(R)-2,2,2-trifluoro-1-(4-methyltiophenyl)-1-(1H-pyrrol-2-yl)ethanol | 1096375-81-3

• 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)-2,2,2-trifluoro-1-(4-methyltiophenyl)-1-(1H-pyrrol-2-yl)ethanol
• 英文别名: (R)-1-[4-(Methylthio)phenyl]-1-(1H-pyrrole-2-yl)-2,2,2-trifluoroethanol；(1R)-2,2,2-trifluoro-1-(4-methylsulfanylphenyl)-1-(1H-pyrrol-2-yl)ethanol
• CAS: 1096375-81-3
• 化学式: C₁₃H₁₂F₃NOS
• 分子量: 287.306
• InChiKey: UACMIMYLCSKXCO-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  61.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  吡咯 、 2,2,2-三氟-1-[4-(甲硫基)苯基]乙酮 在 zirconium(IV) tert-butoxide 、 (S)-3,3'-二溴-1,1'-联-2-萘酚 作用下， 以 苯 为溶剂， 反应 1.0h， 以84%的产率得到(R)-2,2,2-trifluoro-1-(4-methyltiophenyl)-1-(1H-pyrrol-2-yl)ethanol
  参考文献：
  名称：

  Enantioselective Zirconium-Catalyzed Friedel−Crafts Alkylation of Pyrrole with Trifluoromethyl Ketones

  摘要：

  The first catalytic enantioselective Friedel-Crafts alkylation of pyrrole with 2,2,2-trifluoroacetophenones to give pyrroles with a trifluoromethyl-substituted tertiary alcohol moiety bearing a quaternary stereogenic center is described. The reaction is achieved in the presence of a 3,3'dibromo-BINOL-Zr(IV) complex to give the expected products with high yields (up to 98%) and good enantioselectivities (up to 93% ee). The absolute stereochemistry of the products has been determined by chemical correlation.

  DOI：

  10.1021/ol802509m

文献信息

• Enantioselective Zirconium-Catalyzed Friedel−Crafts Alkylation of Pyrrole with Trifluoromethyl Ketones
  作者：Gonzalo Blay、Isabel Fernández、Alicia Monleón、José R. Pedro、Carlos Vila

  DOI：10.1021/ol802509m

  日期：2009.1.15

  The first catalytic enantioselective Friedel-Crafts alkylation of pyrrole with 2,2,2-trifluoroacetophenones to give pyrroles with a trifluoromethyl-substituted tertiary alcohol moiety bearing a quaternary stereogenic center is described. The reaction is achieved in the presence of a 3,3'dibromo-BINOL-Zr(IV) complex to give the expected products with high yields (up to 98%) and good enantioselectivities (up to 93% ee). The absolute stereochemistry of the products has been determined by chemical correlation.