(2S,3R)-2-[(2S,3S)-3-phenyloxiran-2-yl]-3-(trifluoromethyl)-2,3-dihydropyran-6-one | 1457998-52-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (2S,3R)-2-[(2S,3S)-3-phenyloxiran-2-yl]-3-(trifluoromethyl)-2,3-dihydropyran-6-one
• CAS: 1457998-52-5
• 化学式: C₁₄H₁₁F₃O₃
• 分子量: 284.235
• InChiKey: VOQYEFMPRIYAGY-LPTSXCQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  在 碳酸氢钠 、 间氯过氧苯甲酸 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 (2S,3R)-2-[(2S,3S)-3-phenyloxiran-2-yl]-3-(trifluoromethyl)-2,3-dihydropyran-6-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

• 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.