(R)-4-(3,5-bis(trifluoromethyl)phenyl)-4-(5-chloro-1H-indol-3-yl)-1,1,1-trifluorobutan-2-one | 1245186-64-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-4-(3,5-bis(trifluoromethyl)phenyl)-4-(5-chloro-1H-indol-3-yl)-1,1,1-trifluorobutan-2-one
• CAS: 1245186-64-4
• 化学式: C₂₀H₁₁ClF₉NO
• 分子量: 487.752
• InChiKey: PEAJDRIKDCYRMQ-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.51
• 重原子数：
  32.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  32.86
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  4-[3,5-Bis(trifluoromethyl)phenyl]-1,1,1-trifluorobut-3-en-2-one 、 5-氯吲哚 在 (S)-3,3'-bis(9-anthracenyl)-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate 作用下， 以 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 72.0h， 生成 (R)-4-(3,5-bis(trifluoromethyl)phenyl)-4-(5-chloro-1H-indol-3-yl)-1,1,1-trifluorobutan-2-one 、
  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