1-phenyl-2-(trifluoromethyl)-1H-imidazole-5-carbaldehyde | 1357114-42-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-phenyl-2-(trifluoromethyl)-1H-imidazole-5-carbaldehyde
• 英文别名: 3-phenyl-2-(trifluoromethyl)imidazole-4-carbaldehyde
• CAS: 1357114-42-1
• 化学式: C₁₁H₇F₃N₂O
• 分子量: 240.185
• InChiKey: QBXKCXSNOYPOKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-phenyl-2-(trifluoromethyl)-1H-imidazole-5-carbaldehyde 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以84%的产率得到1-phenyl-2-(trifluoromethyl)-1H-imidazole
  参考文献：
  名称：

  Bi(iii)-catalyzed aminooxygenation of propargyl amidines to synthesize 2-fluoroalkyl imidazole-5-carbaldehydes and their decarbonylations

  摘要：

  Bi(iii)催化的氨氧化反应首次被用于合成2-氟烷基咪唑-5-甲醛，这些化合物在存在KOt-Bu的情况下可以高效脱羰基。

  DOI：

  10.1039/d0cc02143a
• 作为产物：
  描述：

  N-phenyl N’-propargyl 2-trifluoromethylamidine 在 N-碘代丁二酰亚胺 、 silver tetrafluoroborate 、 三苯基膦氯金 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 以98%的产率得到1-phenyl-2-(trifluoromethyl)-1H-imidazole-5-carbaldehyde
  参考文献：
  名称：

  Au（I）催化的氟化N'-芳基-N-炔丙基Am的分子内氢化胺化：合成2-氟烷基咪唑衍生物的温和条件

  摘要：

  开发了金（I）催化的2-氟烷基咪唑衍生物的合成。在金（I）的催化下，炔丙基am进行5 -exo-dig环化，得到2-氟烷基-5-甲基咪唑。同样，在NIS存在下获得2-氟烷基咪唑-5-甲醛。机理研究表明可能的过程和O 2衍生的羰基氧。

  DOI：

  10.1021/ol3000525

文献信息

• Au(I)-Catalyzed Intramolecular Hydroamination of the Fluorinated <i>N′</i>-Aryl-<i>N</i>-Propargyl Amidines: Mild Conditions for the Synthesis of 2-Fluoroalkyl Imidazole Derivatives
  作者：Shan Li、Zhengke Li、Yafen Yuan、Dongjie Peng、Yajun Li、Lisi Zhang、Yongming Wu

  DOI：10.1021/ol3000525

  日期：2012.2.17

  The gold(I)-catalyzed synthesis of 2-fluoroalkyl imidazole derivatives was developed. Catalyzed by gold(I), propargyl amidines underwent a 5-exo-dig cyclization to afford 2-fluoroalkyl-5-methyl imidazoles. Also, 2-fluoroalkyl imidazole-5-carbaldehydes were obtained in the presence of NIS. A mechanism investigation manifested the probable process and the carbonyl oxygen derived from O2.

  开发了金（I）催化的2-氟烷基咪唑衍生物的合成。在金（I）的催化下，炔丙基am进行5 -exo-dig环化，得到2-氟烷基-5-甲基咪唑。同样，在NIS存在下获得2-氟烷基咪唑-5-甲醛。机理研究表明可能的过程和O 2衍生的羰基氧。
• Gold(I)-Catalyzed Aminohalogenation of Fluorinated<i>N</i>′-Aryl-<i>N</i>-Propargyl Amidines for the Synthesis of Imidazole Derivatives under Mild Conditions
  作者：Shan Li、Zhengke Li、Yafen Yuan、Yajun Li、Lisi Zhang、Yongming Wu

  DOI：10.1002/chem.201202402

  日期：2013.1.21

  A procedure for the synthesis of fluorinated imidazole derivatives from propargyl amidines has been developed. Under gold(I) catalysis, propargyl amidines were converted into 5‐fluoromethyl imidazoles in the presence of Selectfluor through a cascade cyclization/fluorination process. In contrast, imidazole‐5‐carbaldehydes were obtained in high yields when N‐iodosuccinimide (NIS) was used as the halogenating

