1,1,1-trifluoro-4-(1H-indol-3-yl)-4-phenyl-butan-2-one | 1245186-43-9

• 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: 1,1,1-trifluoro-4-(1H-indol-3-yl)-4-phenyl-butan-2-one
• 英文别名: (4R)-1,1,1-trifluoro-4-(1H-indol-3-yl)-4-phenylbutan-2-one
• CAS: 1245186-43-9
• 化学式: C₁₈H₁₄F₃NO
• 分子量: 317.31
• InChiKey: VDTWVDOHRUVFAU-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  吲哚 、 1,1,1-三氟-4-苯基丁-3-烯-2-酮 在 (S,S)-2,6-双(4-异丙基-2-恶唑啉-2-基)吡啶 、 dysprosium(III) trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 1,1,1-trifluoro-4-(1H-indol-3-yl)-4-phenyl-butan-2-one 、 1,1,1-trifluoro-4-(1H-indol-3-yl)-4-phenyl-butan-2-one
  参考文献：
  名称：

  Dy（OTf）3 / Pybox催化的具有α，β-不饱和三氟甲基酮的吲哚对映选择性Friedel-Crafts烷基化反应

  摘要：

  用α，β-不饱和三氟甲基酮对吲哚进行的首个催化对映选择性Friedel-Crafts烷基化反应已经完成。该反应是在Dy（OTf）3 / Pybox络合物存在下完成的，以高收率（最高99％）和良好的对映选择性（最高86％ee）生产出所需的产物。通过X射线分析确定所得加合物的绝对立体化学。

  DOI：

  10.1016/j.tetlet.2010.02.121

文献信息

• Dy(OTf)3/Pybox-catalyzed enantioselective Friedel–Crafts alkylation of indoles with α,β-unsaturated trifluoromethyl ketones
  作者：Shigeru Sasaki、Takayasu Yamauchi、Kimio Higashiyama

  DOI：10.1016/j.tetlet.2010.02.121

  日期：2010.4

  The first catalytic enantioselective Friedel–Crafts alkylation of indoles with α,β-unsaturated trifluoromethyl ketones has been accomplished. The reaction was achieved in the presence of the Dy(OTf)3/Pybox complex, producing the desired products in high yields (up to 99%) with good enantioselectivities (up to 86% ee). The absolute stereochemistry of the resulting adducts was determined by X-ray analysis

  用α，β-不饱和三氟甲基酮对吲哚进行的首个催化对映选择性Friedel-Crafts烷基化反应已经完成。该反应是在Dy（OTf）3 / Pybox络合物存在下完成的，以高收率（最高99％）和良好的对映选择性（最高86％ee）生产出所需的产物。通过X射线分析确定所得加合物的绝对立体化学。
• Chiral Brønsted acid-catalyzed regio- and enantioselective arylation of α,β-unsaturated trifluoromethyl ketones
  作者：Zeng-kai Pei、Yan Zheng、Jing Nie、Jun-An Ma

  DOI：10.1016/j.tetlet.2010.06.132

  日期：2010.9

  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.