2-(tert-butyldimethylsilyl)-5-<(1'-isobutyroyloxy)-2',2',2'-trifluoroethyl>furan | 140404-54-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 2-(tert-butyldimethylsilyl)-5-<(1'-isobutyroyloxy)-2',2',2'-trifluoroethyl>furan
• CAS: 140404-54-2
• 化学式: C₁₆H₂₅F₃O₃Si
• 分子量: 350.453
• InChiKey: CDBNWFUWSLTDBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  39.44
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(tert-butyldimethylsilyl)-5-<(1'-isobutyroyloxy)-2',2',2'-trifluoroethyl>furan 生成 Isobutyric acid (S)-1-[5-(tert-butyl-dimethyl-silanyl)-furan-2-yl]-2,2,2-trifluoro-ethyl ester
  参考文献：
  名称：

  Chiral trifluoromethylated 2-butenolides for the construction of 6-deoxy-6,6,6-trifluorosugars

  摘要：

  带有三氟甲基（CF3）基团的具有光学活性的 2-丁烯酸酯是通过酶促光学解析法合成的，并通过碱促进叔丁基二甲基硅基的 1,2 迁移高效地选择性转化为 6,6,6- 三氟十二烷糖和二十二烷糖。

  DOI：

  10.1039/c39920000055
• 作为产物：
  描述：

  2-(tert-butyldimethylsilyl)-5-(trifluoroacetyl)furan 在 吡啶 、 sodium tetrahydroborate 作用下， 生成 2-(tert-butyldimethylsilyl)-5-<(1'-isobutyroyloxy)-2',2',2'-trifluoroethyl>furan
  参考文献：
  名称：

  Chiral trifluoromethylated 2-butenolides for the construction of 6-deoxy-6,6,6-trifluorosugars

  摘要：

  带有三氟甲基（CF3）基团的具有光学活性的 2-丁烯酸酯是通过酶促光学解析法合成的，并通过碱促进叔丁基二甲基硅基的 1,2 迁移高效地选择性转化为 6,6,6- 三氟十二烷糖和二十二烷糖。

  DOI：

  10.1039/c39920000055

文献信息

• Development of a novel pathway to access 6-deoxy-6,6,6-trifluoro sugars via 1,2-migration of a tert-butyldimethylsilyl group
  作者：Takashi Yamazaki、Kenji Mizutani、Tomoya Kitazume

  DOI：10.1021/jo00068a033

  日期：1993.7

  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.