity of Ethyl Cations:  Protonation and Alkylation of <i>N</i>-Methylpyrrole and Thiophene
  作者：G. Angelini、R. Bucci、G. Laguzzi、C. Siciliano、A. L. Segre

  DOI：10.1021/jp980899v

  日期：1998.8.1

  The gas-phase reactivity, in terms of deuteration versus alkylation, of radiolytically formed ethyl cations C2D5+ toward N-methylpyrrole and thiophene has been studied in CH4-C2D6 systems at 760 and 1520 Torr and in the presence of variable concentrations of triethylamine (TEA) with the aim of obtaining quantitative data on their competitive behavior. The substrate intramolecular selectivity has also been determined in both reaction channels. The gas-phase behavior of ethyl cations under high-pressure conditions demonstrates their predominant Bronsted versus Lewis acid reactivity toward the selected heteroaromatics, whose branching ratios, at a total pressure of 760 Torr, are 2.34 for N-methylpyrrole and 2.08 for thiophene. Intramolecular selectivity results indicate a substrate alkylation beta:alpha 58:42 for N-methylpyrrole and beta:alpha = 46:54 for thiophene. The substrate deuteration, determined by H-2 NMR, is beta:alpha 50:50 for N-methylpyrrole and beta:alpha = 36:64 for thiophene.