(Z)-ethyl 2-(bromo(phenyl)methylene)-4-formylbutanoate | 1357566-95-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (Z)-ethyl 2-(bromo(phenyl)methylene)-4-formylbutanoate
• 英文别名: ethyl (2Z)-2-[bromo(phenyl)methylidene]-5-oxopentanoate
• CAS: 1357566-95-0
• 化学式: C₁₄H₁₅BrO₃
• 分子量: 311.175
• InChiKey: DNGZQXJKJADGCI-SEYXRHQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  烯丙醇 、 苯丙炔酸乙酯 在 氧气 、 copper(ll) bromide 、 palladium dichloride 作用下， 以 水 、 甲苯 为溶剂， 60.0 ℃ 、101.33 kPa 条件下， 反应 28.0h， 以70%的产率得到(Z)-ethyl 2-(bromo(phenyl)methylene)-4-formylbutanoate
  参考文献：
  名称：

  Synthesis of δ-Bromo γ,δ-Unsaturated Carbonyl Compounds via Palladium-Catalyzed Bromoalkylation of Alkynoates

  摘要：

  Palladium-catalyzed regio- and stereoselective intermolecular tandem reaction of electron-deficient alkynes, CuBr2, and allylic alcohol to synthesize delta-bromo-gamma,delta-unsaturated carbonyls was developed. A mechanism involving bromopalladation of alkyne, followed by insertion of allylic alcohol and allylic hydrogen shift, is proposed. The shift of allylic hydrogen is the rate-limiting step in this reaction.

  DOI：

  10.1021/jo202416h

文献信息

• Synthesis of δ-Bromo γ,δ-Unsaturated Carbonyl Compounds via Palladium-Catalyzed Bromoalkylation of Alkynoates
  作者：Yanmei Wen、Liangbin Huang、Huanfeng Jiang、Huoji Chen

  DOI：10.1021/jo202416h

  日期：2012.2.17

  Palladium-catalyzed regio- and stereoselective intermolecular tandem reaction of electron-deficient alkynes, CuBr2, and allylic alcohol to synthesize delta-bromo-gamma,delta-unsaturated carbonyls was developed. A mechanism involving bromopalladation of alkyne, followed by insertion of allylic alcohol and allylic hydrogen shift, is proposed. The shift of allylic hydrogen is the rate-limiting step in this reaction.