[3-fluoro-2-methylprop-1-en-1-yl]benzene | 1286796-50-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [3-fluoro-2-methylprop-1-en-1-yl]benzene
• CAS: 1286796-50-6
• 化学式: C₁₀H₁₁F
• 分子量: 150.196
• InChiKey: JZNKXOCCFUOCQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.06
• 重原子数：
  11.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为产物：
  描述：

  (E)-3-phenyl-2-methyl-2-propenol 在 四丁基氟化铵 、 三乙胺 、 三苯基膦 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 叔丁醇 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 [3-fluoro-2-methylprop-1-en-1-yl]benzene 、 [1-fluoro-2-methylprop-2-en-1-yl]benzene
  参考文献：
  名称：

  Palladium-Catalyzed Allylic Fluorination

  摘要：

  DOI：

  10.1002/anie.201007307

文献信息

• Synthesis of α-trifluoromethylated amides by Eschenmoser–Claisen-type rearrangement of allylic alcohols
  作者：Justyna Walkowiak、Magdalena Tomas-Szwaczyk、Günter Haufe、Henryk Koroniak

  DOI：10.1016/j.jfluchem.2012.07.011

  日期：2012.11

  A new, mild method to prepare alpha-trifluoromethylated amides bearing an additional trans-configured double bond in gamma-position is described. Treatment at room temperature of fluorinated and non-fluorinated allylic alcohols 1 and 2 with the 1,1,3,3,3-pentafluoropropene-diethylamine adduct (PFPDEA) in the presence of triethylamine as base gave the products of [3,3]-sigmatropic Eschenmoser-Claisen-type rearrangements with good yields and excellent diastereoselectivity due to chair-like conformations of transition states. Starting with enantiomerically enriched allylic alcohols chirality transfer from carbon 3 of the allylic system to carbon 2 of the final alpha-trifluoromethyl carboxamides was observed. This methodology was applied to both simple and more complex, including terpenic, allylic alcohols and might be developed to an alternative strategy to the well-known electrophilic alpha-trifluoromethylation of carbonyl compounds. (C) 2012 Elsevier B.V. All rights reserved.
• Palladium-Catalyzed Allylic Fluorination
  作者：Charlotte Hollingworth、Amaruka Hazari、Matthew N. Hopkinson、Matthew Tredwell、Elena Benedetto、Mickael Huiban、Antony D. Gee、John M. Brown、Véronique Gouverneur

  DOI：10.1002/anie.201007307

  日期：2011.3.7