Methyl 4-nitro-1H-pyrrole-3-carboxylate | 1195901-57-5

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: Methyl 4-nitro-1H-pyrrole-3-carboxylate
• CAS: 1195901-57-5
• 化学式: C6H6N2O4
• mdl: MFCD12022369
• 分子量: 170.12
• InChiKey: HCJRSSAIKRAHHA-UHFFFAOYSA-N

物化性质

• 沸点：
  374.3±22.0 °C(Predicted)
• 密度：
  1.447±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  87.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对甲基苯磺酰甲基异腈 、 methyl 3-nitroacrylate 在 sodium t-butanolate 作用下， 以 二甲基亚砜 为溶剂， 生成 Methyl 4-nitro-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  Controllable Skeletal and Peripheral Editing of Pyrroles with Vinylcarbenes

  摘要：

  The skeletal editing of azaarenes through insertion, deletion, or swapping of single atoms has recently gained considerable momentum in chemical synthesis. Here, we describe a practical skeletal editing strategy using vinylcarbenes in‐situ generated from trifluoromethyl vinyl N‐triftosylhydrazones, leading to the first dearomative skeletal editing of pyrroles through carbon‐atom insertion. Furthermore, depending on the used catalyst and substrate, three types of peripheral editing reactions of pyrroles are also disclosed: α‐ or γ‐selective C–H insertion, and [3+2] cycloaddition. These controllable molecular editing reactions provide a powerful platform for accessing medicinally relevant CF3‐containing N‐heterocyclic frameworks, such as 2,5‐dihydropyridines, piperidines, azabicyclo[3.3.0]octadienes, and allylated pyrroles from readily available pyrroles. Mechanistic insights from experiments and density functional theory (DFT) calculations shed light on the origin of substrate‐ or catalyst‐controlled chemo‐ and regioselectivity as well as the reaction mechanism.

  DOI：

  10.1002/anie.202401359

文献信息

• Controllable Skeletal and Peripheral Editing of Pyrroles with Vinylcarbenes
  作者：Yong Yang、Qingmin Song、Paramasivam Sivaguru、Zhaohong Liu、Dan Shi、Tian Tian、Graham de Ruiter、Xihe Bi

  DOI：10.1002/anie.202401359

  日期：——

  The skeletal editing of azaarenes through insertion, deletion, or swapping of single atoms has recently gained considerable momentum in chemical synthesis. Here, we describe a practical skeletal editing strategy using vinylcarbenes in‐situ generated from trifluoromethyl vinyl N‐triftosylhydrazones, leading to the first dearomative skeletal editing of pyrroles through carbon‐atom insertion. Furthermore, depending on the used catalyst and substrate, three types of peripheral editing reactions of pyrroles are also disclosed: α‐ or γ‐selective C–H insertion, and [3+2] cycloaddition. These controllable molecular editing reactions provide a powerful platform for accessing medicinally relevant CF3‐containing N‐heterocyclic frameworks, such as 2,5‐dihydropyridines, piperidines, azabicyclo[3.3.0]octadienes, and allylated pyrroles from readily available pyrroles. Mechanistic insights from experiments and density functional theory (DFT) calculations shed light on the origin of substrate‐ or catalyst‐controlled chemo‐ and regioselectivity as well as the reaction mechanism.