N-butyl-1H-benzo[d]imidazole-2-carboxamide | 74527-55-2

• 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: N-butyl-1H-benzo[d]imidazole-2-carboxamide
• 英文别名: N-Butyl-2-benzimidazol-carbonsaeure-amid；1H-benzoimidazole-2-carboxylic acid butylamide；1H-benzimidazole-2-carboxylic acid butylamide；1H-Benzimidazol-2-carbonsaeure-butylamid；(Butylcarbamoyl)benzimidazol；N-butyl-1H-benzimidazole-2-carboxamide
• CAS: 74527-55-2
• 化学式: C₁₂H₁₅N₃O
• mdl: MFCD24389925
• 分子量: 217.271
• InChiKey: UDSGQSQCZMXMPT-UHFFFAOYSA-N

物化性质

• 熔点：
  175-177 °C
• 密度：
  1.174±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  57.8
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-butyl-1H-benzo[d]imidazole-2-carboxamide 在 硫酸 、 氢溴酸 、 硝酸 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 (5-nitro-1H-benzimidazol-2-yl)-(4-benzyl-piperidin-1-yl)-methanone
  参考文献：
  名称：

  Benzimidazole-2-carboxamides as novel NR2B selective NMDA receptor antagonists

  摘要：

  A novel series of benzimidazole-2-carboxamide derivatives was prepared and identified as NR2B selective NMDA receptor antagonists. The influence of some structural elements, like H-bond donor groups placed on the benzimidazole skeleton and the substitution pattern of the piperidine ring, on the biological activity was studied. Compound 6a showed excellent analgetic activity in the mouse formalin test following po administration. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.06.002
• 作为产物：
  描述：

  ethyl 2-((2-nitrophenyl)amino)-2-oxoacetate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 10.17h， 生成 N-butyl-1H-benzo[d]imidazole-2-carboxamide
  参考文献：
  名称：

  Benzimidazole-2-carboxamides as novel NR2B selective NMDA receptor antagonists

  摘要：

  A novel series of benzimidazole-2-carboxamide derivatives was prepared and identified as NR2B selective NMDA receptor antagonists. The influence of some structural elements, like H-bond donor groups placed on the benzimidazole skeleton and the substitution pattern of the piperidine ring, on the biological activity was studied. Compound 6a showed excellent analgetic activity in the mouse formalin test following po administration. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.06.002

文献信息

• Ruthenium-catalyzed oxidative decyanative cross-coupling of acetonitriles with amines in air: a general access to primary to tertiary amides under mild conditions
  作者：Yuguang Wang、Zhongli Wu、Qin Li、Bingchun Zhu、Lei Yu

  DOI：10.1039/c7cy00761b

  日期：——

  Catalyzed by Ru and in the presence of air and nucleophiles such as amines or ammonia, activation of the C–CN bond could be easily achieved under mild conditions to produce primary to tertiary amides in good to excellent yields. The use of accessible and functional-group-tolerant starting materials, a cheap, low-loading and recyclable catalyst, ligand-free conditions and excellent product yields are

  在钌的催化下，在空气和亲核试剂（例如胺或氨）的存在下，在温和条件下可以很容易地实现C-CN键的活化，从而以良好或优异的产率生产伯酰胺至叔酰胺。该方法的优点是使用易接近且具有功能基团耐受性的起始原料，廉价，低载和可循环使用的催化剂，无配体的条件以及优异的产物收率。而且，与Ritter反应和水合方法相比，该新颖反应具有更广泛的应用范围。
• Synthesis of benzimidazole-2-carboxylic acid amides from o-phenylenediamine and oxamic acid esters
  作者：P. A. Petyunin、Abdul Malek Choudry

  DOI：10.1007/bf00526091

  日期：1982.5
• Agents for preserving technical materials against insects
  申请人：NIHON BAYER AGROCHEM K.K.

  公开号：EP0632034B1

  公开（公告）日：1998-08-19
• PETYUNIN, P. A.;ABDUL, MALEK, CHOUDRI, XIMIYA GETEROTSIKL. SOEDIN., 1982, N 5, 684-686
  作者：PETYUNIN, P. A.、ABDUL, MALEK, CHOUDRI

  DOI：——

  日期：——
• Benzimidazole-2-carboxamides as novel NR2B selective NMDA receptor antagonists
  作者：István Borza、Sándor Kolok、Anikó Gere、József Nagy、László Fodor、Kornél Galgóczy、József Fetter、Ferenc Bertha、Béla Ágai、Csilla Horváth、Sándor Farkas、György Domány

  DOI：10.1016/j.bmcl.2006.06.002

  日期：2006.9

  A novel series of benzimidazole-2-carboxamide derivatives was prepared and identified as NR2B selective NMDA receptor antagonists. The influence of some structural elements, like H-bond donor groups placed on the benzimidazole skeleton and the substitution pattern of the piperidine ring, on the biological activity was studied. Compound 6a showed excellent analgetic activity in the mouse formalin test following po administration. (c) 2006 Elsevier Ltd. All rights reserved.