ethyl 4-formyl-2-phenyl-1H-pyrrole-3-carboxylate | 1325713-99-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: ethyl 4-formyl-2-phenyl-1H-pyrrole-3-carboxylate
• CAS: 1325713-99-2
• 化学式: C₁₄H₁₃NO₃
• 分子量: 243.262
• InChiKey: QANMPYXVHFYFHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (Z)-ethyl 3-(allylamino)-3-phenylacrylate 在 三乙烯二胺 、 氧气 、 copper diacetate 、 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 3.0h， 以56%的产率得到ethyl 4-formyl-2-phenyl-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  Copper-Mediated Aerobic Synthesis of 3-Azabicyclo[3.1.0]hex-2-enes and 4-Carbonylpyrroles from N-Allyl/Propargyl Enamine Carboxylates

  摘要：

  Synthetic methods for 3-azabicyclo[3.1.0] hex-2-enes and 4-carbonylpyrroles have been developed that use copper-mediated/catalyzed reactions of N-allyl/propargyl enamine carboxylates under an O-2 atmosphere and involve intramolecular cyclopropanation and carbooxygenation, respectively. These methodologies take advantage of orthogonal modes of chemical reactivity of readily available N-allyl/propargyl enamine carboxylates; the complementary pathways can be accessed by slight modification of the reaction conditions.

  DOI：

  10.1021/ja206580j

文献信息

• Electrochemical Organoselenium Catalysis for the Selective Activation of Alkynes: Easy Access to Carbonyl-pyrroles/oxazoles from <i>N</i>-Propargyl Enamines/Amides
  作者：Mrinmay Baidya、Jhilik Dutta、Suman De Sarkar

  DOI：10.1021/acs.orglett.3c01355

  日期：2023.5.26

  Intramolecular electro-oxidative addition of enamines or amides to nonactivated alkynes was attained to access carbonyl-pyrroles or -oxazoles from N-propargyl derivatives. Organoselenium was employed as the electrocatalyst, which played a crucial role as a π-Lewis acid and selectively activated the alkyne for the successful nucleophilic addition. The synthetic strategy permits a wide range of substrate

  实现了烯胺或酰胺对未活化炔烃的分子内电氧化加成，以从N-炔丙基衍生物中获得羰基-吡咯或-恶唑。有机硒被用作电催化剂，它作为π-路易斯酸起着至关重要的作用，并选择性地激活炔烃以成功进行亲核加成。合成策略允许广泛的底物范围，产率高达 93%。几个机械实验，包括硒结合的中间加合物的分离，启发了电催化途径。
• Copper-Mediated Aerobic Synthesis of 3-Azabicyclo[3.1.0]hex-2-enes and 4-Carbonylpyrroles from <i>N</i>-Allyl/Propargyl Enamine Carboxylates
  作者：Kah Kah Toh、Yi-Feng Wang、Eileen Pei Jian Ng、Shunsuke Chiba

  DOI：10.1021/ja206580j

  日期：2011.9.7

  Synthetic methods for 3-azabicyclo[3.1.0] hex-2-enes and 4-carbonylpyrroles have been developed that use copper-mediated/catalyzed reactions of N-allyl/propargyl enamine carboxylates under an O-2 atmosphere and involve intramolecular cyclopropanation and carbooxygenation, respectively. These methodologies take advantage of orthogonal modes of chemical reactivity of readily available N-allyl/propargyl enamine carboxylates; the complementary pathways can be accessed by slight modification of the reaction conditions.