N¹-benzyl-4-methylbenzimidazole | 73902-59-7

• 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: N¹-benzyl-4-methylbenzimidazole
• 英文别名: 1-benzyl-4-methylbenzimidazole；N-benzyl-4-methylbenzimidazole；1-Benzyl-4-methylbenzimidazol；1-benzyl-4-methyl-1H-benzoimidazole；1-Benzyl-4-methyl-1H-benzimidazole
• CAS: 73902-59-7
• 化学式: C₁₅H₁₄N₂
• 分子量: 222.29
• InChiKey: JVOMREBFYWKLLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N¹-benzyl-4-methylbenzimidazole 在 三乙基硅烷 、 palladium 10% on activated carbon 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以6%的产率得到7 - 甲基-1H -苯并[D]咪唑
  参考文献：
  名称：

  用三乙基硅烷和Pd / C对N-苄基苯并咪唑和N-苄基咪唑进行脱保护

  摘要：

  苄基是苯并咪唑和咪唑的保护基，可以在酸性，碱性，氧化和还原条件下存活。然而，脱保护可能需要有力的并且可能是非化学选择性的方法。三乙基硅烷-Pd / C还原系统是一种非常温和，方便，有效的方法，用于保护在2位和4位未被取代的N-苄基苯并咪唑以及适当取代的N-苄基咪唑。

  DOI：

  10.1016/j.tetlet.2015.03.127
• 作为产物：
  描述：

  7 - 甲基-1H -苯并[D]咪唑 生成 N¹-benzyl-4-methylbenzimidazole
  参考文献：
  名称：

  Haque M. Rezaul, Rasmussen Malcolm, Tetrahedron, 50 (1994) N 18, S 5535-5554

  摘要：

  DOI：

文献信息

• Michael Adducts in the Regioselective Synthesis of N-Substituted Azoles
  作者：András Horváth

  DOI：10.1055/s-1995-4054

  日期：1995.9

  Michael adducts of azoles (4-phenyl-, 4-methyl- and 4-nitroimidazole, 4-methylbenzimidazole, 1,2,4-triazole and theophylline) are shown to be valuable substrates for obtaining the N-substituted derivatives of the parent heterocycles by a quaternization-Hofmann elimination sequence. The effectiveness of the procedure is dependent on the regiochemical outcome of the first, N-protective step, i.e. the Michael addition. By choosing the appropriate Michael acceptor, alkylating agent and deprotection conditions, the thermodynamically less stable regioisomers of N-substituted azoles have been obtained in high yields.

  米哈伊尔加成物的偶氮物（4-苯基、4-甲基和4-硝基咪唑、4-甲基苯并咪唑、1,2,4-三唑和茶碱）被证明是获得母体杂环的N-取代衍生物的重要底物，这一过程通过一个季铵化-霍夫曼消除序列实现。该程序的有效性取决于第一个N保护步骤（即迈克尔加成）的区域化学结果。通过选择适当的迈克尔受体、烷基化试剂和去保护条件，可以以高产率获得N-取代偶氮物的热力学不太稳定的区域异构体。
• Ambident heterocyclic reactivity: Alkylation of 2-substituted-4-methylbenzimidazoles
  作者：M.Rezaul Haque、Malcolm Rasmussen

  DOI：10.1016/s0040-4020(01)80708-0

  日期：1994.5

  inducing changes in alkylation regioselectivity. The combined results are consistent with dominant ‘steric approach control’ for the alkylations, where the magnitude of the steric effect is critically dependent on the length of the developing N - - - C bond in the variable geometry SN2 alkylation transition states involved. Unequal steric effects of 2-substituents on N1 and N3 alkylations and their variation

  确定了对4-甲基-，2,4-二甲基-，2-氨基-4-甲基-，2-氯-4-甲基-，2-乙氧基-4-甲基-苯并咪唑和4-甲基的烷基化的区域选择性。甲基苯并咪唑酮（作为二甲基甲酰胺中的阴离子）与各种伯烷基化剂。在可比较的条件下，这些N 1 / N 3区域选择性与这些热杂环阴离子的苄基化的二级速率常数（苄基氯/二甲基甲酰胺/ 30°）相关。改变所述烷基化剂，[R “CH 2氯，导致沿S的松密轴移动Ñ 2过渡态的结构，并产生在区域选择性显着变化。沿晚期S N的变化由改变2- R -4-甲基苯并咪唑阴离子中的2-取代基引起的2轴在诱导烷基化区域选择性变化方面效果不佳。结合的结果与烷基化的主要“空间方法控制”相一致，其中空间效应的大小主要取决于所涉及的可变几何结构S N 2烷基化过渡态中正在发展的N--C键的长度。2-取代基对N 1和N 3烷基化的不等空间效应及其随烷基化剂的变化是通过调用氮烷基化位点的
• LIGAND EXCHANGE THERMOCHROMIC SYSTEMS AND HIGH E LIGANDS FOR SAME
  申请人：Byker J. Harlan

