N-(2-allylphenyl)-N-tosylacetamide | 1180844-34-1

• 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-(2-allylphenyl)-N-tosylacetamide
• 英文别名: N-acyl-N-tosyl-2-allylaniline；N-(4-methylphenyl)sulfonyl-N-(2-prop-2-enylphenyl)acetamide
• CAS: 1180844-34-1
• 化学式: C₁₈H₁₉NO₃S
• 分子量: 329.42
• InChiKey: DLWVWINRSNRETG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-allylphenyl)-N-tosylacetamide 在 Hoveyda-Grubbs catalyst second generation 、 氨 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 36.0h， 生成 (E)-N-(2-(4-hydroxyhexa-2,5-dien-1-yl)phenyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Iron-Catalyzed Synthesis of α-Dienyl Five- and Six-Membered N-Heterocycles

  摘要：

  The iron‐catalyzed synthesis of α‐dienyl N‐heterocycles is reported. The method is cost‐effective, atom‐economic, and led to a range of substituted α‐dienyl heterocycles in moderate to good yields and diastereoselectivities. The α‐dienyl piperidines are key synthetic intermediates as demonstrated by the preparation of a panel of α‐polyenyl N‐heterocycles.

  DOI：

  10.1002/ejoc.201700977
• 作为产物：
  描述：

  2-allyl-phenylamine 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 N-(2-allylphenyl)-N-tosylacetamide
  参考文献：
  名称：

  Iron-Catalyzed Synthesis of α-Dienyl Five- and Six-Membered N-Heterocycles

  摘要：

  The iron‐catalyzed synthesis of α‐dienyl N‐heterocycles is reported. The method is cost‐effective, atom‐economic, and led to a range of substituted α‐dienyl heterocycles in moderate to good yields and diastereoselectivities. The α‐dienyl piperidines are key synthetic intermediates as demonstrated by the preparation of a panel of α‐polyenyl N‐heterocycles.

  DOI：

  10.1002/ejoc.201700977

文献信息

• Copper-Catalyzed Enantioselective Intramolecular Alkene Amination/Intermolecular Heck-Type Coupling Cascade
  作者：Timothy W. Liwosz、Sherry R. Chemler

  DOI：10.1021/ja211272v

  日期：2012.2.1

  Enantioselective copper-catalyzed cyclization of γ-alkenylsulfonamides and a δ-alkenylsulfonamide in the presence of a range of vinyl arenes results in variously functionalized 2-substituted chiral nitrogen heterocycles via a formal alkene C-H functionalization process. Application of this reaction to the concise synthesis of a 5-HT(7) receptor antagonist is demonstrated.

  在一系列乙烯基芳烃存在下，γ-烯基磺酰胺和 δ-烯基磺酰胺的对映选择性铜催化环化通过正式的烯烃 CH 官能化过程产生各种官能化的 2-取代手性氮杂环。证明了该反应在 5-HT(7) 受体拮抗剂的简明合成中的应用。
• Olefinic-Amide and Olefinic-Lactam Cyclizations
  作者：Jie Zhou、Jon D. Rainier

  DOI：10.1021/ol901448n

  日期：2009.8.20

  Olefinic-amide and olefinic-lactam cyclization reactions that result in the generation of cyclic enamides are described.
• Iron-Catalyzed Synthesis of α-Dienyl Five- and Six-Membered N-Heterocycles
  作者：Laurine Gonnard、Amandine Guérinot、Janine Cossy

  DOI：10.1002/ejoc.201700977

  日期：2017.11.9

  The iron‐catalyzed synthesis of α‐dienyl N‐heterocycles is reported. The method is cost‐effective, atom‐economic, and led to a range of substituted α‐dienyl heterocycles in moderate to good yields and diastereoselectivities. The α‐dienyl piperidines are key synthetic intermediates as demonstrated by the preparation of a panel of α‐polyenyl N‐heterocycles.