N-methyl-N-phenyl-1H-benzo[d]imidazol-2-amine | 1332624-60-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-methyl-N-phenyl-1H-benzo[d]imidazol-2-amine
• 英文别名: N-methyl-N-phenyl-1H-benzimidazol-2-amine
• CAS: 1332624-60-8
• 化学式: C₁₄H₁₃N₃
• 分子量: 223.277
• InChiKey: CRTDZDMHMZLKHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  31.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-己炔 、 N-methyl-N-phenyl-1H-benzo[d]imidazol-2-amine 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 silver(I) acetate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以18%的产率得到(E)-12-ethyl-5-methyl-12-(prop-1-en-1-yl)-5,12-dihydrobenzo[4,5]imidazo[2,1-b]quinazoline
  参考文献：
  名称：

  Rh(III)-Catalyzed [5 + 2] Oxidative Annulation of Cyclic Arylguanidines and Alkynes to 1,3-Benzodiazepines. A Striking Mechanistic Proposal from DFT

  摘要：

  A novel and mild Rh(III)-catalyzed [5 + 2] oxidative annulation between cyclic arylguanidines and alkynes efficiently affords 1,3-benzodiazepines (pentacyclic guanidines). The use of O-2 as the sole oxidant in place of commonly used metal oxidants such as AgOAc clearly improves the efficiency of the oxidative annulation process. The mechanism of the cycloaddition most likely involves the formation of an eight-membered rhodacycle. DFT calculations support a striking mechanistic proposal for the [5 + 2] oxidative annulation.

  DOI：

  10.1021/acs.orglett.9b00354
• 作为产物：
  描述：

  N-甲基苯胺 在 正丁基锂 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 N-methyl-N-phenyl-1H-benzo[d]imidazol-2-amine
  参考文献：
  名称：

  Rh(III)-Catalyzed [5 + 2] Oxidative Annulation of Cyclic Arylguanidines and Alkynes to 1,3-Benzodiazepines. A Striking Mechanistic Proposal from DFT

  摘要：

  A novel and mild Rh(III)-catalyzed [5 + 2] oxidative annulation between cyclic arylguanidines and alkynes efficiently affords 1,3-benzodiazepines (pentacyclic guanidines). The use of O-2 as the sole oxidant in place of commonly used metal oxidants such as AgOAc clearly improves the efficiency of the oxidative annulation process. The mechanism of the cycloaddition most likely involves the formation of an eight-membered rhodacycle. DFT calculations support a striking mechanistic proposal for the [5 + 2] oxidative annulation.

  DOI：

  10.1021/acs.orglett.9b00354

文献信息

• Direct, Metal-Free Amination of Heterocyclic Amides/Ureas with NH-Heterocycles and N-Substituted Anilines in POCl₃
  作者：Xiaohu Deng、Armin Roessler、Ivana Brdar、Roger Faessler、Jiejun Wu、Zachary S. Sales、Neelakandha S. Mani

  DOI：10.1021/jo201425q

  日期：2011.10.21

  A POCl3-mediated, direct amination reaction of heterocyclic amides/ureas with NH-heterocycles or N-substituted anilines is described. Compared to the existing methods, this operationally simple protocol provides unique reactivity and functional group compatibility because of the metal-free, acidic reaction conditions. The yields are generally excellent.

  描述了POCl 3介导的杂环酰胺/脲与NH-杂环或N-取代的苯胺的直接胺化反应。与现有方法相比，该操作简单的协议由于无金属的酸性反应条件，提供了独特的反应性和官能团兼容性。产量通常是极好的。
• Assembly of fluorinated benzodiazepines <i>via</i> Rh(<scp>iii</scp>)-catalysed [5+2] annulation of <i>N</i>-benzo[<i>d</i>]imidazole indolines with 2,2-difluorovinyl tosylate
  作者：Fu-Xiaomin Liu、Weijie Chen、Lei Ma、Kui Cheng、Zhi Zhou、Wei Yi

  DOI：10.1039/d3nj01544k

  日期：——

  an unusual 1,2-regioselectivity for the chemodivergent construction of monofluorinated and gem-difluorinated benzodiazepines, which are defined as potent anti-tumor agents against different cancer cell lines. In general, this work provides a powerful complement to both C–H activation chemistry and anti-tumor lead discovery.

  在此，我们实现了一种高效且溶剂可调的Rh( III )催化的N-苯并[ d ]咪唑二氢吲哚与2,2-二氟乙烯基甲苯磺酸酯的[5+2]成环反应，该反应呈现出不寻常的1,2-区域选择性。单氟化和双氟化苯二氮卓类药物的化学发散结构，被定义为针对不同癌细胞系的有效抗肿瘤剂。总的来说，这项工作为 C-H 活化化学和抗肿瘤先导化合物的发现提供了强有力的补充。
• 4H-IMIDAZO[1,2-A]IMIDAZOLES FOR ELECTRONIC APPLICATIONS
  申请人：UDC Ireland Limited

  公开号：EP3640252A1

  公开（公告）日：2020-04-22

  The present invention relates to compounds of formula (I), a process for their production and their use in electronic devices, especially electroluminescent devices. When used as host material for phosphorescent emitters in electroluminescent devices, the compounds of formula (I) may provide improved efficiency, stability, manufacturability, or spectral characteristics of electroluminescent devices.

  本发明涉及式（I）化合物、其生产工艺及其在电子设备，尤其是电致发光设备中的应用。当用作电致发光器件中磷光发光体的主材料时，式（I）化合物可提高电致发光器件的效率、稳定性、可制造性或光谱特性。
• N-Heterocyclyl-4-piperidinamines, methods for their preparation, pharmaceutical compositions comprising them, intermediates therefor, and method for the preparation of the intermediates
  申请人：JANSSEN PHARMACEUTICA N.V.

  公开号：EP0005318B1

  公开（公告）日：1982-01-06
• US4219559A
  申请人：——

  公开号：US4219559A

  公开（公告）日：1980-08-26