(E)-(1-fluoroprop-1-ene-1,3-diyl)dibenzene | 85371-02-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-(1-fluoroprop-1-ene-1,3-diyl)dibenzene
• 英文别名: (E)-1-Fluoro-1,3-diphenylpropene；[(E)-1-fluoro-3-phenylprop-1-enyl]benzene
• CAS: 85371-02-4
• 化学式: C₁₅H₁₃F
• 分子量: 212.267
• InChiKey: WBVHNCITNAMZHO-NTCAYCPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  (E)-N'-(1,3-diphenylpropylidene)-2,4,6-triisopropylbenzenesulfonohydrazide 在 正丁基锂 、 氟双(苯基磺酰基)甲烷 作用下， 以 四氢呋喃 为溶剂， 反应 3.33h， 生成 (E)-(1-fluoroprop-1-ene-1,3-diyl)dibenzene 、 (Z)-(1-fluoroprop-1-ene-1,3-diyl)dibenzene
  参考文献：
  名称：

  Preparation of Fluoroalkenes via the Shapiro Reaction: Direct Access to Fluorinated Peptidomimetics

  摘要：

  Fluoroalkenes represent a useful class of peptidomimetics with distinct biophysical properties. Current preparations of this functional group commonly provide mixtures of E- or Z-fluoroalkene diastereomers, and/or mixtures of nonfluorinated products. To directly access fluoroalkenes in good stereoselectivity, a Shapiro fluorination reaction was developed. Fluoroalkene products were accessed in one- or two-step sequences from widely available ketones. This strategy should be useful for the preparation of fluorinated analogs of peptide-based therapeutics, many of which would be challenging to prepare by alternate strategies.

  DOI：

  10.1021/ol401637n

文献信息

• Copper(I)-catalyzed coupling reaction between phenylmagnesium bromide and 3,3,3-trifluoropropene
  作者：Donald E. Bergstrom、Mae W. Ng、James J. Wong

  DOI：10.1021/jo00159a024

  日期：1983.6
• Preparation of Fluoroalkenes via the Shapiro Reaction: Direct Access to Fluorinated Peptidomimetics
  作者：Ming-Hsiu Yang、Siddharth S. Matikonda、Ryan A. Altman

  DOI：10.1021/ol401637n

  日期：2013.8.2

  Fluoroalkenes represent a useful class of peptidomimetics with distinct biophysical properties. Current preparations of this functional group commonly provide mixtures of E- or Z-fluoroalkene diastereomers, and/or mixtures of nonfluorinated products. To directly access fluoroalkenes in good stereoselectivity, a Shapiro fluorination reaction was developed. Fluoroalkene products were accessed in one- or two-step sequences from widely available ketones. This strategy should be useful for the preparation of fluorinated analogs of peptide-based therapeutics, many of which would be challenging to prepare by alternate strategies.