(R)-ethyl 3-(o-tolylthio)-4,4,4-trifluorobutanoate | 1318254-47-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (R)-ethyl 3-(o-tolylthio)-4,4,4-trifluorobutanoate
• 英文别名: ethyl (3R)-4,4,4-trifluoro-3-(2-methylphenyl)sulfanylbutanoate
• CAS: 1318254-47-5
• 化学式: C₁₃H₁₅F₃O₂S
• 分子量: 292.322
• InChiKey: DNWTWGGWUURSCZ-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  ethyl (Z)-4,4,4-trifluorobut-2-enoate 、 2-巯基甲苯 在 N-((1R,2R)-2-(3-((1R,2R)-2-(dimethylamino)cyclohexyl)thioureido)-1,2-diphenylethyl)-3,5-bis(trifluoromethyl)benzenesulfonamide 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以92%的产率得到(R)-ethyl 3-(o-tolylthio)-4,4,4-trifluorobutanoate
  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.