1,2-Dipropylbenzimidazole | 476324-79-5

• 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: 1,2-Dipropylbenzimidazole
• CAS: 476324-79-5
• 化学式: C₁₃H₁₈N₂
• mdl: 36.4606
• 分子量: 202.299
• InChiKey: RFQGGISTRHNFKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  正丁醛 、 邻苯二胺 在 mesoporous mixed metal oxide nanocrystals of Al₂O₃-Fe₂O₃, Al₂O₃-V₂O₅, Al₂O₃-CuO 作用下， 反应 0.01h， 以89%的产率得到1,2-Dipropylbenzimidazole
  参考文献：
  名称：

  Mesoporous mixed metal oxide nanocrystals: Efficient and recyclable heterogeneous catalysts for the synthesis of 1,2-disubstituted benzimidazoles and 2-substituted benzothiazoles

  摘要：

  Present communication elicits the use of mesoporous mixed metal oxide nanocrystals of Al2O3-Fe2O3. Al2O3-V2O5 and Al2O3-CuO as heterogeneous catalysts for the preparation of series of medicinally significant 1,2-disubstituted benzimidazoles and 2-substituted benzothiazoles. These nanocrystalline catalysts exhibited remarkable catalytic activity with a high substrate to catalyst weight ratio (20:1) to achieve the synthetic targets in the range of yield 81-96%. The solvent-free microwave assisted synthesis of these compounds was an advantageous way which resulted in excellent yields in much lesser time (0.75-1.5 min) in comparison to conventional heating. The use of catalyst in eco-friendly green protocol and its reusability up to four cycles with similar catalytic response are the unique features of the heterogeneous catalysis. This protocol provided greater selectivity, cost-efficiency, clean reaction profiles, simple work-up procedure and high yields. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2011.03.027

文献信息

• An Efficient Synthesis of Benzimidazoles via Palladium-Catalyzed Amine Exchange Reaction from Trialkylamines to o-Phenylenediamine in an Aqueous Medium
  作者：Ngoc Thang Tran、Chan Sik Cho

  DOI：10.5012/bkcs.2012.33.12.4188

  日期：2012.12.20

  known as amine exchange reaction (amine scrambling reaction) and used for the synthesis of unsymmetrical amines and N-heterocycles and the study of the metabolism of amines. During the course of our studies directed towards transition metal-catalyzed C-N bond activation of alkylamines, we developed an alkyl (or alkanol) group transfer from alkylamines (or alkanolamines) to Natom of anilines as well

  过渡金属催化烷基胺之间的烷基转移被称为胺交换反应（amine scrambling reaction），用于不对称胺和N-杂环的合成以及胺代谢的研究。在我们针对过渡金属催化的烷基胺的 CN 键活化的研究过程中，我们开发了从烷基胺（或烷醇胺）到苯胺的 Natom 以及酮的 α-碳的烷基（或烷醇）基团转移，从而导致酮的区域选择性α-烷基化。在所采用的反应条件下，前一种转移最终导致吲哚和喹啉。然而，除了我们的发现之外，仅已知少数使用这种胺交换反应合成 N-杂环的例子。众所周知，氢嘧啶，咪唑烷和咪唑可以通过钯催化的二胺和烷基胺之间的分子间胺交换反应形成。发现二胺通过钌催化的分子内胺交换反应环化为吡咯烷、哌啶和氮杂环丙烷。另一方面，与本报告有关，Murahashi 等人。据报道，N-甲基苄胺与邻苯二胺在 Pd/C 存在下反应生成 2-苯基苯并咪唑和 1-苄基-2-苯基苯并咪唑，产率分别为 37% 和