2-(tert-butyldimethylsilyl)-5-(trifluoroacetyl)furan | 140167-49-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(tert-butyldimethylsilyl)-5-(trifluoroacetyl)furan
• 英文别名: 5-tert-butyldimethylsilyl-2-(trifluoroacetyl)furan；1-[5-[tert-butyl(dimethyl)silyl]furan-2-yl]-2,2,2-trifluoroethanone
• CAS: 140167-49-3
• 化学式: C₁₂H₁₇F₃O₂Si
• 分子量: 278.346
• InChiKey: ZMQVAYWELKZMCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 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-(tert-butyldimethylsilyl)-5-(trifluoroacetyl)furan 在 sodium tetrahydroborate 作用下， 生成 2-(tert-butyldimethylsilyl)-5-<1'-(2',2',2'-trifluoro-1'-hydroxyethyl)>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
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 正丁基锂 作用下， 生成 2-(tert-butyldimethylsilyl)-5-(trifluoroacetyl)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。
• 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.
• Synthesis and crystal structure of 5-tert-butyldimethylsilyl-2-(2,2,2-trifluoro-hydroxyiminoethyl)furan
  作者：L. Ignatovich、V. Romanov、S. Belyakov、E. Lukevics

  DOI：10.1007/s10593-012-1007-1

  日期：2012.6

  The oximation of 5-tert-butylmethylsilyl-2-(trifluoroacetyl)furan with hydroxylamine leads to the exclusive formation of the E-isomer of 5-tert-butyldimethylsilyl-2-(2,2,2-trifluorohydroxyiminoethyl)- furan.