(E)-5-fluoro-2-(2-phenylprop-1-enyl)benzaldehyde | 1325230-40-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-5-fluoro-2-(2-phenylprop-1-enyl)benzaldehyde
• 英文别名: 5-fluoro-2-[(E)-2-phenylprop-1-enyl]benzaldehyde
• CAS: 1325230-40-7
• 化学式: C₁₆H₁₃FO
• 分子量: 240.277
• InChiKey: ATAMFCVCEMMAJR-FMIVXFBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-溴-5-氟苯甲醛 、 2-苯基-1-丙烯 在 palladium diacetate 、 N,N-二异丙基乙胺 、 三(邻甲基苯基)磷 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 2.0h， 生成 (Z)-5-fluoro-2-(2-phenylprop-1-enyl)benzaldehyde 、 (E)-5-fluoro-2-(2-phenylprop-1-enyl)benzaldehyde 、
  参考文献：
  名称：

  Cyclization Reaction for the Synthesis of Polysubstituted Naphthalenes in the Presence of Au(I) Precatalysts

  摘要：

  Au(I)-catalyzed cyclization of alkenyl carbonyl compounds leading to a variety of substituted naphthalenes has been developed. This process exploits a dual function of the Au(I) catalyst: (1) the oxophilic nature of the Au(I) catalyst, counterintuitive to the pi-acidic reactivities generally associated with Au catalysts, and (2) olefin isomerization supported by the outcome of isotope scrambling experiments. It cannot be completely excluded that TfOH is a true operative catalyst in this protocol. In view of the practicality, the unnecessity of isomerically pure starting material in this reaction is particularly attractive and valuable.

  DOI：

  10.1021/jo201339z

文献信息

• Cyclization Reaction for the Synthesis of Polysubstituted Naphthalenes in the Presence of Au(I) Precatalysts
  作者：Arun R. Jagdale、Jong Hyub Park、So Won Youn

  DOI：10.1021/jo201339z

  日期：2011.9.2

  Au(I)-catalyzed cyclization of alkenyl carbonyl compounds leading to a variety of substituted naphthalenes has been developed. This process exploits a dual function of the Au(I) catalyst: (1) the oxophilic nature of the Au(I) catalyst, counterintuitive to the pi-acidic reactivities generally associated with Au catalysts, and (2) olefin isomerization supported by the outcome of isotope scrambling experiments. It cannot be completely excluded that TfOH is a true operative catalyst in this protocol. In view of the practicality, the unnecessity of isomerically pure starting material in this reaction is particularly attractive and valuable.