(E)-2-(1-fluoro-2-phenylvinyl)naphthalene

• 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)-2-(1-fluoro-2-phenylvinyl)naphthalene
• 英文别名: 2-[(E)-1-fluoro-2-phenylethenyl]naphthalene
• 化学式: C₁₈H₁₃F
• 分子量: 248.3
• InChiKey: CPDPLARZRXHUPF-LDADJPATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  19
• 可旋转键数：
  2
• 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

• 作为产物：
  描述：

  2-styrylnaphthalene 在 氟化氢吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N-溴代乙酰胺 作用下， 以 乙醚 、 二甲基亚砜 为溶剂， 反应 18.0h， 生成 (E)-2-(1-fluoro-2-phenylvinyl)naphthalene
  参考文献：
  名称：

  Synthesis of the K-region monofluoro- and difluorobenzo[c]phenanthrenes

  摘要：

  DOI：

  10.1021/jo00274a026

文献信息

• Regiospecifically Fluorinated Polycyclic Aromatic Hydrocarbons via Julia–Kocienski Olefination and Oxidative Photocyclization. Effect of Fluorine Atom Substitution on Molecular Shape
  作者：Shaibal Banerjee、Saikat Sinha、Padmanava Pradhan、Alessio Caruso、Daniel Liebowitz、Damon Parrish、Miriam Rossi、Barbara Zajc

  DOI：10.1021/acs.joc.5b02580

  日期：2016.5.20

  photocyclizations were performed at higher dilutions. To evaluate the effect of fluorine atom on molecular shapes, X-ray data for 5- and 6-fluorobenzo[c]phenanthrene, 6-fluorochrysene, 9- and 10-fluorobenzo[g]chrysene, and unfluorinated chrysene as well as benzo[g]chrysene were obtained and compared. The fluorine atom caused a small deviation from planarity in the chrysene series and decreased nonplanarity

  描述了区域特异性氟化多环芳烃（PAHs）的模块合成。通过Julia-Kocienski烯烃合成法（产率70-99％）合成的1,2-二芳基氟烯烃被转化为异构的5和6-氟苯并[ c ]菲，5和6-氟苯以及9和10-苯并[ g ]氧化（66-83％的产率）通过氧化光环化而得到。光环化为6-氟代丙烯的过程比1-苯乙烯基萘转化为苯的过程更慢。更高的氟代烯烃稀释度导致更快的环化。因此，以更高的稀释度进行光环化。为了评估氟原子对分子形状的影响，对5-和6-氟苯并[ c ]菲，6-氟丙烯，9-和10-氟苯并[ g ]的X射线数据获得并比较了未氟化的苯和苯并[ g ]苯。氟原子引起了苯并[ c ]菲系列中平面度的小的偏离，并降低了苯并[ c ]菲衍生物的非平面性，但其影响在苯并[ g ]苯系列中最为明显。在9-氟苯并[ g ]丙烯中观察到了该分子的显着扁平化，其中海湾区域F-9和H-8之间的原子间距离短，为2
• Selective Monodefluorination and Wittig Functionalization of <i>gem</i>-Difluoromethyl Groups to Generate Monofluoroalkenes
  作者：Dipendu Mandal、Richa Gupta、Rowan D. Young

  DOI：10.1021/jacs.8b06770

  日期：2018.8.29

  Monodefluorination of gem-difluoromethyl groups is achieved using a frustrated Lewis pair (FLP) approach. Triarylphosphines and group 13 Lewis acids were surveyed as FLP components, with the combination of P(o-Tol)(3) and B(C6F5)(3) found to provide the best results, although the reaction is feasible with more economical components (PPh3 and BF3 center dot OEt2). The alpha-fluoroalkylphosphonium products arising from the reaction were of lower activity, in regard to further fluoride abstraction, as compared to difluoride starting materials, leading to highly selective monodefluorination. The activated substrates were subject to Wittig reaction protocols to generate a variety of monofluoroalkenes in moderate to high yields.
• Synthesis of the K-region monofluoro- and difluorobenzo[c]phenanthrenes
  作者：Seid Mirsadeghi、Ganesh K. B. Prasad、Noel Whittaker、Dhiren R. Thakker

  DOI：10.1021/jo00274a026

  日期：1989.6