  已经开发了由炔丙基am合成氟化咪唑衍生物的方法。在金（I）催化下，在Selectfluor存在下，通过级联环化/氟化过程将炔丙基am转化为5-氟甲基咪唑。相反，当使用N-碘代琥珀酰亚胺（NIS）作为卤化剂时，可以高产率获得咪唑-5-甲醛。溶剂和光的极性对甲醛的形成有重大影响。这些转变显示出极好的功能组耐受性。具有吸电子基团的未氟化底物也进行了氨基卤代反应，从而以高收率得到了相应的产物。机理研究揭示了这些转变的一般途径。
• Divergent synthesis of 1,5-benzodiazepines and benzimidazoles via a BiCl3-catalyzed one-pot condensation–cyclization process
  作者：Jiaqi Sun、Shan Li、Meiqing Meng、Qiumei Xue、Xuliang Chen、Qiong Qin、Xiaofeng Liu、Qi Liu

  DOI：10.1007/s10593-023-03234-7

  日期：2023.8

  Catalyzed by BiCl3, aromatic o-diamines reacted with ketones efficiently to produce 1,5-benzodiazepines in good to excellent yields by condensation–cyclization reaction. Using aldehydes as substrates, mono- or disubstituted benzimidazoles were obtained as the final products. All reactions were carried out under mild reaction conditions and showed good functional group compatibility.

  在 BiCl 3催化下，芳香族邻二胺与酮有效反应，通过缩合环化反应以良好至优异的收率生成 1,5-苯二氮卓类化合物。使用醛作为底物，得到单或二取代的苯并咪唑作为最终产物。所有反应均在温和的反应条件下进行，表现出良好的官能团相容性。
• <i>N</i>-Iodosuccinimide-Mediated Synthesis of Benzo-Fused Bisimidazoles Enabled by a One-Pot Tandem Reaction of Fluorinated Propargyl Amidines
  作者：Shan Li、Lu Lei、Bin Feng、Xiaofeng Liu、Liqing Xian、Yajun Li

  DOI：10.1021/acs.joc.2c02379

  日期：——

  efficient tandem reaction between fluorinated propargyl amidines and aromatic o-diamines without any metal catalyst and additive under mild reaction conditions was developed for the synthesis of benzo-fused bisimidazoles in moderate to excellent yields. Preliminary mechanistic studies suggested that this reaction proceeded by an intermediate of secondary amine derived from 5-iodomethyl imidazole, and NIS

  在温和的反应条件下，在没有任何金属催化剂和添加剂的情况下，开发了 N-碘​​代琥珀酰亚胺 (NIS) 介导的氟化炔丙基脒和芳族邻二胺之间的发散和高效串联反应，以中等至优异的收率合成苯并稠合双咪唑。初步的机理研究表明，该反应是由 5-碘甲基咪唑衍生的仲胺中间体进行的，NIS 还起到了氧化试剂的作用，促进了苯并咪唑基序的形成。
• Iodine-mediated aminohalogenation-oxidation to synthesize 2-fluoroalkyl imidazole derivatives
  作者：Shan Li、Jian Liang、Xiaofeng Liu、Liqing Xian、Mingxu Du

  DOI：10.1007/s11696-020-01360-6

  日期：2021.3

  A simple and efficient method of iodine-mediated aminohalogenation-oxidation of fluorinated N’-propargyl amidines to synthesize 2-fluoroalkyl imidazole-5-carbaldehydes was developed. This method showed good functional group compatibility and wide substrate scope, as variety of substituted substrates proceeded smoothly to give the corresponding products in moderate to excellent yields. And this method was also suitable to unfluorinated substrates. Fluorinated allyl amidines used as starting materials, aminohalogenated products were obtained as the final products. Studies on the mechanism indicated that the carbonylation proceeded via 5-iodomethyl imidazole intermediate, and the carbonyl oxygen atom was demonstrated that originated from dioxygen.

  本研究开发了一种简单高效的碘介导的氨基卤化-氧化氟化 N'-丙炔基脒合成 2-氟烷基咪唑-5-羰基醛的方法。该方法具有良好的官能团兼容性和广泛的底物范围，各种取代的底物都能顺利合成相应的产物，收率从中等到极好。这种方法也适用于非氟化底物。以氟化烯丙基脒为起始原料，氨基卤化产物为最终产物。机理研究表明，羰基化反应是通过 5-iodomethyl imidazole 中间体进行的，羰基氧原子来源于二氧。