1-benzyl-2-phenethyl-1H-benzo[d]imidazole | 882350-54-1

• 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-benzyl-2-phenethyl-1H-benzo[d]imidazole
• 英文别名: 1-Benzyl-2-(2-phenylethyl)benzimidazole
• CAS: 882350-54-1
• 化学式: C₂₂H₂₀N₂
• 分子量: 312.414
• InChiKey: XIPFARJLQCFGQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  苯乙烯 、 1-benzyl-1H-benzo[d]imidazole 在 bis(1,5-cyclooctadiene)nickel (0) 、 N-(2-(3-mesityl-2,3-dihydro-1H-imidazol-1-yl)ethyl)-2-methylpropan-2-amine 、 三甲基铝 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以90%的产率得到1-benzyl-2-phenethyl-1H-benzo[d]imidazole
  参考文献：
  名称：

  双金属镍铝通过C ？催化苯乙烯加氢杂芳基化区域选择性转换的机理研究。H激活

  摘要：

  我们以前报道为苯乙烯与苯并咪唑基于C的双金属镍-铝催化hydroheteroarylation一个高效的协议 H键活化。现在，我们描述了该过程的机制，为在路易斯酸AlMe 3存在下观察到的区域选择性转换提供了理论依据。目前的机理研究为合理开发具有所需线性/支化选择性的催化剂提供了见识。

  DOI：

  10.1002/chem.201400303

文献信息

• Iron-catalysed alkylation of 2-methyl and 4-methyl azaarenes with alcohols <i>via</i> C–H bond activation
  作者：Lalit Mohan Kabadwal、Sourajit Bera、Debasis Banerjee

  DOI：10.1039/d0cc01593h

  日期：——

  The first Fe-catalysed alkylation of 2-methyl and 4-methyl-azaarenes with a series of alkyl and hetero-aryl alcohols is reported (>39 examples and up to 95% yield). Multi-functionalisation of pyrazines and synthesis of anti-malarial drug (±) Angustureine significantly broaden the scope of this methodology. Preliminary mechanistic investigation, deuterium labeling and kinetic experiments including trapping

  报道了用一系列烷基和杂芳基醇进行的第一个Fe催化的2-甲基和4-甲基氮杂氮杂芳烃的烷基化反应（> 39个实例，收率高达95％）。吡嗪的多功能化和抗疟药（±）安格西汀的合成大大拓宽了该方法的范围。初步的机理研究，氘标记和动力学实验（包括捕集烯胺中间体1a'）特别重要。
• Cobalt-catalyzed alkylation of methyl-substituted N-heteroarenes with primary alcohols: direct access to functionalized N-heteroaromatics
  作者：Anju Mishra、Ambikesh D. Dwivedi、Sujan Shee、Sabuj Kundu

  DOI：10.1039/c9cc08448g

  日期：——

  Phosphine free, air and moisture stable Co(NNN) complex catalyzed alkylation of various methyl-substituted N-heteroarenes with alcohols is reported. Following the borrowing hydrogen methodology, a variety of methyl-substituted N-heteroarenes can be functionalized efficiently. To understand the mechanism of this reaction various kinetic and control experiments were carried out.

  据报道，无磷，空气和水分稳定的Co（NNN）络合物催化了各种甲基取代的N-杂芳烃与醇的烷基化反应。遵循借用氢方法，可以有效地官能化各种甲基取代的N-杂芳烃。为了理解该反应的机理，进行了各种动力学和控制实验。
• Manganese catalyzed C-alkylation of methyl <i>N</i>-heteroarenes with primary alcohols
  作者：Akash Jana、Amol Kumar、Biplab Maji

  DOI：10.1039/d1cc00181g

  日期：——

  C-Alkylations of nine different classes of methyl-substituted N-heteroarenes, including quinolines, quinoxalines, benzimidazoles, benzoxazoles, pyrazines, pyrimidines, pyridazines, pyridines, and triazines are disclosed. A bench stable earth-abundant Mn(I)-complex catalyzed the chemoselective hydrogen-transfer reaction utilizing a diverse range of primary alcohols as the non-fossil fuel-derived carbon

  公开了九种不同类别的甲基取代的N-杂芳烃的C-烷基化，包括喹啉，喹喔啉，苯并咪唑，苯并恶唑，吡嗪，嘧啶，哒嗪，吡啶和三嗪。台式稳定的富含地球的Mn（I）络合物利用多种伯醇作为非化石燃料衍生的碳源，催化化学选择性氢转移反应。以高收率和选择性分离出多样化的N-杂芳烃（41个实例）。水是唯一的副产物，使该方案对环境无害。
• Mechanistic Study of a Switch in the Regioselectivity of Hydroheteroarylation of Styrene Catalyzed by Bimetallic Ni-Al through CH Activation
  作者：Wen-Ching Chen、Ying-Chieh Lai、Wei-Chun Shih、Ming-Shiuan Yu、Glenn P. A. Yap、Tiow-Gan Ong

  DOI：10.1002/chem.201400303

  日期：2014.6.23

  previously reported a highly efficient protocol for bimetallic Ni–Al‐catalyzed hydroheteroarylation of styrene with benzimidazole based on CH bond activation. We have now delineated the mechanism of this process, providing a rationale for an observed switch in regioselectivity in the presence of the Lewis acid, AlMe3. The present mechanistic study gives insights for the rational development of catalysts

  我们以前报道为苯乙烯与苯并咪唑基于C的双金属镍-铝催化hydroheteroarylation一个高效的协议 H键活化。现在，我们描述了该过程的机制，为在路易斯酸AlMe 3存在下观察到的区域选择性转换提供了理论依据。目前的机理研究为合理开发具有所需线性/支化选择性的催化剂提供了见识。
• The Regioselective Switch for Amino-NHC Mediated C–H Activation of Benzimidazole via Ni–Al Synergistic Catalysis
  作者：Wei-Chun Shih、Wen-Ching Chen、Ying-Chieh Lai、Ming-Shiuan Yu、Jhao-Jhe Ho、Glenn P. A. Yap、Tiow-Gan Ong

  DOI：10.1021/ol300570f

  日期：2012.4.20

  We have disclosed a new mode of a chemically regioselective switch for C-H bond functionalization of benzimidazole derivatives via a cooperative effect invoked by Ni-Al bimetallic catalysis to create a steric requirement for obtaining the linear product of styrene insertion. Yet, excluding the AlMe3 cocatalyst switches the reaction toward branch selectivity.