1-(2,2-diethyl-butyryl)-1H-pyrrole-3-carboxylic acid N-allyl-N-tert-butylamide | 671184-02-4

• 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-(2,2-diethyl-butyryl)-1H-pyrrole-3-carboxylic acid N-allyl-N-tert-butylamide
• 英文别名: N-tert-butyl-1-(2,2-diethylbutanoyl)-N-prop-2-enylpyrrole-3-carboxamide
• CAS: 671184-02-4
• 化学式: C₂₀H₃₂N₂O₂
• 分子量: 332.486
• InChiKey: POWTTXJIRASRRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  42.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2,2-diethyl-butyryl)-1H-pyrrole-3-carboxylic acid N-allyl-N-tert-butylamide 在 palladium on activated charcoal 盐酸 、 氢气 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 65.5h， 生成 1-(2,2-diethyl-butyryl)-3-methyl-2-(3-oxopropyl)-pyrrolidine-3-carboxy;ic acid tert-butylamide
  参考文献：
  名称：

  Nucleophilic Addition to Electron-Rich Heteroaromatics:  Dearomatizing Anionic Cyclizations of Pyrrolecarboxamides

  摘要：

  Despite its electron-rich nature, a pyrrole ring is susceptible to intramolecular nucleophilic attack by organolithiums. The resulting dearomatizing anionic cyclization yields new 5- or 7-membered heterocyclic rings. Formation of a new 5-membered ring, by cyclization of an N-benzylpyrrolecarboxamide, is accompanied by ring opening of the original pyrrole to yield 3-aminovinylpyrrolinones. Formation of a new 7-membered ring, by cyclization of an N-allyl pyrrolecarboxamide, yields bicyclic pyrroloazepinones.

  DOI：

  10.1021/ol0364071
• 作为产物：
  描述：

  N-叔丁基丙烯酰胺 在 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.5h， 生成 1-(2,2-diethyl-butyryl)-1H-pyrrole-3-carboxylic acid N-allyl-N-tert-butylamide
  参考文献：
  名称：

  Nucleophilic Addition to Electron-Rich Heteroaromatics:  Dearomatizing Anionic Cyclizations of Pyrrolecarboxamides

  摘要：

  Despite its electron-rich nature, a pyrrole ring is susceptible to intramolecular nucleophilic attack by organolithiums. The resulting dearomatizing anionic cyclization yields new 5- or 7-membered heterocyclic rings. Formation of a new 5-membered ring, by cyclization of an N-benzylpyrrolecarboxamide, is accompanied by ring opening of the original pyrrole to yield 3-aminovinylpyrrolinones. Formation of a new 7-membered ring, by cyclization of an N-allyl pyrrolecarboxamide, yields bicyclic pyrroloazepinones.

  DOI：

  10.1021/ol0364071

文献信息

• Nucleophilic Addition to Electron-Rich Heteroaromatics:  Dearomatizing Anionic Cyclizations of Pyrrolecarboxamides
  作者：Jonathan Clayden、Rachel Turnbull、Ivan Pinto

  DOI：10.1021/ol0364071

  日期：2004.2.1

  Despite its electron-rich nature, a pyrrole ring is susceptible to intramolecular nucleophilic attack by organolithiums. The resulting dearomatizing anionic cyclization yields new 5- or 7-membered heterocyclic rings. Formation of a new 5-membered ring, by cyclization of an N-benzylpyrrolecarboxamide, is accompanied by ring opening of the original pyrrole to yield 3-aminovinylpyrrolinones. Formation of a new 7-membered ring, by cyclization of an N-allyl pyrrolecarboxamide, yields bicyclic pyrroloazepinones.