| 1333206-27-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 1333206-27-1
• 化学式: C₂₂H₂₄BrFO₁₀
• 分子量: 547.329
• InChiKey: UUAYPHNFJUZJIU-FLTKGPCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.81
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  123.66
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  氟三溴甲烷 、 4-formylphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 zinc/copper couple 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 、
  参考文献：
  名称：

  Palladium-Catalyzed Stereoconvergent Formylation of (E/Z)-β-Bromo-β-fluorostyrenes: Straightforward Access to (Z)-α-Fluorocinnamic Aldehydes and (Z)-β-Fluorocinnamic Alcohols

  摘要：

  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.

  DOI：

  10.1021/jo200798h