1-(trifluoromethyl)tetrahydroazepine | 1146222-77-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吖庚因类
• 英文名称: 1-(trifluoromethyl)tetrahydroazepine
• 英文别名: 7-(trifluoromethyl)-3,4,5,6-tetrahydro-2H-azepine
• CAS: 1146222-77-6
• 化学式: C₇H₁₀F₃N
• 分子量: 165.158
• InChiKey: GJQDOUIPGLRQDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(trifluoromethyl)tetrahydroazepine 在 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 以82%的产率得到2-(trifluoromethyl)azepane hydrochloride
  参考文献：
  名称：

  实用合成α-全氟烷基环状亚胺和胺

  摘要：

  对于α-CF的制备方便和简单的方法3和α-C 2 ˚F 5取代的吡咯啉，四氢吡啶，tetrahydroazepine进行说明。N-保护的环酰胺与全氟羧酸的酯的克莱森缩合，然后在酸性介质中脱保护和脱羧，得到所需的产物。这些亚胺的还原允许获得5-，6-和7-元环胺用α-CF 3或α-C 2 ˚F 5基团以良好至中度的总产率。 氟-氮杂环-α-多氟烷基亚胺-还原

  DOI：

  10.1055/s-0029-1217104
• 作为产物：
  描述：

  3-(trifluoroacetyl)azepan-2-one 在 盐酸 、 sodium hydroxide 作用下， 生成 1-(trifluoromethyl)tetrahydroazepine
  参考文献：
  名称：

  Friedel–Crafts alkylation of natural amino acid-derived pyrroles with CF3-substituted cyclic imines

  摘要：

  Natural amino acid-derived ethyl 2-(1-pyrrolyl)alkanoates react with 2-trifluoromethyl-1-azacycloalkenes selectivity at the P-position of the pyrrole moiety to afford ethyl 2[3-(1-trifluoromethyl-2-azacycloalkyl)pyrrol-1-yl]alkanoates.

  DOI：

  10.1016/j.mencom.2013.03.013

文献信息

• Highly β-Regioselective Friedel-Crafts Aminoalkylation of Pyrroles with Cyclic Perfluoroalkylated Imines
  作者：Olga I. Shmatova、Nikolay E. Shevchenko、Elisabeth S. Balenkova、Gerd-Volker Röschenthaler、Valentine G. Nenajdenko

  DOI：10.1002/ejoc.201201725

  日期：2013.5

  A Friedel–Crafts-type alkylation reaction was studied between various pyrroles and α-polyfluoroalkylated cyclic imines that were activated by Lewis acids. The reaction proceeded under mild conditions and provided a high yielding synthesis of α-CF3-substituted pyrrolidines and piperidines as well as seven-membered analogues that contained a pyrrole ring. The unpredictably high β-selectivity for the

  研究了各种吡咯和由路易斯酸活化的 α-多氟烷基化环状亚胺之间的 Friedel-Crafts 型烷基化反应。该反应在温和的条件下进行，并提供了 α-CF3-取代的吡咯烷和哌啶以及含有吡咯环的七元类似物的高产合成。由于热力学控制的亲电取代反应，观察到 1H-吡咯和 N-取代的吡咯的氨基烷基化的不可预测的高β-选择性。计算数据与实验结果完全一致，这证实了观察到的区域选择性，这是由于含有 α-三氟甲基取代吡咯烷、哌啶和氮杂环庚烷环的 β 取代吡咯的能量较低。
• Efficient Multicomponent Synthesis of α-Trifluoromethyl Proline, Homoproline, and Azepan Carboxylic Acid Dipeptides
  作者：Gerd-V. Röschenthaler、Valentine Nenajdenko、Anton Gulevich、Nikolay Shevchenko、Elisabeth Balenkova

  DOI：10.1055/s-0028-1087529

  日期：2009.2

  Cyclic imines bearing CF 3 and C 2 F 5 group were successfully used for the first Ugi multicomponent synthesis of polyfluoroalkyl-substituted proline, homoproline, and azepan carboxylic acid derivatives. Based on the suggested reaction the first synthesis of dipeptides containing α-CF 3 cyclic amino acids residue was described. The scope and limitations of the approach are discussed.

