2-fluoro-6-phenylnaphthalene | 1214368-85-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-fluoro-6-phenylnaphthalene
• 英文别名: 6-Fluoro-2-phenylnaphthalene
• CAS: 1214368-85-0
• 化学式: C₁₆H₁₁F
• 分子量: 222.262
• InChiKey: PHZICPQHLRYOOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-fluoro-6-phenylnaphthalene 、 联硼酸新戊二醇酯 在 bis(1,5-cyclooctadiene)nickel (0) 、 sodium phenoxide 、 三环己基膦 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以67%的产率得到5,5-dimethyl-2-(6-phenylnaphthalen-2-yl)-1,3,2-dioxaborinane
  参考文献：
  名称：

  通过 C-F 裂解镍催化芳基氟化物硼化

  摘要：

  描述了通过 CF 活化的镍催化硼化。该协议的特点是范围广泛，包括未激活的氟芳烃，但不影响其效率和可扩展性，因此代表了朝着 CF 激活协议的实施迈出的重要一步。

  DOI：

  10.1021/jacs.5b08103
• 作为产物：
  描述：

  5-fluoro-2-(2-oxo-2-phenylethyl)benzaldehyde 、 苯乙炔 在 iron(III) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 以80%的产率得到2-fluoro-6-phenylnaphthalene
  参考文献：
  名称：

  Iron-catalyzed Benzannulation Reactions of 2-Alkylbenzaldehydes and Alkynes Leading to Naphthalene Derivatives

  摘要：

  An efficient and practical method for the synthesis of naphthalene derivatives via Fe(III)-catalyzed benzannulation of 2-(2-ozoethyl)-benzaldehydes and alkynes has been developed. The system holds the advantages of cheap catalysts, wide substrate scope, and mild reaction conditions.

  DOI：

  10.1021/ol4000394

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.
• Iron-catalyzed Benzannulation Reactions of 2-Alkylbenzaldehydes and Alkynes Leading to Naphthalene Derivatives
  作者：Shifa Zhu、Yelin Xiao、Zhengjiang Guo、Huanfeng Jiang

  DOI：10.1021/ol4000394

  日期：2013.2.15

  An efficient and practical method for the synthesis of naphthalene derivatives via Fe(III)-catalyzed benzannulation of 2-(2-ozoethyl)-benzaldehydes and alkynes has been developed. The system holds the advantages of cheap catalysts, wide substrate scope, and mild reaction conditions.
• Ni-Catalyzed Borylation of Aryl Fluorides via C–F Cleavage
  作者：Xiang-Wei Liu、Javier Echavarren、Cayetana Zarate、Ruben Martin

  DOI：10.1021/jacs.5b08103

  日期：2015.10.7

  A Ni-catalyzed borylation via C-F activation is described. This protocol is distinguished by a wide scope, including unactivated fluoroarenes, without compromising its efficiency and scalability, thus representing a significant step-forward toward the implementation of C-F activation protocols.

  描述了通过 CF 活化的镍催化硼化。该协议的特点是范围广泛，包括未激活的氟芳烃，但不影响其效率和可扩展性，因此代表了朝着 CF 激活协议的实施迈出的重要一步。