2-(trifluoroacetyl)-5-(trimethylsilyl)furan | 140404-38-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trifluoroacetyl)-5-(trimethylsilyl)furan
• 英文别名: 2-(Trifluoroacetyl)-5-trimethylsilylfuran；2,2,2-trifluoro-1-(5-trimethylsilylfuran-2-yl)ethanone
• CAS: 140404-38-2
• 化学式: C₉H₁₁F₃O₂Si
• 分子量: 236.266
• InChiKey: YXFPRKFXKPOIOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.57
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(trifluoroacetyl)-5-(trimethylsilyl)furan 在 吡啶 、 咪唑 、 sodium tetrahydroborate 、 potassium permanganate 、 18-冠醚-6 、 水 、 二异丁基氢化铝 、 magnesium monoperoxyphthalate hexahydrate 作用下， 以 乙醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 12.0h， 生成 methyl 4-O-(tert-butyldimethylsilyl)-6-deoxy-6,6,6-trifluoro-D-manno-hexopyranoside
  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：

  2-三甲基硅基呋喃 、 三氟乙酸乙酯 在 正丁基锂 作用下， 生成 2-(trifluoroacetyl)-5-(trimethylsilyl)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

• Enzymatic resolution in organic media: synthesis of optically active furanols possessing a fluoroalkyl group
  作者：Mitsunori Takeda、Tatsushi Ishizuka、Keizou Itoh、Tomoya Kitazume

  DOI：10.1016/0022-1139(95)03312-2

  日期：1995.11

  Furanols possessing a fluoroalkyl group were resolved into the corresponding optically active forms via enzymatic esterification in organic media.

  通过在有机介质中的酶促酯化反应，将具有氟代烷基的呋喃醇拆分为相应的旋光形式。
• Synthesis and Stereoisomerization of 2-(1-Alkoxyimino-2,2,2-trifluoroethyl)-5-trimethylsilylfurans
  作者：Yu. Melnik、M. Vorona、G. Veinberg、J. Popelis、L. Ignatovich、E. Lukevics

  DOI：10.1007/s10593-005-0211-7

  日期：2005.6
• Chiral trifluoromethylated 2-butenolides for the construction of 6-deoxy-6,6,6-trifluorosugars
  作者：Takashi Yamazaki、Kenji Mizutani、Mitsunori Takeda、Tomoya Kitazume

  DOI：10.1039/c39920000055

  日期：——

  Optically active 2-butenolides with a trifluoromethyl (CF3) group are synthesized via enzymatic optical resolution and are selectively transformed into 6,6,6-trifluororhodinose and amicetose by base-promoted 1,2-migration of a tert-butyldimethylsilyl moiety in a highly efficient manner.

  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。
• 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.