(R)-ethyl 4,4,4-trifluoro-3-(naphthalen-2-ylthio)butanoate | 1318254-56-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-ethyl 4,4,4-trifluoro-3-(naphthalen-2-ylthio)butanoate
• 英文别名: ethyl (3R)-4,4,4-trifluoro-3-naphthalen-2-ylsulfanylbutanoate
• CAS: 1318254-56-6
• 化学式: C₁₆H₁₅F₃O₂S
• 分子量: 328.355
• InChiKey: BMIVJKAZEXERBP-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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-萘硫醇 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96%的产率得到(R)-ethyl 4,4,4-trifluoro-3-(naphthalen-2-ylthio)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.