(2S,4R)-1,1,1-trifluoro-4-(1H-indol-3-yl)-4-phenylbutan-2-ol | 1245186-69-9

• 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: (2S,4R)-1,1,1-trifluoro-4-(1H-indol-3-yl)-4-phenylbutan-2-ol
• CAS: 1245186-69-9
• 化学式: C₁₈H₁₆F₃NO
• 分子量: 319.326
• InChiKey: JWZQYONNAXFXLA-PBHICJAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.61
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  36.02
• 氢给体数：
  2.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  1,1,1-trifluoro-4-(1H-indol-3-yl)-4-phenyl-butan-2-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 (2S,4R)-1,1,1-trifluoro-4-(1H-indol-3-yl)-4-phenylbutan-2-ol 、 (2R,4R)-1,1,1-trifluoro-4-(1H-indol-3-yl)-4-phenylbutan-2-ol
  参考文献：
  名称：

  Chiral Brønsted acid-catalyzed regio- and enantioselective arylation of α,β-unsaturated trifluoromethyl ketones

  摘要：

  The interesting examples of chiral phosphoric acid-catalyzed regio- and enantioselective arylation of alpha,beta-unsaturated trifluoromethyl ketones were reported. The reaction proceeded well and the desired products were obtained in good yields (up to 99%) with moderate to good enantioselectivities (up to 88% ee). Several desired products were obtained with excellent optical purities after a single recrystallization. Subsequent reduction of enantiopure products with NaBH4 afforded two diastereomers of chiral trifluoromethyl-substituted secondary alcohols with high enantioselectivities (98% ee). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.06.132