ethyl 4,4,4-trifluoro-3-phenylthiobutyrate | 607360-69-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: ethyl 4,4,4-trifluoro-3-phenylthiobutyrate
• 英文别名: ethyl 4,4,4-trifluoro-3-(phenylthio)butanoate；Ethyl 4,4,4-trifluoro-3-(phenylsulfanyl)butanoate；ethyl 4,4,4-trifluoro-3-phenylsulfanylbutanoate
• CAS: 607360-69-0
• 化学式: C₁₂H₁₃F₃O₂S
• 分子量: 278.295
• InChiKey: LMOYOMWZBVGFOJ-UHFFFAOYSA-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 三乙胺 作用下， 生成 ethyl 4,4,4-trifluoro-3-phenylthiobutyrate
  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

• ——
  作者：N. M. Karimova、A. A. Glazkov、A. V. Ignatenko、A. F. Kolomiets

  DOI：10.1023/a:1025661630048

  日期：——

  Ethyl 4,4,4-trifluorocrotonate I readily adds aliphatic and aromatic thiols and aminothiols at the double bond in the presence of catalytic amounts of alkylamines and ammonia to give 3-thiolation products. Thiolacetic acid reacts with ester I in the absence of a catalyst at 100degreesC.
• KITAZUME, TOMOYA;MURATA, KOUICHI;KOKUSHO, YOSHITAKA;IWASAKI, SHINJIRO, J. FLUOR. CHEM.,(1988) N 1, 75-86
  作者：KITAZUME, TOMOYA、MURATA, KOUICHI、KOKUSHO, YOSHITAKA、IWASAKI, SHINJIRO

  DOI：——

  日期：——
• 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.