  公开号：US20080105851A1

  公开（公告）日：2008-05-08

  Ligand exchange of thermochromic, LETC, systems exhibiting a reversible change in absorbance of electromagnetic radiation as the temperature of the system is reversibly changed are described. The described LETC systems include one or more than one transition metal ion, which experiences thermally induced changes in the nature of the complexation or coordination around the transition metal ion(s) and, thereby, the system changes its ability to absorb electromagnetic radiation as the temperature changes. In accordance with certain aspects of the present invention, a thermochromic system is disclosed comprising a transition metal ion and a ligand wherein the ligand comprises a nitrogen-containing five or six membered heterocyclic compound that coordinates through the nitrogen atom to the transition metal ion in a HεMLC formed between the transition metal ion and the ligand. In accordance with other aspects of the present invention, thermochromic systems are disclosed comprising a transition metal ion with particularly useful ligands, such as phosphine compounds, tridentate ligands that coordinate through three nitrogen atoms, bidentate ligands, or ortho hindered pyridine monodentate ligands.

  本文描述了具有热致变色性质的配体交换（LETC）系统，当系统的温度可逆变化时，电磁辐射吸收率也可逆变化。所述的LETC系统包括一个或多个过渡金属离子，其经历热诱导的配位或配位环境的变化，从而使系统随着温度变化而改变吸收电磁辐射的能力。根据本发明的某些方面，公开了包括过渡金属离子和配体的热致变色系统，其中配体包括通过氮原子与过渡金属离子形成的HεMLC（配体与过渡金属离子之间的配位键）的含氮五元或六元杂环化合物。根据本发明的其他方面，公开了包括具有特别有用的配体的过渡金属离子的热致变色系统，例如膦化合物、通过三个氮原子配位的三齿配体、双齿配体或邻位受阻的吡啶单齿配体。
• LIGAND EXCHANGE THERMOCHROMIC SYSTEMS CONTAINING EXCHANGE METALS
  申请人：Byker J. Harlan

  公开号：US20080106781A1

  公开（公告）日：2008-05-08

  Ligand exchange of thermochromic, LETC, systems exhibiting a reversible change in absorbance of electromagnetic radiation as the temperature of the system is reversibly changed are described. The described LETC systems include one or more than one transition metal ion, which experiences thermally induced changes in the nature of the complexation or coordination around the transition metal ion(s) and, thereby, the system changes its ability to absorb electromagnetic radiation as the temperature changes. In accordance with one aspect of the present invention, a thermochromic system is disclosed comprising a first metal ion and a second metal ion and at least one ligand that complexes with the first metal ion to form a LεMLC and complexes with the second metal ion to form a HεMLC wherein an increase in temperature of the system results in a reversible net increase in its ability to absorb light energy in the 400 nm to 1400 nm range due to the ligand transferring from the first metal ion to the second metal ion.

  本文介绍了一种具有热致变色特性的配体交换系统，当系统的温度可逆变化时，其吸收电磁辐射的能力也可逆变化。所述的LETC系统包括一个或多个过渡金属离子，其在过渡金属离子周围的络合或配位发生热诱导变化，从而使系统随着温度变化而改变吸收电磁辐射的能力。根据本发明的一个方面，公开了一种热致变色系统，包括第一金属离子和第二金属离子以及至少一个配体，该配体与第一金属离子形成LεMLC配合物，并与第二金属离子形成HεMLC配合物，系统温度的升高导致可逆的净吸收光能力增加，范围为400纳米至1400纳米，这是由于配体从第一金属离子转移到第二金属离子造成的。
• LIGAND EXCHANGE THERMOCHROMIC, (LETC), SYSTEMS
  申请人：Byker J. Harlan

  公开号：US20080100902A1

  公开（公告）日：2008-05-01

  Ligand exchange of thermochromic, LETC, systems exhibiting a reversible change in absorbance of electromagnetic radiation as the temperature of the system is reversibly changed are described. The described LETC systems include one or more than one transition metal ion, which experiences thermally induced changes in the nature of the complexation or coordination around the transition metal ion(s) and, thereby, the system changes its ability to absorb electromagnetic radiation as the temperature changes.

  本文介绍了一种热致变色（LETC）系统的配体交换方法，该系统在温度可逆变化时显示出电磁辐射吸收的可逆变化。所述LETC系统包括一个或多个过渡金属离子，其在过渡金属离子周围的配位或络合性质发生热诱导变化，从而使系统在温度变化时改变吸收电磁辐射的能力。