N-allyl-N-methylpyrrole-2-carboxamide | 846542-28-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-allyl-N-methylpyrrole-2-carboxamide
• 英文别名: N-methyl-N-prop-2-enyl-1H-pyrrole-2-carboxamide
• CAS: 846542-28-7
• 化学式: C₉H₁₂N₂O
• 分子量: 164.207
• InChiKey: NJNSMDKHCASGEZ-UHFFFAOYSA-N

物化性质

• 沸点：
  330.0±25.0 °C(Predicted)
• 密度：
  1.086±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  N-allyl-N-methylpyrrole-2-carboxamide 在 palladium diacetate 四丁基氯化铵 、 sodium acetate 作用下， 以 二甲基亚砜 为溶剂， 反应 72.0h， 以62%的产率得到2,4-dimethylpyrrolo[1,2-a]pyrazin-1(2H)-one
  参考文献：
  名称：

  Pd-catalyzed intramolecular cyclization of pyrrolo-2-carboxamides: regiodivergent routes to pyrrolo-pyrazines and pyrrolo-pyridines

  摘要：

  Treatment of N-alkyl-N-allyl-pyrrolo-2-carboxamides with catalytic amounts of palladium derivatives gave regioselectively intramolecular cyclizations to generate bicyclic pyrrolo-fused structures. Pyrrolo[1,2-a]pyrazin-1-ones were achieved in high yields by an amination reaction, while pyrrolo [2,3-c]pyridin-7-ones and pyrrolo[3,2-c]pyridin-4-ones were obtained by an oxidative coupling process. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.11.066
• 作为产物：
  描述：

  N-甲基烯丙基胺 、 吡咯-2-羧酸 在 氯化亚砜 、 TEA 作用下， 以 甲苯 、 二氯甲烷 为溶剂， 反应 6.0h， 以93%的产率得到N-allyl-N-methylpyrrole-2-carboxamide
  参考文献：
  名称：

  Pd-catalyzed intramolecular cyclization of pyrrolo-2-carboxamides: regiodivergent routes to pyrrolo-pyrazines and pyrrolo-pyridines

  摘要：

  Treatment of N-alkyl-N-allyl-pyrrolo-2-carboxamides with catalytic amounts of palladium derivatives gave regioselectively intramolecular cyclizations to generate bicyclic pyrrolo-fused structures. Pyrrolo[1,2-a]pyrazin-1-ones were achieved in high yields by an amination reaction, while pyrrolo [2,3-c]pyridin-7-ones and pyrrolo[3,2-c]pyridin-4-ones were obtained by an oxidative coupling process. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.11.066

文献信息

• Pd-catalyzed intramolecular cyclization of pyrrolo-2-carboxamides: regiodivergent routes to pyrrolo-pyrazines and pyrrolo-pyridines
  作者：Egle M. Beccalli、Gianluigi Broggini、Michela Martinelli、Giuseppe Paladino

  DOI：10.1016/j.tet.2004.11.066

  日期：2005.1

  Treatment of N-alkyl-N-allyl-pyrrolo-2-carboxamides with catalytic amounts of palladium derivatives gave regioselectively intramolecular cyclizations to generate bicyclic pyrrolo-fused structures. Pyrrolo[1,2-a]pyrazin-1-ones were achieved in high yields by an amination reaction, while pyrrolo [2,3-c]pyridin-7-ones and pyrrolo[3,2-c]pyridin-4-ones were obtained by an oxidative coupling process. (C) 2004 Elsevier Ltd. All rights reserved.