1-isopropyl-5-methyl-3-pentylpyrrole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-isopropyl-5-methyl-3-pentylpyrrole
• 英文别名: 2-Methyl-4-pentyl-1-propan-2-ylpyrrole
• 化学式: C₁₃H₂₃N
• 分子量: 193.332
• InChiKey: ANNAFYBMPDQDIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  2-bromoheptanal 、 alkaline earth salt of/the/ methylsulfuric acid 在 四丁基溴化铵 、 四氯化钛 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 24.0h， 生成 1-isopropyl-5-methyl-3-pentylpyrrole
  参考文献：
  名称：

  NMR Studies of Five-Coordinate Tin Enolate: An Efficient Reagent for Halo Selective Reaction toward .alpha.-Halo Ketone or .alpha.-Halo Imine

  摘要：

  NMR studies of tin enolates 1, in the presence of HMPA, revealed the presence of a five-coordinate O-stannyl enolate 1(h) which contributes to upfield shifts of Sn peaks in the Sn-119 NMR spectrum and increased coupling constants J(Sn-119-C-13), compared with the four-coordinate tin enolate 1(e). The tautomeric equilibrium between C-stannyl ketone 1(k) and O-stannyl enolate 1(e) was changed by the addition of HMPA, the percentage of enol form being increased. The resulting five-coordinate tin enolates 1(h) showed high reactivity and selectivity for halide displacement in reactions with alpha-halo ketones 2. The tin enolates, when coordinated by Bu(4)NBr, effected a selective reaction with alpha-halo imines 5 to give a variety of gamma-imino ketones 6, which were subsequently hydrolyzed to 1,4-diketones or cyclodehydrated to substituted pyrroles 9.

  DOI：

  10.1021/jo00095a011

文献信息

• NMR Studies of Five-Coordinate Tin Enolate: An Efficient Reagent for Halo Selective Reaction toward .alpha.-Halo Ketone or .alpha.-Halo Imine
  作者：Makoto Yasuda、Yasuhiro Katoh、Ikuya Shibata、Akio Baba、Haruo Matsuda、Noboru Sonoda

  DOI：10.1021/jo00095a011

  日期：1994.8

  NMR studies of tin enolates 1, in the presence of HMPA, revealed the presence of a five-coordinate O-stannyl enolate 1(h) which contributes to upfield shifts of Sn peaks in the Sn-119 NMR spectrum and increased coupling constants J(Sn-119-C-13), compared with the four-coordinate tin enolate 1(e). The tautomeric equilibrium between C-stannyl ketone 1(k) and O-stannyl enolate 1(e) was changed by the addition of HMPA, the percentage of enol form being increased. The resulting five-coordinate tin enolates 1(h) showed high reactivity and selectivity for halide displacement in reactions with alpha-halo ketones 2. The tin enolates, when coordinated by Bu(4)NBr, effected a selective reaction with alpha-halo imines 5 to give a variety of gamma-imino ketones 6, which were subsequently hydrolyzed to 1,4-diketones or cyclodehydrated to substituted pyrroles 9.