(1Z,3E)-2-fluoro-1,4-diphenyl-1,3-butadiene

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: (1Z,3E)-2-fluoro-1,4-diphenyl-1,3-butadiene
• 英文别名: [(1Z,3E)-2-fluoro-4-phenylbuta-1,3-dienyl]benzene
• 化学式: C₁₆H₁₃F
• 分子量: 224.278
• InChiKey: ACGWOUHWQBQXQM-SSLWBDRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• 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：

  β-溴苯乙烯 、 (E)-1-fluoro-2-phenyl-1-[tris(trimethylsilyl)germyl]ethene 在 四(三苯基膦)钯 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以92%的产率得到(1Z,3E)-2-fluoro-1,4-diphenyl-1,3-butadiene
  参考文献：
  名称：

  Pd-catalyzed couplings of (α-fluoro)vinyl tris(trimethylsilyl)germanes

  摘要：

  The (alpha-fluoro)vinyl tris(trimethylsilyl)germanes undergo Pd-catalyzed cross-couplings with aryl and alkenyl halides upon oxidative treatment with hydrogen peroxide under basic aqueous conditions to give access to fluoroalkenes and fluorodienes with retention of stereochemistry. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.023

文献信息

• 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.