5-methoxy-2-methyl-1-phenyl-1H-benzo[d]imidazole | 444995-63-5

• 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: 5-methoxy-2-methyl-1-phenyl-1H-benzo[d]imidazole
• 英文别名: 5-methoxy-2-methyl-1-phenyl-1H-benzoimidazole；5-methoxy-2-methyl-1-phenylbenzimidazole；5-methoxy-2-methyl-1-phenyl-1H-benzimidazole；5-Methoxy-2-methyl-1-phenyl-1H-benzimidazol；5-Methoxy-2-methyl-1-phenyl-1H-benzimidazole
• CAS: 444995-63-5
• 化学式: C₁₅H₁₄N₂O
• 分子量: 238.289
• InChiKey: FBNNOTJDULWWCJ-UHFFFAOYSA-N

物化性质

• 熔点：
  103-105 °C
• 沸点：
  416.4±37.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-(4-methoxy-2-nitrophenyl)-N-phenylacetamide 在 铁粉 、 溶剂黄146 作用下， 反应 0.5h， 生成 5-methoxy-2-methyl-1-phenyl-1H-benzo[d]imidazole
  参考文献：
  名称：

  N-取代苯并咪唑和咪唑并吡啶的直接、区域选择性钯催化合成

  摘要：

  不对称的、N-取代的苯并咪唑和咪唑并吡啶可以直接从 2-卤代硝基芳烃和酰胺通过 Pd(TFA) 2 /(R)-BINAP 催化的交叉偶联和随后的还原性氨基环化来制备。该序列可以通过一锅法进行。该方法用途广泛，可以直接、区域选择性地制备这些重要的氮杂环。

  DOI：

  10.1002/ejoc.201001423
• 作为试剂：
  描述：

  4-碘基-3-硝基苯甲醚 、 N-乙酰苯胺 在 5-methoxy-2-methyl-1-phenyl-1H-benzo[d]imidazole 作用下， 以to yield the title compound as a pale yellow solid (80 mg, 67%)的产率得到5-methoxy-2-methyl-1-phenyl-1H-benzo[d]imidazole
  参考文献：
  名称：

  Regioselective copper catalyzed synthesis of benzimidazoles and azabenzimidazoles

  摘要：

  本发明涉及一种用于合成式I化合物的区域选择性合成方法，其中R0；R1；R2；R3；R4；R5；A1；A2；A3；A4，Q和J具有所述声明中指定的含义。本发明提供了一种直接铜催化的区域选择性过程，从2-卤代硝基芳烃和N-取代酰胺开始，可合成一种广泛的非对称、多功能N-取代苯并咪唑或氮杂苯并咪唑式I化合物。

  公开号：

  US08735586B2

文献信息

• Iridium-catalyzed intramolecular C N and C O/S cross-coupling reactions: Preparation of benzoazole derivatives
  作者：Yajie Shi、Qifan Zhou、Fangyu Du、Yang Fu、Yang Du、Ting Fang、Guoliang Chen

  DOI：10.1016/j.tetlet.2019.151082

  日期：2019.10

  The irdium-catalyzed intramolecular arylcarbon-hetero cross-coupling reactions with o-haloarylamides or o-haloarylamidine have been effectively achieved using KOAc and just 1 mol% catalyst. The [Ir(cod)Cl]2 was proved to be more potential for smoothly assembling functional structures benzimidazoles, benzoxazoles and benzothiazoles, which was superior to Cu- and Pd-catalyzed systems. Simultaneously

  使用KOAc和仅1mol％的催化剂已经有效地实现了铱催化的与邻卤代芳基酰胺或邻卤代芳基idine杂的分子内芳基碳杂交联反应。事实证明，[Ir（cod）Cl] 2具有更大的潜力，可以平稳地组装功能结构苯并咪唑，苯并恶唑和苯并噻唑，优于铜和钯催化的体系。同时，开发了一种5 g规模的简洁而有效的tafamidis合成方法。
• An Improved Procedure for the Synthesis of Benzimidazoles, Using Palladium-Catalyzed Aryl-Amination Chemistry
  作者：Christopher T. Brain、James T. Steer

  DOI：10.1021/jo034824l

  日期：2003.8.1

  New, improved conditions have been developed and optimized for the synthesis of benzimidazoles by intramolecular palladium-catalyzed aryl-amination chemistry. This methodology, combined with a "catch and release" purification strategy, has led to a range of these heterocycles being prepared rapidly and in excellent yield.

