(2Z)-2-fluoro-3-[4-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranosyloxy-3-methoxyphenyl]-2-propenal | 1333206-33-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2Z)-2-fluoro-3-[4-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranosyloxy-3-methoxyphenyl]-2-propenal
• 英文别名: [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[4-[(Z)-2-fluoro-3-oxoprop-1-enyl]-2-methoxyphenoxy]oxan-2-yl]methyl acetate
• CAS: 1333206-33-9
• 化学式: C₂₄H₂₇FO₁₂
• 分子量: 526.47
• InChiKey: UWSDLTFFBQJWJD-PNBYVSADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  37
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  150
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  (2Z)-2-fluoro-3-[4-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranosyloxy-3-methoxyphenyl]-2-propenal 在 sodium tetrahydroborate 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 2.0h， 以80%的产率得到2,3,4,6-tetra-O-acetyl-O-[4-((2Z)-2-fluoro-3-hydroxyprop-1-enyl)-2-methoxyphenyl]-β-D-glucopyranoside
  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
• 作为产物：
  描述：

  一氧化碳 、 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium formate 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 80.0 ℃ 、4.0 MPa 条件下， 反应 18.0h， 以61%的产率得到(2Z)-2-fluoro-3-[4-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranosyloxy-3-methoxyphenyl]-2-propenal
  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