(S)-ethyl 4,4,4-trifluoro-3-(phenylthio)butanoate | 1318254-44-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (S)-ethyl 4,4,4-trifluoro-3-(phenylthio)butanoate
• 英文别名: ethyl (3S)-4,4,4-trifluoro-3-phenylsulfanylbutanoate
• CAS: 1318254-44-2
• 化学式: C₁₂H₁₃F₃O₂S
• 分子量: 278.295
• InChiKey: LMOYOMWZBVGFOJ-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4,4,4-三氟巴豆酸乙酯 、 苯硫酚 在 1-[3,5-bis(trifluoromethyl)phenyl]-3-[(S)-[(2S,4S)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methyl]thiourea 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 (S)-ethyl 4,4,4-trifluoro-3-(phenylthio)butanoate 、 (R)-ethyl 4,4,4-trifluoro-3-(phenylthio)butanoate
  参考文献：
  名称：

  Organocatalytic Asymmetric Sulfa-Michael Addition of Thiols to 4,4,4-Trifluorocrotonates

  摘要：

  The first asymmetric sulfa-Michael addition of thiols to 4,4,4-trifluorocrotonates for the construction of a stereogenic center bearing a unique trifluoromethyl group and a sulfur atom has been achieved in high yields and excellent enantioselectivities with a 1 mol % bifunctional organocatalyst. Subsequent transformation led to the expedient preparation of enantioenriched thiochroman-4-one and the key intermediate of the potent inhibitor of MMP-3, (R)-gamma-trifluoromethyl gamma-sulfone hydroxamate.

  DOI：

  10.1021/ol201766k

文献信息

• Organocatalytic Asymmetric Sulfa-Michael Addition of Thiols to 4,4,4-Trifluorocrotonates
  作者：Xiu-Qin Dong、Xin Fang、Chun-Jiang Wang

  DOI：10.1021/ol201766k

  日期：2011.8.19

  The first asymmetric sulfa-Michael addition of thiols to 4,4,4-trifluorocrotonates for the construction of a stereogenic center bearing a unique trifluoromethyl group and a sulfur atom has been achieved in high yields and excellent enantioselectivities with a 1 mol % bifunctional organocatalyst. Subsequent transformation led to the expedient preparation of enantioenriched thiochroman-4-one and the key intermediate of the potent inhibitor of MMP-3, (R)-gamma-trifluoromethyl gamma-sulfone hydroxamate.