  为通过分子内钯催化的芳基胺化化学合成苯并咪唑开发了新的，改进的条件，并对其进行了优化。这种方法与“捕获和释放”纯化策略相结合，已导致快速制备了一系列这些杂环，并具有优异的收率。
• A regioselective palladium catalyzed synthesis of benzimidazoles and azabenzimidazoles
  申请人：sanofi-aventis

  公开号：EP1878724A1

  公开（公告）日：2008-01-16

  The present invention relates to a process for the regioselective synthesis of compounds of the formula I, wherein R0; R1; R2; R3; R4; R5; A1; A2; A3; A4, Q and J have the meanings indicated in the claims. The present invention provides a direct palladium catalyzed, regioselective process to a wide variety of unsymmetrical, multifunctional N-substituted benzimidazoles or azabenzimidazoles of formula I starting from 2-halo-nitroarenes and N-substituted amides useful for the production of pharmaceuticals, diagnostic agents, liquid crystals, polymers, herbicides, fungicidals, nematicidals, parasiticides, insecticides, acaricitdes and arthropodicides.

  本发明涉及一种用于合成式I化合物的区域选择性合成过程，其中R0；R1；R2；R3；R4；R5；A1；A2；A3；A4，Q和J的含义如权利要求中所示。本发明提供了一种直接钯催化的、区域选择性的过程，可从2-卤代硝基芳烃和N-取代酰胺出发，合成多种非对称的、多功能的N-取代苯并咪唑或氮代苯并咪唑的式I化合物，用于生产药物、诊断试剂、液晶、聚合物、除草剂、杀菌剂、线虫杀灭剂、杀虫剂、螨虫剂和节肢动物杀虫剂。
• Regioselective palladium catalyzed synthesis of benzimidazoles and azabenzimidazoles
  申请人：Sanofi-Aventis

  公开号：US08188282B2

  公开（公告）日：2012-05-29

  The present invention relates to a process for the regioselective synthesis of compounds of the formula I, wherein R0; R1; R2; R3; R4; R5; A1; A2; A3; A4, Q and J have the meanings indicated in the claims. The present invention provides a direct palladium catalyzed, regioselective process to a wide variety of unsymmetrical, multifunctional N-substituted benzimidazoles or azabenzimidazoles of formula I starting from 2-halo-nitroarenes and N-substituted amides useful for the production of pharmaceuticals, diagnostic agents, liquid crystals, polymers, herbicides, fungicidals, nematicidals, parasiticides, insecticides, acaricides and arthropodicides.

  本发明涉及一种合成式I化合物的区域选择性合成过程，其中R0; R1; R2; R3; R4; R5; A1; A2; A3; A4，Q和J具有所述权利要求中指示的含义。本发明提供了一种直接钯催化的、区域选择性的过程，可以从2-卤代硝基芳烃和N-取代酰胺开始，合成多种非对称、多功能的N-取代苯并咪唑或氮杂苯并咪唑式I化合物，这些化合物可用于制药、诊断试剂、液晶、聚合物、除草剂、杀菌剂、线虫杀剂、驱虫剂、杀虫剂、杀螨剂和杀节肢动物剂的生产。
• An intramolecular palladium-catalysed aryl amination reaction to produce benzimidazoles
  作者：Christopher T Brain、Shirley A Brunton

  DOI：10.1016/s0040-4039(02)00132-6

  日期：2002.3

  A novel synthesis of benzimidazoles by a palladium-catalysed intramolecular N-arylation reaction from (o-bromophenyl)amidine precursors is described. (C) 2002 Elsevier Science Ltd. All rights reserved.