methyl 3-[(2S)-3-ethoxy-1,1,1-trifluoro-2-hydroxy-3-oxopropan-2-yl]-1H-indole-4-carboxylate | 1215299-21-0

• 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: methyl 3-[(2S)-3-ethoxy-1,1,1-trifluoro-2-hydroxy-3-oxopropan-2-yl]-1H-indole-4-carboxylate
• CAS: 1215299-21-0
• 化学式: C₁₅H₁₄F₃NO₅
• 分子量: 345.275
• InChiKey: MTQVBLYFHLIUCD-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  88.6
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  吲哚-4-羧酸甲酯 、 三氟乙酸乙酯 在 CSCS 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以86%的产率得到
  参考文献：
  名称：

  Enhanced efficiency of recyclable C3-symmetric cinchonine-squaramides in the asymmetric Friedel–Crafts reaction of indoles with alkyl trifluoropyruvate

  摘要：

  The highly enantioselective Friedel-Crafts reaction of indoles with trifluoropyruvate catalyzed by a C-3-symmetric cinchonine-squaramide is reported. A wide variety of trifluoromethylated indole derivatives were obtained in high yields and with excellent enantioselectivities (99% and up to > 99% ee). Moreover the C-3 catalyst can be easily recovered and was used five times. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.08.015

文献信息

• Enhanced efficiency of recyclable C3-symmetric cinchonine-squaramides in the asymmetric Friedel–Crafts reaction of indoles with alkyl trifluoropyruvate
  作者：Xin Han、Bin Liu、Hai-Bing Zhou、Chune Dong

  DOI：10.1016/j.tetasy.2012.08.015

  日期：2012.10

  The highly enantioselective Friedel-Crafts reaction of indoles with trifluoropyruvate catalyzed by a C-3-symmetric cinchonine-squaramide is reported. A wide variety of trifluoromethylated indole derivatives were obtained in high yields and with excellent enantioselectivities (99% and up to > 99% ee). Moreover the C-3 catalyst can be easily recovered and was used five times. (C) 2012 Elsevier Ltd. All rights reserved.