methyl 2-(3-phenylnaphthalen-1-yl)acetate | 1325230-25-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 2-(3-phenylnaphthalen-1-yl)acetate
• CAS: 1325230-25-8
• 化学式: C₁₉H₁₆O₂
• 分子量: 276.335
• InChiKey: ZYIGLTSXUVDRNC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  溴乙酸甲酯 、 邻溴苯甲醛 、 2-苯基-1-丙烯 在 palladium diacetate 、 N,N-二异丙基乙胺 、 三(邻甲基苯基)磷 、 锌 作用下， 以 N,N-二甲基乙酰胺 、 苯 为溶剂， 反应 12.0h， 生成 1-甲基-3-苯基萘 、 methyl 2-(3-phenylnaphthalen-1-yl)acetate
  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.