(E)-3-phenyl-1-[(2S,3R,4S)-2,3,4-trimethoxy-3,4-dihydro-2H-pyran-6-yl]prop-2-en-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-3-phenyl-1-[(2S,3R,4S)-2,3,4-trimethoxy-3,4-dihydro-2H-pyran-6-yl]prop-2-en-1-one
• 化学式: C₁₇H₂₀O₅
• 分子量: 304.343
• InChiKey: JNGUIVMOJBDLTC-HMKMJXIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl (methyl 4-O-benzyl-2,3-di-O-methyl-α-D-glucopyranosid)uronate 在 正丁基锂 、 caesium carbonate 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 反应 10.25h， 生成 (E)-3-phenyl-1-[(2S,3R,4S)-2,3,4-trimethoxy-3,4-dihydro-2H-pyran-6-yl]prop-2-en-1-one
  参考文献：
  名称：

  Preparation of Sugar-Derived .beta.-Keto Phosphonates and Their Use in the Synthesis of Higher Sugars

  摘要：

  Sugar-derived beta-keto phosphonates 5, 6, 7, and 8 were synthesised by the acylation of lithium dimethyl methylphosphonate with the corresponding methyl glycuronates 1, 2, and 3 and glyconate 4 in THF at -78 degrees C, respectively. Wadsworth-Emmons reaction of 5, 6, 7, and 8 with various sugar-derived aldehydes proceeded in good yield to produce higher sugar enones. Similarly, C-2 symmetric bis phosphonate 28 derived from L-tartrate 27 was prepared and condensed with various sugar-derived aldehydes to provide C-2 symmetric bis enones in moderate yields. Treatment of the glucose-derived beta-keto phosphonate 5 with various aldehydes and excess Cs2CO3 resulted in complete cis elimination of the C-4 benzyl group along with the Wadsworth-Emmons reaction, leading to cross-conjugated dienones.

  DOI：

  10.1021/jo00100a047

文献信息

• Preparation of Sugar-Derived .beta.-Keto Phosphonates and Their Use in the Synthesis of Higher Sugars
  作者：K. Narkunan、M. Nagarajan

  DOI：10.1021/jo00100a047

  日期：1994.10

  Sugar-derived beta-keto phosphonates 5, 6, 7, and 8 were synthesised by the acylation of lithium dimethyl methylphosphonate with the corresponding methyl glycuronates 1, 2, and 3 and glyconate 4 in THF at -78 degrees C, respectively. Wadsworth-Emmons reaction of 5, 6, 7, and 8 with various sugar-derived aldehydes proceeded in good yield to produce higher sugar enones. Similarly, C-2 symmetric bis phosphonate 28 derived from L-tartrate 27 was prepared and condensed with various sugar-derived aldehydes to provide C-2 symmetric bis enones in moderate yields. Treatment of the glucose-derived beta-keto phosphonate 5 with various aldehydes and excess Cs2CO3 resulted in complete cis elimination of the C-4 benzyl group along with the Wadsworth-Emmons reaction, leading to cross-conjugated dienones.