2,2,2-三氟-1-(1H-吲哚-3-基)乙-1-胺 | 126954-11-8

• 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
• 中文名称: 2,2,2-三氟-1-(1H-吲哚-3-基)乙-1-胺
• 英文名称: 2,2,2-trifluoro-1-(1H-indol-3-yl)ethylamine
• 英文别名: 1-(Indol-3-yl)-2,2,2-trifuoroethyl amine；3-(α-Aminotrifluoroethyl)indole；2,2,2-trifluoro-1-(1H-indol-3-yl)ethan-1-amine；2,2,2-trifluoro-1-(1H-indol-3-yl)ethanamine
• CAS: 126954-11-8
• 化学式: C₁₀H₉F₃N₂
• mdl: MFCD07777243
• 分子量: 214.19
• InChiKey: TZQBOSKCYLEGAX-UHFFFAOYSA-N

物化性质

• 熔点：
  145-147 °C(Solv: hexane (110-54-3))
• 沸点：
  337.6±42.0 °C(Predicted)
• 密度：
  1.377±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  41.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-(α-Carbomethoxy-α-trifluoroacetamidotrifluoroethyl)indole 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 8.0h， 以61%的产率得到2,2,2-三氟-1-(1H-吲哚-3-基)乙-1-胺
  参考文献：
  名称：

  The C-alkylation of some heteroaromatic compounds by the trifluoroacetylimine of methyl trifluoropyruvate

  摘要：

  DOI：

  10.1007/bf00957802

文献信息

• BF₃-Promoted Aromatic Substitution of<i>N</i>-Alkyl<i>α</i>-Trifluoromethylated Imine: Facile Synthesis of 1-Aryl-2,2,2-trifluoroethylamines
  作者：Yuefa Gong、Katsuya Kato、Hiroshi Kimoto

  DOI：10.1246/bcsj.75.2637

  日期：2002.12

  The aromatic substitution of three representative N-alkyl trifluoromethyl imines 1a–c (R: a, benzyl; b, benzhydryl; c, methyl), obtained from primary alkyl amines and trifluoroacetaldehyde ethyl hemiacetal, was used to investigate the preparation of 1-aryl-2,2,2-trifluoroethylamines. In the presence of BF3·OEt2, the reaction of imine 1 with various aromatic compounds proceeded smoothly at room temperature

  从伯烷基胺和三氟乙醛乙基半缩醛中获得的三种代表性 N-烷基三氟甲基亚胺 1a-c（R：a，苄基；b，二苯甲基；c，甲基）的芳族取代用于研究 1-芳基的制备-2,2,2-三氟乙胺。在BF3·OEt2的存在下，亚胺1与各种芳香族化合物在室温下反应顺利进行，得到了中高产率的N-烷基-1-芳基-2,2,2-三氟乙胺。此外，通过在盐酸中水解或通过钯催化的氢解，成功地区域选择性去除 N-苄基和 N-二苯甲基。
• Convenient preparation of 1-(indol-3-yl)-2,2,2-trifluoroethylamines via Friedel–Crafts reaction of α-trifluoroacetaldehyde hemiaminal
  作者：Yuefa Gong、Katsuya Kato

  DOI：10.1016/s0022-1139(00)00407-3

  日期：2001.3

  Electrophilic substitution of indole with trifluoroacetaldehyde hemiaminals 1a-f, prepared from primary amines and trifluoroacetaldehyde ethyl hemiacetal (TFAE), proceeds readily in the presence of Lewis acids. Formation of N-alkyl 1-(indol-3-yl)-2,2,2-trifluoroethylamines (2) is preferred in the presence of BF3, but yield of 2,2,2-trifluoroethyl alcohol (3) markedly increases when ZnI2 is used. A stereochemistry study clearly showed that ethylamines 2e and 2f are produced with high diastereoselective excess when the optically active hemiaminals 1e and 1f are used. (C) 2001 Elsevier Science B.V. All rights reserved.
• Convenient synthesis of α-trifluoromethyl amines via aminofluoroalkylation of arenes with N-trimethylsilyl α-trifluoroacetaldehyde hemiaminal
  作者：Yuefa Gong、Katsuya Kato

  DOI：10.1016/s0022-1139(02)00044-1

  日期：2002.8

  Aminofluoroalkylation of various heteroarenes or substituted benzenes with the N-trimethylsilyl hemiaminals, prepared from 1,1,1,3,3,3-hexamethyldisilazane and gaseous trifluoroacetaldehyde, smoothly underwent at room temperature in the presence of a Lewis acid. [(1-Aryl-2,2,2-trifluoro)ethyl]amines or bis[(1-aryl-2,2,2-trifluoro)ethyl]amines were afforded in moderate to high yields. (C) 2002 Published by Elsevier Science B.V.
• OSIPOV, S. N.;CHKANIKOV, N. D.;SHKLYAEV, YU. V.;KOLOMIETS, A. F.;FOKIN, A+, IZV. AN CCCP. CEP. XIM.,(1989) N, S. 2131-2134
  作者：OSIPOV, S. N.、CHKANIKOV, N. D.、SHKLYAEV, YU. V.、KOLOMIETS, A. F.、FOKIN, A+

  DOI：——

  日期：——
• The C-alkylation of some heteroaromatic compounds by the trifluoroacetylimine of methyl trifluoropyruvate
  作者：S. N. Osipov、N. D. Chkanikov、Yu. V. Shklyaev、A. F. Kolomiets、A. V. Fokin

  DOI：10.1007/bf00957802

  日期：1989.9