N-(4-nitrophenylsulfonyl)pent-4-enamide | 1310538-66-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(4-nitrophenylsulfonyl)pent-4-enamide
• 英文别名: N-(4-nitrophenyl)sulfonylpent-4-enamide
• CAS: 1310538-66-9
• 化学式: C₁₁H₁₂N₂O₅S
• 分子量: 284.293
• InChiKey: GEIQBEFACWZJCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(4-nitrophenylsulfonyl)pent-4-enamide 在 bis-triphenylphosphine-palladium(II) chloride 、 氧气 、 sodium acetate 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以70%的产率得到
  参考文献：
  名称：

  Opening the Way to Catalytic Aminopalladation/Proxicyclic Dehydropalladation: Access to Methylidene γ-Lactams

  摘要：

  A new aerobic intramolecular palladium(II)-based catalytic system that triggers aminopalladation/dehydropalladation of N-sulfonylalkenylamides to give the corresponding methylidene gamma-lactams has been identified. Use of triphenylphosphine and chloride anion as ligands is mandatory for optimal yields, and molecular oxygen can be used as the sole terminal oxidant. Scope and limitations of the methods are described. A mechanism is proposed on the basis of experimental results as well as density functional theory calculations.

  DOI：

  10.1021/acs.orglett.6b00143
• 作为产物：
  描述：

  4-戊烯酸 、 4-硝基苯磺酰胺 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以95%的产率得到N-(4-nitrophenylsulfonyl)pent-4-enamide
  参考文献：
  名称：

  钯催化的双环杂环的氨基炔化策略：（±）-Trachelanthamidine的合成

  摘要：

  甜蜜的环化反应：吡咯嗪和吲哚并嗪的合成已经完成。烯烃用高价碘试剂TIPS-EBX进行了分子内钯催化的氨基炔基化反应。除去保护基团后，分两步环化，随后还原，得到天然产物（±）-曲安啶（参见方案； TIPS-EBX =三异丙基甲硅烷基乙炔基苯并恶唑啉酮）。

  DOI：

  10.1002/anie.201100718

文献信息

• Cobalt-Catalyzed Aerobic Aminocyclization of Unsaturated Amides for the Synthesis of Functionalized γ- and δ-Lactams
  作者：Manuel Freis、Moritz Balkenhohl、David M. Fischer、Tony Georgiev、Roman C. Sarott、Erick M. Carreira

  DOI：10.1021/acs.orglett.3c02390

  日期：2023.9.1
• A Palladium-Catalyzed Aminoalkynylation Strategy towards Bicyclic Heterocycles: Synthesis of (±)-Trachelanthamidine
  作者：Stefano Nicolai、Cyril Piemontesi、Jérôme Waser

  DOI：10.1002/anie.201100718

  日期：2011.5.9

  Sweet cyclizations: The synthesis of pyrrolizidines and indolizidines has been achieved. Olefins were subjected to an intramolecular palladium‐catalyzed aminoalkynylation with the hypervalent iodine reagent TIPS‐EBX. After removal of the protecting group, a two‐step cyclization sequence and subsequent reduction led to the natural product (±)‐trachelanthamidine (see scheme; TIPS‐EBX=triisopropylsilyl

  甜蜜的环化反应：吡咯嗪和吲哚并嗪的合成已经完成。烯烃用高价碘试剂TIPS-EBX进行了分子内钯催化的氨基炔基化反应。除去保护基团后，分两步环化，随后还原，得到天然产物（±）-曲安啶（参见方案； TIPS-EBX =三异丙基甲硅烷基乙炔基苯并恶唑啉酮）。
• Opening the Way to Catalytic Aminopalladation/Proxicyclic Dehydropalladation: Access to Methylidene γ-Lactams
  作者：Mélanie M. Lorion、Filipe J. S. Duarte、Maria José Calhorda、Julie Oble、Giovanni Poli

  DOI：10.1021/acs.orglett.6b00143

  日期：2016.3.4

  A new aerobic intramolecular palladium(II)-based catalytic system that triggers aminopalladation/dehydropalladation of N-sulfonylalkenylamides to give the corresponding methylidene gamma-lactams has been identified. Use of triphenylphosphine and chloride anion as ligands is mandatory for optimal yields, and molecular oxygen can be used as the sole terminal oxidant. Scope and limitations of the methods are described. A mechanism is proposed on the basis of experimental results as well as density functional theory calculations.