(E)-6-bromo-N-methoxy-N-methylhex-2-enamide | 383882-29-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (E)-6-bromo-N-methoxy-N-methylhex-2-enamide
• CAS: 383882-29-9
• 化学式: C₈H₁₄BrNO₂
• 分子量: 236.109
• InChiKey: FFADRCJUPMXOOG-GQCTYLIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-碘代甲苯 、 (E)-6-bromo-N-methoxy-N-methylhex-2-enamide 在 palladium diacetate 降冰片烯 、 三(2-呋喃基)膦 、 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 19.0h， 以84%的产率得到(E)-N-methoxy-N-methyl-2-(8-methyl-3,4-dihydronaphthalen-1(2H)-ylidene)ethanamide
  参考文献：
  名称：

  Palladium-Catalyzed Sequential Alkylation−Alkenylation Reactions and Their Application to the Synthesis of Fused Aromatic Rings

  摘要：

  The synthesis of fused aromatic carbocycles from aryl iodides and difunctional acceptors is outlined. This methodology is based on a palladium-catalyzed aromatic substitution followed by an intramolecular Heck sequence. Under the optimized conditions (Pd(OAc)(2) (10 mol %), tri-2-furylphosphine (20-30 mol %), norbornene (2 equiv), Cs2CO3 (2 equiv), CH3CN, reflux), bromo-enoates react with aryl iodides bearing numerous substituents (F, Cl, CF3, Me, etc.). The expanded description of our initial work as well as the use of polysubstituted aryl iodides is described.

  DOI：

  10.1021/jo0107296
• 作为产物：
  描述：

  (2E)-bromohexenoic acid 在 吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 (E)-6-bromo-N-methoxy-N-methylhex-2-enamide
  参考文献：
  名称：

  Palladium-Catalyzed Sequential Alkylation−Alkenylation Reactions and Their Application to the Synthesis of Fused Aromatic Rings

  摘要：

  The synthesis of fused aromatic carbocycles from aryl iodides and difunctional acceptors is outlined. This methodology is based on a palladium-catalyzed aromatic substitution followed by an intramolecular Heck sequence. Under the optimized conditions (Pd(OAc)(2) (10 mol %), tri-2-furylphosphine (20-30 mol %), norbornene (2 equiv), Cs2CO3 (2 equiv), CH3CN, reflux), bromo-enoates react with aryl iodides bearing numerous substituents (F, Cl, CF3, Me, etc.). The expanded description of our initial work as well as the use of polysubstituted aryl iodides is described.

  DOI：

  10.1021/jo0107296

文献信息

• Palladium-Catalyzed Sequential Alkylation−Alkenylation Reactions and Their Application to the Synthesis of Fused Aromatic Rings
  作者：Mark Lautens、Jean-François Paquin、Sandrine Piguel、Marc Dahlmann

  DOI：10.1021/jo0107296

  日期：2001.11.1

  The synthesis of fused aromatic carbocycles from aryl iodides and difunctional acceptors is outlined. This methodology is based on a palladium-catalyzed aromatic substitution followed by an intramolecular Heck sequence. Under the optimized conditions (Pd(OAc)(2) (10 mol %), tri-2-furylphosphine (20-30 mol %), norbornene (2 equiv), Cs2CO3 (2 equiv), CH3CN, reflux), bromo-enoates react with aryl iodides bearing numerous substituents (F, Cl, CF3, Me, etc.). The expanded description of our initial work as well as the use of polysubstituted aryl iodides is described.