(1'S,4S)-4-<1'-(2',2',2'-trifluoro-1'-hydroxyethyl)>-2-buten-4-olide | 149902-78-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (1'S,4S)-4-<1'-(2',2',2'-trifluoro-1'-hydroxyethyl)>-2-buten-4-olide
• 英文别名: (2S)-2-[(1S)-2,2,2-trifluoro-1-hydroxyethyl]-2H-furan-5-one
• CAS: 149902-78-3
• 化学式: C₆H₅F₃O₃
• 分子量: 182.099
• InChiKey: VDSBGLWCELWYQI-UCORVYFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1'S,4S)-4-<1'-(2',2',2'-trifluoro-1'-hydroxyethyl)>-2-buten-4-olide 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 (1'S,5S)-5-<1'-(2',2',2'-trifluoro-1'-hydroxyethyl)>dihydro-2(3H)-furanone 、 (1'S,4S)-4-<1'-<1'-(tert-butyldimethylsiloxy)-2',2',2'-trifluoroethyl>>-2-(tert-butyldimethylsilyl)-2-buten-4-olide
  参考文献：
  名称：

  Development of a novel pathway to access 6-deoxy-6,6,6-trifluoro sugars via 1,2-migration of a tert-butyldimethylsilyl group

  摘要：

  Trifluoromethylated furanols 2 were enzymatically resolved into the corresponding optically active forms in a highly efficient manner and were further converted to the synthetically useful 2-butenolides 6. Introduction of substituents into these butenolides 6 or their saturated lactone forms 8 was realized by boron trifluoride-mediated Michael addition of cuprates or by capture of the enolates with various kinds of electrophiles, respectively, both of which proceeded with a high degree of diastereoselectivity. Moreover, novel synthetic routes to access 6-deoxy-6,6,6-trifluorosugars were developed by the utilization of 1,2-silyl migration as a key step, which was qualitatively supported by PM3 molecular orbital calculation.

  DOI：

  10.1021/jo00068a033
• 作为产物：
  描述：

  2-<1'-(2',2',2'-trifluoro-1'-hydroxyethyl)>-5-(trimethylsilyl)furan 在 吡啶 、 咪唑 、 水 、 magnesium monoperoxyphthalate hexahydrate 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 12.0h， 生成 (1'S,4S)-4-<1'-(2',2',2'-trifluoro-1'-hydroxyethyl)>-2-buten-4-olide
  参考文献：
  名称：

  Development of a novel pathway to access 6-deoxy-6,6,6-trifluoro sugars via 1,2-migration of a tert-butyldimethylsilyl group

  摘要：

  Trifluoromethylated furanols 2 were enzymatically resolved into the corresponding optically active forms in a highly efficient manner and were further converted to the synthetically useful 2-butenolides 6. Introduction of substituents into these butenolides 6 or their saturated lactone forms 8 was realized by boron trifluoride-mediated Michael addition of cuprates or by capture of the enolates with various kinds of electrophiles, respectively, both of which proceeded with a high degree of diastereoselectivity. Moreover, novel synthetic routes to access 6-deoxy-6,6,6-trifluorosugars were developed by the utilization of 1,2-silyl migration as a key step, which was qualitatively supported by PM3 molecular orbital calculation.

  DOI：

  10.1021/jo00068a033