(4S)-benzyl-3-(3,3,3-trifluoropropanoyl)oxazolidin-2-one | 883454-11-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S)-benzyl-3-(3,3,3-trifluoropropanoyl)oxazolidin-2-one
• 英文别名: (4S)-4-benzyl-3-(3,3,3-trifluoropropanoyl)-1,3-oxazolidin-2-one
• CAS: 883454-11-3
• 化学式: C₁₃H₁₂F₃NO₃
• 分子量: 287.238
• InChiKey: KFIWIDUWRJLVPB-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4S)-benzyl-3-(3,3,3-trifluoropropanoyl)oxazolidin-2-one 在 三氟甲磺酸三甲基硅酯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (4S)-benzyl-3-(2-bromo-3,3,3-trifluoropropanoyl)oxazolidin-2-one
  参考文献：
  名称：

  Highly Stereoselective TiCl₄-Catalyzed Evans−Aldol and Et₃Al-Mediated Reformatsky Reactions. Efficient Accesses to Optically Active syn- or anti-α-Trifluoromethyl-β-hydroxy Carboxylic Acid Derivatives

  摘要：

  The TiCl4-catalyzed Evans-aldol reaction of optically active 3,3,3-trifluoropropanoic imide gave the non-Evans syn product stereoselectively, whereas the Reformatsky reaction of 2-bromo-3,3,3-trifluoropropanoic imide in the presence of Et3Al led to the Evans anti product. These new approaches enabled us to synthesize all stereoisomers of trifluoromethylated aldol products for the first time.

  DOI：

  10.1021/ol0531435
• 作为产物：
  描述：

  3,3,3-三氟丙酸 、 (S)-4-benzyl-2-oxazolidinone lithium salt 在 三甲基乙酰氯 、 三乙胺 作用下， 生成 (4S)-benzyl-3-(3,3,3-trifluoropropanoyl)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

文献信息

• A New Access to 3-Halo-3,3-difluoropropanoic Acid Derivatives via Fluorine–Halogen Exchange Reaction of Silyl Enolates of 3,3,3-Trifluoropropanoic Acid Derivatives
  作者：Taichi Shimada、Tsutomu Konno、Takashi Ishihara

  DOI：10.1246/cl.2007.636

  日期：2007.5.5

  On the treatment of silyl enolates derived from N-(3,3,3-trifluoropropanoyl)oxazolidinones with 2.0 equiv. of titanium(IV) halide at −20 °C for 2 h, a novel fluorine–halogen exchange reaction occur...

  用 2.0 当量处理衍生自 N-(3,3,3-三氟丙酰基)恶唑烷酮的甲硅烷基烯醇化物。卤化钛 (IV) 在 -20 °C 下持续 2 小时，会发生一种新的氟 - 卤素交换反应......
• Total synthesis of γ-trifluoromethylated analogs of goniothalamin and their derivatives
  作者：Jun-Ling Chen、Zheng-Wei You、Feng-Ling Qing

  DOI：10.1016/j.jfluchem.2013.07.017

  日期：2013.11

  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.
• Highly Stereoselective TiCl₄-Catalyzed Evans−Aldol and Et₃Al-Mediated Reformatsky Reactions. Efficient Accesses to Optically Active <i>s</i><i>yn</i>- or <i>a</i><i>nti</i>-α-Trifluoromethyl-β-hydroxy Carboxylic Acid Derivatives
  作者：Taichi Shimada、Masamitsu Yoshioka、Tsutomu Konno、Takashi Ishihara

  DOI：10.1021/ol0531435

  日期：2006.3.1

  The TiCl4-catalyzed Evans-aldol reaction of optically active 3,3,3-trifluoropropanoic imide gave the non-Evans syn product stereoselectively, whereas the Reformatsky reaction of 2-bromo-3,3,3-trifluoropropanoic imide in the presence of Et3Al led to the Evans anti product. These new approaches enabled us to synthesize all stereoisomers of trifluoromethylated aldol products for the first time.