(Z)-ethyl 2-(bromo(4-methoxyphenyl)methylene)-4-formylbutanoate | 1357567-09-9

• 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(4-methoxyphenyl)methylene)-4-formylbutanoate
• 英文别名: ethyl (2Z)-2-[bromo-(4-methoxyphenyl)methylidene]-5-oxopentanoate
• CAS: 1357567-09-9
• 化学式: C₁₅H₁₇BrO₄
• 分子量: 341.202
• InChiKey: BQENPBBLMCKFSO-YPKPFQOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙基3-(4-甲氧基苯基)-2-丙炔酸酯 、 烯丙醇 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43%的产率得到(Z)-ethyl 2-(bromo(4-methoxyphenyl)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.