6-trifluoromethyl-N-phenyl-1H-benzo[d]imidazol-1-amine | 313485-97-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 6-trifluoromethyl-N-phenyl-1H-benzo[d]imidazol-1-amine
• 英文别名: 1-(phenylamino)-6-(trifluoromethyl)benzimidazole
• CAS: 313485-97-1
• 化学式: C₁₄H₁₀F₃N₃
• 分子量: 277.249
• InChiKey: GERAYTSCJYCYRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  29.85
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  6-trifluoromethyl-N-phenyl-1H-benzo[d]imidazol-1-amine 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 101.0h， 生成
  参考文献：
  名称：

  Syntheses and Properties of 1-Methyl-3-phenylaminobenzimidazolium Salts, Models of DNA Adducts of N7-Arylaminodeoxyguanosinium Salt

  摘要：

  When arylaminating carcinogens are administered to cells, they mainly generate the C8-arylamino-2'-deoxyguanosine adduct in DNA. A mechanism for this was proposed in which N7-arylaminated 2'-deoxyguanosine acts as an intermediate; however, it remained unclear whether this is actually the case. To elucidate the mechanisms involved in the generation of this adduct, a series of 5-substituted 1-methylbenzimidazole derivatives were used as models of the imidazole moiety of 2'-deoxyguanosine. Syntheses of a series of 5-substituted (CH3, H, F, CF3, or NO2) 1-methyl-3-phenylaminobenzimidazolium salts (7) and their related compounds were carried out, and the chemical characteristics of these products were examined. Keating compound 7 at 80 degreesC for 48 h in H2O/MeOH provided 5-substituted 1-methyl-2-oxo-2,3-dihydrobenzimidazoles but only when this compound contained a CF3 or NO2 substituent. Compound 7 decomposed in alkaline media, and its rate of decomposition increased when this compound had a stronger electron-withdrawing substituent. The product obtained under these conditions was 4-substituted N-1-methyl-2-phenylazoaniline. On the other hand, when 1-methyl-3-(4-nitrophenylamino)benzimidazolium salt was treated under the same conditions as described above, it generated, a demethylated product, 1-(4-nitrophenylamino)benzimidazole, when heated in H2O/MeOH and N-1-formyl-N-1-methyl-2-phenylazoaniline when treated in alkaline media. When the chemical characteristics of 3-phenylamino and 3-amino groups were compared using 3-substituted 1-methyl-5-(trifluoromethyl)benzimidazole the 3-phenylamino derivative was found to be more reactive.

  DOI：

  10.1021/tx0000724
• 作为产物：
  描述：

  N-(2-nitro-4-(trifluoromethyl)phenyl)acetamide 在 palladium on activated charcoal 盐酸 、 氢氧化钾 、 氢气 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 16.25h， 生成 6-trifluoromethyl-N-phenyl-1H-benzo[d]imidazol-1-amine
  参考文献：
  名称：

  Syntheses and Properties of 1-Methyl-3-phenylaminobenzimidazolium Salts, Models of DNA Adducts of N7-Arylaminodeoxyguanosinium Salt

  摘要：

  When arylaminating carcinogens are administered to cells, they mainly generate the C8-arylamino-2'-deoxyguanosine adduct in DNA. A mechanism for this was proposed in which N7-arylaminated 2'-deoxyguanosine acts as an intermediate; however, it remained unclear whether this is actually the case. To elucidate the mechanisms involved in the generation of this adduct, a series of 5-substituted 1-methylbenzimidazole derivatives were used as models of the imidazole moiety of 2'-deoxyguanosine. Syntheses of a series of 5-substituted (CH3, H, F, CF3, or NO2) 1-methyl-3-phenylaminobenzimidazolium salts (7) and their related compounds were carried out, and the chemical characteristics of these products were examined. Keating compound 7 at 80 degreesC for 48 h in H2O/MeOH provided 5-substituted 1-methyl-2-oxo-2,3-dihydrobenzimidazoles but only when this compound contained a CF3 or NO2 substituent. Compound 7 decomposed in alkaline media, and its rate of decomposition increased when this compound had a stronger electron-withdrawing substituent. The product obtained under these conditions was 4-substituted N-1-methyl-2-phenylazoaniline. On the other hand, when 1-methyl-3-(4-nitrophenylamino)benzimidazolium salt was treated under the same conditions as described above, it generated, a demethylated product, 1-(4-nitrophenylamino)benzimidazole, when heated in H2O/MeOH and N-1-formyl-N-1-methyl-2-phenylazoaniline when treated in alkaline media. When the chemical characteristics of 3-phenylamino and 3-amino groups were compared using 3-substituted 1-methyl-5-(trifluoromethyl)benzimidazole the 3-phenylamino derivative was found to be more reactive.

  DOI：

  10.1021/tx0000724

文献信息

• Palladium-catalyzed annulation of 2-(aryldiazenyl) aniline with dimethyl sulfoxide to access N-aryl-1H-benzo[d]imidazol-1-amine
  作者：Hepan Wang、Song Sun、Jiang Cheng

  DOI：10.1016/j.tetlet.2017.08.066

  日期：2017.10

  A palladium-catalyzed annulation of 2-(aryldiazenyl) aniline and dimethyl sulfoxide was developed to access N-aryl-1H-benzo[d]imidazol-1-amine in moderate to good yields. Activated by 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABSO), DMSO served as a “CH” fragment during this procedure. It represents a facile pathway leading to benzimidazoles.

  开发了钯催化的2-（芳基二氮烯基）苯胺和二甲基亚砜的环化反应，以中等至良好的产率获得N-芳基-1 H-苯并[ d ]咪唑-1-胺。DMSO被1,4-二氮杂双环[2.2.2]辛烷双（二氧化硫）加合物（DABSO）激活，在此过程中充当“ CH ”片段。它代表了导致苯并咪唑的简便途径。