(S)-4-benzyl-3-((2R,3S,E)-3-((tert-butyldimethylsilyl)oxy)-5-phenyl-2-(trifluoromethyl)pent-4-enoyl)oxazolidin-2-one | 1457998-42-3

• 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: (S)-4-benzyl-3-((2R,3S,E)-3-((tert-butyldimethylsilyl)oxy)-5-phenyl-2-(trifluoromethyl)pent-4-enoyl)oxazolidin-2-one
• CAS: 1457998-42-3
• 化学式: C₂₈H₃₄F₃NO₄Si
• 分子量: 533.663
• InChiKey: PGRRAJXTOBYGOL-UGUHUNCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.86
• 重原子数：
  37.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-4-benzyl-3-((2R,3S,E)-3-((tert-butyldimethylsilyl)oxy)-5-phenyl-2-(trifluoromethyl)pent-4-enoyl)oxazolidin-2-one 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 以77%的产率得到(2R,3S,E)-3-((tert-butyldimethylsilyl)oxy)-N-((S)-1-hydroxy-3-phenylpropan-2-yl)-5-phenyl-2-(trifluoromethyl)pent-4-enamide
  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：

  (4S)-benzyl-3-(3,3,3-trifluoropropanoyl)oxazolidin-2-one 在 2,6-二甲基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.5h， 生成 (S)-4-benzyl-3-((2R,3S,E)-3-((tert-butyldimethylsilyl)oxy)-5-phenyl-2-(trifluoromethyl)pent-4-enoyl)oxazolidin-2-one
  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