methyl (R)-2-benzyloxy-3,3,3-trifluoropropionate | 140404-39-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl (R)-2-benzyloxy-3,3,3-trifluoropropionate
• 英文别名: (2R)-methyl 2-(benzyloxy)-3,3,3-trifluoropropionate；methyl (2R)-3,3,3-trifluoro-2-phenylmethoxypropanoate
• CAS: 140404-39-3
• 化学式: C₁₁H₁₁F₃O₃
• 分子量: 248.202
• InChiKey: YASINZQQUKRMSN-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (R)-3-(2-benzyloxyacetyl)-4-isopropyl-2-oxazolidinone 在 chromium(VI) oxide 、 锂硼氢 、 三乙基硼 、 硫酸 、 lithium diisopropyl amide 作用下， 以 乙醚 、 水 为溶剂， 反应 30.17h， 生成 methyl (R)-2-benzyloxy-3,3,3-trifluoropropionate
  参考文献：
  名称：

  三乙基硼烷介导的碘代三氟甲烷手性酰亚胺烯酸酯的非对映选择性三氟甲基化

  摘要：

  三乙基硼介导的手性N-酰基恶唑烷酮与碘代三氟甲基蒽的锂基端基的锂三氟甲基化反应进行时，非对映异构体过量。

  DOI：

  10.1016/0957-4166(94)80046-4

文献信息

• 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.