  带有CF 3 和C 2 F 5 基团的环状亚胺已成功用于多氟烷基取代的脯氨酸、高脯氨酸和氮杂环庚烷羧酸衍生物的首次Ugi多组分合成。基于所建议的反应，描述了含有α-CF 3 环状氨基酸残基的二肽的第一次合成。讨论了该方法的范围和局限性。
• Enantioselective Synthesis of Thiazole-Derived α-Perfluoroalkylated 5-7-Membered Amines
  作者：Natalia G. Voznesenskaia、Olga I. Shmatova、Mikhail M. Ilyin、Mikhail M. Ilyin、Valentine G. Nenajdenko

  DOI：10.1002/ejoc.201801845

  日期：2019.3.7

  Enantioselective synthesis of thiazole‐containing α‐perfluoroalkylated cyclic amines was elaborated. Enantioselective Strecker hydrocyanation followed by the reaction with hydrogen sulfide resulted in highly efficient formation of the corresponding thioamides. Finally, Hantzsch reactions provided access to a family of fluorinated analogues of natural products.

  详细阐述了含噻唑的α-全氟烷基化环胺的对映选择性合成。对映选择性斯特雷克氢氰化反应，然后与硫化氢反应，可高效形成相应的硫代酰胺。最后，汉茨反应使人们可以接触到一系列天然产物的氟化类似物。
• Pictet–Spengler Synthesis of Perfluoroalkylated Tetrahydro-γ-carbolines and Tetrahydropyrrolopyrazines
  作者：Natalia G. Voznesenskaia、Olga I. Shmatova、Valentine G. Nenajdenko

  DOI：10.1055/s-0039-1690729

  日期：2020.1

  A new method for the synthesis of perfluoroalkylated derivatives of γ-carboline and pyrrolopyrazine was elaborated. Pictet–Spengler reaction of isotryptamine and 2-(pyrrol-1-yl)ethanamine with trifluoromethylated carbonyls and 2-perfluoroalkyl-substituted five-, six-, and seven-membered cyclic imines was studied. It was found that this approach opens efficient access to a family of alkaloid-like compounds

  阐述了合成γ-咔啉和吡咯并吡嗪全氟烷基化衍生物的新方法。研究了异色胺和2-（吡咯-1-基）乙胺与三氟甲基化羰基和2-全氟烷基取代的五元，六元和七元亚胺的Pictet-Spengler反应。已经发现，该方法打开了对结构中带有CF 3或C 2 F 5基团的生物碱样化合物家族的有效访问的途径。在与2-全氟烷基取代的环亚胺进行iso-Pictet-Spengler反应的情况下，制备了一系列带有氨基烷基的γ-咔啉。
• Tetrazole-Substituted Five, Six, and Seven-Membered Cyclic Amines Bearing Perfluoroalkyl Groups - Efficient Synthesis by Azido-Ugi Reaction
  作者：Olga I. Shmatova、Valentine G. Nenajdenko

  DOI：10.1002/ejoc.201300861

  日期：2013.10

  azido-Ugi reactions was studied. It was shown that the reaction allows access to five-, six- and seven-membered perfluoroalkylated cyclic amines connected to a tetrazole ring. The scope and limitations of this approach are discussed. When benzyl isocyanide was used in the azido-Ugi reaction, it was shown that the tetrazole products could easily be debenzylated by catalytic hydrogenation to form 1H-tetrazoles

  研究了全氟烷基化环亚胺在叠氮基-Ugi反应中的应用。结果表明，该反应允许获得与四唑环相连的五元、六元和七元全氟烷基化环胺。讨论了这种方法的范围和局限性。当在叠氮基-Ugi 反应中使用苄基异氰化物时，表明四唑产物可以很容易地通过催化氢化脱苄基，以优异的产率形成 1H-四唑。