(R)-2,2,2-trifluoro-1-(1H-indol-2-yl)-1-phenylethanol | 1096376-03-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (R)-2,2,2-trifluoro-1-(1H-indol-2-yl)-1-phenylethanol
• 英文别名: (R)-1-Phenyl-1-(1H-indole-2-yl)-2,2,2-trifluoroethanol；(1R)-2,2,2-trifluoro-1-(1H-indol-2-yl)-1-phenylethanol
• CAS: 1096376-03-2
• 化学式: C₁₆H₁₂F₃NO
• 分子量: 291.273
• InChiKey: WPDWIRGTRSQOQU-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  36
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 对苯醌 作用下， 生成 (R)-2,2,2-trifluoro-1-(1H-indol-2-yl)-1-phenylethanol
  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

• Chiral Brønsted Acid-Catalyzed Enantioselective Friedel-Crafts Reaction of 4,7-Dihydroindoles with Trifluoromethyl Ketones
  作者：Teng Wang、Guang-Wu Zhang、Yuou Teng、Jing Nie、Yan Zheng、Jun-An Ma

  DOI：10.1002/adsc.201000510

  日期：2010.11.2

  In the presence of chiral phosphoric acid, an enantioselective Friedel–Crafts reaction of 4,7-dihydroindoles with aromatic trifluoromethyl ketones and ethyl 4,4,4-trifluoroacetoacetate has been realized. A series of 2-substituted 4,7-dihydroindoles with a trifluoromethylated tertiary alcohol moiety were obtained in 45–95% yields with 60–93% ee. Furthermore, 2-functionalized indole derivatives could

  在手性磷酸的存在下，已经实现了4,7-二氢吲哚与芳族三氟甲基酮和4,4,4-三氟乙酰乙酸乙酯的对映选择性Friedel-Crafts反应。以45–95％的收率和60–93％ee的产率获得了一系列带有三氟甲基化叔醇部分的2-取代的4,7-二氢吲哚。此外，可以通过一锅法制备2-官能化的吲哚衍生物。
• 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.