(S)-N-(3,3,3-trifluoropropionyl)-4-benzyloxazolidine-2-thione

• 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)-N-(3,3,3-trifluoropropionyl)-4-benzyloxazolidine-2-thione
• 英文别名: 1-[(4S)-4-benzyl-2-sulfanylidene-1,3-oxazolidin-3-yl]-3,3,3-trifluoropropan-1-one
• 化学式: C₁₃H₁₂F₃NO₂S
• 分子量: 303.305
• InChiKey: JTABJKAFYSXYSV-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 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：
  61.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-N-(3,3,3-trifluoropropionyl)-4-benzyloxazolidine-2-thione 在 2,6-二甲基吡啶 、 lithium aluminium tetrahydride 、 四氯化钛 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.83h， 生成 S-4-苄基噁唑烷-2-硫酮
  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：

  3,3,3-三氟丙酸 、 S-4-苄基噁唑烷-2-硫酮 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以88%的产率得到(S)-N-(3,3,3-trifluoropropionyl)-4-benzyloxazolidine-2-thione
  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

• Highly Diastereoselective Aldol Reaction with α-CF3-Substituted Enolates
  作者：Xavier Franck、Blandine Seon-Meniel、Bruno Figadère

  DOI：10.1002/anie.200600927

  日期：2006.8.4
• 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.