1H-pyrrole-3-carboxylic acid N-benzyl-N-tert-butylamide | 671183-78-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1H-pyrrole-3-carboxylic acid N-benzyl-N-tert-butylamide
• 英文别名: N-benzyl-N-tert-butyl-1H-pyrrole-3-carboxamide
• CAS: 671183-78-1
• 化学式: C₁₆H₂₀N₂O
• 分子量: 256.348
• InChiKey: GAJXBNSFWKGTIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  36.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1H-pyrrole-3-carboxylic acid N-benzyl-N-tert-butylamide 在 potassium tert-butylate 、 仲丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 18.5h， 生成 N-[2-(5-deutero-1-tert-butyl-2-oxo-5-phenyl-2,5-dihydro-1H-pyrrol-3-yl)-vinyl]-2,2-diethylbutyramide
  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-叔丁基苄胺 在 4-二甲氨基吡啶 、 sodium hydride 作用下， 以 乙醚 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 18.0h， 生成 1H-pyrrole-3-carboxylic acid N-benzyl-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.