1-((E)-2-Bromo-2-fluoro-vinyl)-3,5-dimethoxy-benzene | 402490-59-9

• 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: 1-((E)-2-Bromo-2-fluoro-vinyl)-3,5-dimethoxy-benzene
• 英文别名: 1-(2-bromo-2-fluoroethenyl)-3,5-dimethoxybenzene
• CAS: 402490-59-9
• 化学式: C₁₀H₁₀BrFO₂
• 分子量: 261.091
• InChiKey: QRONKLZTSAZBGX-UHFFFAOYSA-N

物化性质

• 沸点：
  314.2±42.0 °C(Predicted)
• 密度：
  1.447±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-((E)-2-Bromo-2-fluoro-vinyl)-3,5-dimethoxy-benzene 在 bis-triphenylphosphine-palladium(II) chloride 盐酸 、 四丁基氟化铵 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 41.0h， 生成 fluoropterostilbene
  参考文献：
  名称：

  Fluorinated resveratrol and pterostilbene

  摘要：

  A general method for the synthesis of polyhydroxylated stilbene monofluorinated on the central double bond based on the Suzuki reaction between a bromofluoroolefin and a phenylboronic acid is described. Synthesis Of fluorinated analogues of resveratrol and pterostilbene was achieved using this strategy. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01800-7
• 作为产物：
  描述：

  氟三溴甲烷 、 3,5-二甲氧基苯甲醛 在 锌铜偶 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以55%的产率得到1-((E)-2-Bromo-2-fluoro-vinyl)-3,5-dimethoxy-benzene
  参考文献：
  名称：

  Fluorinated resveratrol and pterostilbene

  摘要：

  A general method for the synthesis of polyhydroxylated stilbene monofluorinated on the central double bond based on the Suzuki reaction between a bromofluoroolefin and a phenylboronic acid is described. Synthesis Of fluorinated analogues of resveratrol and pterostilbene was achieved using this strategy. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01800-7

文献信息

• FGFR4 INHIBITOR AND PREPARATION METHOD AND USE THEREOF
  申请人：Guangdong Zhongsheng Pharmaceutical Co., Ltd

  公开号：EP3543227B1

  公开（公告）日：2020-12-30
• Palladium-Catalyzed Stereoconvergent Formylation of (<i>E</i>/<i>Z</i>)-β-Bromo-β-fluorostyrenes: Straightforward Access to (<i>Z</i>)-α-Fluorocinnamic Aldehydes and (<i>Z</i>)-β-Fluorocinnamic Alcohols
  作者：Rajae Zemmouri、Mohammed Kajjout、Yves Castanet、Said Eddarir、Christian Rolando

  DOI：10.1021/jo200798h

  日期：2011.10.7

  We report here the stereoconvergent formylation of (E/Z)-beta-bromo-beta-fluorostyrene mixtures with carbon monoxide and sodium formate catalyzed by palladium. Optimization of reaction conditions leads to the corresponding pure (Z)-alpha-fluorocinnamaldehydes in good yields. The reaction was extended to styrenes bearing electro-attracting or electro-donating groups. The obtained alpha-fluoroaldehydes were smoothly reduced to the corresponding (Z)-beta-fluorocinnamic alcohol by NaBH4. The reaction could be performed on functionalized substrates as demonstrated by the access to the glucoside of beta-fluoroconiferyl alcohol, (Z)-beta-fluoroconiferin, a strong inhibitor of lignin polymerization.