(E)-tert-butyl 2-(3-butoxy-3-oxoprop-1-en-1-yl)-1H-pyrrole-1-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: (E)-tert-butyl 2-(3-butoxy-3-oxoprop-1-en-1-yl)-1H-pyrrole-1-carboxylate
• 英文别名: tert-butyl 2-[(E)-3-butoxy-3-oxoprop-1-enyl]pyrrole-1-carboxylate
• 化学式: C₁₆H₂₃NO₄
• 分子量: 293.363
• InChiKey: GSKHHTVUABNYQL-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  57.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-tert-butyl 2-(3-butoxy-3-oxoprop-1-en-1-yl)-1H-pyrrole-1-carboxylate 、 丙烯酸苄酯 在 t-butylperoxybenzoate 、 palladium diacetate 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 二甲基亚砜 为溶剂， 反应 48.0h， 以66%的产率得到
  参考文献：
  名称：

  Mild Aerobic Oxidative Palladium (II) Catalyzed C−H Bond Functionalization:  Regioselective and Switchable C−H Alkenylation and Annulation of Pyrroles

  摘要：

  A palladium catalyzed C-H bond functionalization system that operates under ambient and aerobic conditions can be used to alkenylate pyrroles with control of regioselectivty. A steric and electronic control strategy can be used to influence positional control in the C-H bond functionalization process that results in either the C2 or C3 alkenylated products. Air, molecular oxygen, or tBuOOBz can be used as reoxidant in this mild process, and the reaction works on a range of substrates. Finally a catalytic aerobic annulation strategy is described that can be controlled to produce cyclization at either the C2 or C3 positions, thus forming diverse pyrrole products.

  DOI：

  10.1021/ja058141u
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 4-二甲氨基吡啶 、 氧气 、 palladium diacetate 、 4,5-diphenylpyrazolo[1,5-a][1,8]naphthyridine 、 二甲基亚砜 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 30.0~35.0 ℃ 、101.33 kPa 条件下， 反应 26.5h， 生成 (E)-tert-butyl 2-(3-butoxy-3-oxoprop-1-en-1-yl)-1H-pyrrole-1-carboxylate
  参考文献：
  名称：

  吡咯和噻吩的空间控制的 C-H 烯基化

  摘要：

  与电子控制方法相反，Pd 催化的 C-H 烯基化靶向N-烷基吡咯和 3-取代噻吩的受阻位置最小。吡唑并萘啶配体的空间需求和稳定的双齿结合模式是这些使用氧作为氧化剂的空间控制烯基化成功的关键。

  DOI：

  10.1039/d1cc04378a

文献信息

• Sterically controlled C–H alkenylation of pyrroles and thiophenes
  作者：Eunsu Kang、Ju Eun Jeon、Siyeon Jeong、Hyun Tae Kim、Jung Min Joo

  DOI：10.1039/d1cc04378a

  日期：——

  Pd-catalyzed C–H alkenylations targeting the least hindered position of N-alkyl pyrroles and 3-substituted thiophenes, as opposed to electronically controlled approaches, are developed. The steric demand and stable bidentate binding mode of the pyrazolonaphthyridine ligand are key to the success of these sterically controlled alkenylations using oxygen as an oxidant.

  与电子控制方法相反，Pd 催化的 C-H 烯基化靶向N-烷基吡咯和 3-取代噻吩的受阻位置最小。吡唑并萘啶配体的空间需求和稳定的双齿结合模式是这些使用氧作为氧化剂的空间控制烯基化成功的关键。
• Mild Aerobic Oxidative Palladium (II) Catalyzed C−H Bond Functionalization:  Regioselective and Switchable C−H Alkenylation and Annulation of Pyrroles
  作者：Elizabeth M. Beck、Neil P. Grimster、Richard Hatley、Matthew J. Gaunt

  DOI：10.1021/ja058141u

  日期：2006.3.1

  A palladium catalyzed C-H bond functionalization system that operates under ambient and aerobic conditions can be used to alkenylate pyrroles with control of regioselectivty. A steric and electronic control strategy can be used to influence positional control in the C-H bond functionalization process that results in either the C2 or C3 alkenylated products. Air, molecular oxygen, or tBuOOBz can be used as reoxidant in this mild process, and the reaction works on a range of substrates. Finally a catalytic aerobic annulation strategy is described that can be controlled to produce cyclization at either the C2 or C3 positions, thus forming diverse pyrrole products.