ethyl (2Z,4R,5R,6E)-5-((tert-butyldimethylsilyl)oxy)-7-phenyl-4-(trifluoromethyl)hepta-2,6-dienoate | 1457998-49-0

• 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: ethyl (2Z,4R,5R,6E)-5-((tert-butyldimethylsilyl)oxy)-7-phenyl-4-(trifluoromethyl)hepta-2,6-dienoate
• CAS: 1457998-49-0
• 化学式: C₂₂H₃₁F₃O₃Si
• 分子量: 428.567
• InChiKey: OYLHGIGKHZVDOZ-VTFIOLEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.39
• 重原子数：
  29.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl (2Z,4R,5R,6E)-5-((tert-butyldimethylsilyl)oxy)-7-phenyl-4-(trifluoromethyl)hepta-2,6-dienoate 在 甲基磺酰胺 、 AD-mix-α 作用下， 以 水 、 叔丁醇 为溶剂， 反应 72.0h， 以67%的产率得到ethyl 2-((2R,3R,4S,5R)-4-((tert-butyldimethylsilyl)oxy)-5-((S)-hydroxy(phenyl)methyl)-3-(trifluoromethyl)tetrahydrofuran-2-yl)acetate
  参考文献：
  名称：

  Total synthesis of γ-trifluoromethylated analogs of goniothalamin and their derivatives

  摘要：

  An efficient method for the construction of chiral gamma-trifluoromethylated alpha,beta-unsaturated delta-lactone, a widely existing pharmacophore, has been developed and successfully applied for synthesis of gamma-trifluoromethylated goniothalamins. The key steps included Evans-Aldol reaction of chiral titanium enolate of alpha-CF3 imide, Wittig olefination and lactonization. The transformation of gamma-trifluoromethylated alpha,beta-unsaturated delta-lactone to a series of trifluoromethylated styryllactones was also investigated. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2013.07.017
• 作为产物：
  描述：

  (2S,3R,E)-1-((S)-4-benzyl-2-thioxooxazolidin-3-yl)-3-hydroxy-5-phenyl-2-(trifluoromethyl)pent-4-en-1-one 在 咪唑 、 2,6-二甲基吡啶 、 lithium aluminium tetrahydride 、 正丁基锂 、 碘 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 28.67h， 生成 ethyl (2Z,4R,5R,6E)-5-((tert-butyldimethylsilyl)oxy)-7-phenyl-4-(trifluoromethyl)hepta-2,6-dienoate 、 ethyl (2E,4R,5R,6E)-5-((tert-butyldimethylsilyl)oxy)-7-phenyl-4-(trifluoromethyl)hepta-2,6-dienoate
  参考文献：
  名称：

  Total synthesis of γ-trifluoromethylated analogs of goniothalamin and their derivatives

  摘要：

  An efficient method for the construction of chiral gamma-trifluoromethylated alpha,beta-unsaturated delta-lactone, a widely existing pharmacophore, has been developed and successfully applied for synthesis of gamma-trifluoromethylated goniothalamins. The key steps included Evans-Aldol reaction of chiral titanium enolate of alpha-CF3 imide, Wittig olefination and lactonization. The transformation of gamma-trifluoromethylated alpha,beta-unsaturated delta-lactone to a series of trifluoromethylated styryllactones was also investigated. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2013.07.017