4,4,5,5-tetramethyl-1,3-diphenyl-4,5-dihydro-1H-imidazol-3-ium chloride | 1029877-11-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,4,5,5-tetramethyl-1,3-diphenyl-4,5-dihydro-1H-imidazol-3-ium chloride
• 英文别名: 1,3-diphenyI-4,4,5,5-tetramethyl-imidazol-2-ium chloride；4,4,5,5-Tetramethyl-1,3-diphenylimidazol-1-ium;chloride
• CAS: 1029877-11-9
• 化学式: C₁₉H₂₃N₂*Cl
• 分子量: 314.858
• InChiKey: TWYNTDJTMDTRAA-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.44
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  6.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4,4,5,5-tetramethyl-1,3-diphenyl-4,5-dihydro-1H-imidazol-3-ium chloride 在 双(三甲基硅烷基)氨基钾 作用下， 以 苯 为溶剂， 反应 0.25h， 生成 4,4,5,5-tetramethyl-1,3-diphenyl-2H-imidazol-1-ium-2-ide
  参考文献：
  名称：

  Olefin Metathesis Catalyst: Stabilization Effect of Backbone Substitutions of N-Heterocyclic Carbene

  摘要：

  Ruthenium olefin metathesis catalysts bearing an N-phenyl-substituted N-heterocyclic carbene (NHC) ligand that are resistant to decomposition through C-H activation have been prepared and tested in ring closing metathesis (RCM), cross metathesis (CM), and ROMP reactions. The N,N '-diphenyl-substituted NHC complex proved to be one of the most efficient catalysts in RCM to form tetrasubstituted olefins.

  DOI：

  10.1021/ol800824h
• 作为产物：
  描述：

  1,1,2,2-tetramethyl-N,N'-diphenyl-ethanediyldiamine 、 原甲酸三乙酯 在 盐酸 作用下， 以 1,4-二氧六环 、 乙醚 为溶剂， 反应 0.17h， 以79%的产率得到4,4,5,5-tetramethyl-1,3-diphenyl-4,5-dihydro-1H-imidazol-3-ium chloride
  参考文献：
  名称：

  Olefin Metathesis Catalyst: Stabilization Effect of Backbone Substitutions of N-Heterocyclic Carbene

  摘要：

  Ruthenium olefin metathesis catalysts bearing an N-phenyl-substituted N-heterocyclic carbene (NHC) ligand that are resistant to decomposition through C-H activation have been prepared and tested in ring closing metathesis (RCM), cross metathesis (CM), and ROMP reactions. The N,N '-diphenyl-substituted NHC complex proved to be one of the most efficient catalysts in RCM to form tetrasubstituted olefins.

  DOI：

  10.1021/ol800824h

文献信息

• [EN] RUTHENIUM OLEFIN METATHESIS CATALYSTS BEARING N-HETEROCYCLIC CARBENE LIGANDS WITH SUBSTITUTED BACKBONE<br/>[FR] CATALYSEURS DE MÉTATHÈSE D'OLÉFINES À BASE DE RUTHÉNIUM PORTANT DES LIGANDS CARBÈNES N-HÉTÉROCYCLIQUES À SQUELETTE SUBSTITUÉ
  申请人：MATERIA INC

  公开号：WO2009126831A1

  公开（公告）日：2009-10-15

  This invention relates generally to olefin metathesis, more particularly, to tri- or tetra-substituted imidazoliniυm salts which are precursors to N-heterocyclic carbene (NHC) ligands with tri- or tetra-substituted irnidazolinium rings, organometallic ruthenium complexes comprising gem di-substituted imidazoiinium NHC ligands, organometallic ruthenium complexes comprising tri- or tetra-substituted imidazoiinium NHC ligands, and to olefin metathesis methods using them. The catalysts and methods of the invention have utility in the fields of catalysis, organic synthesis, and industrial chemistry.

  本发明通常涉及烯烃转化反应，更具体地涉及三取代或四取代咪唑啉盐，这些盐是N-杂环卡宾（NHC）配体的前体，具有三取代或四取代咪唑啉环的有机金属钌配合物，包含宝石二取代咪唑啉NHC配体的有机金属钌配合物，包含三取代或四取代咪唑啉NHC配体的有机金属钌配合物，以及使用它们的烯烃转化反应方法。本发明的催化剂和方法在催化、有机合成和工业化学领域具有实用性。
• RUTHENIUM OLEFIN METATHESIS CATALYSTS BEARING N-HETEROCYCLIC CARBENE LIGANDS WITH SUBSTITUTED BACKBONE
  申请人：Grubbs Robert H.

  公开号：US20110124868A1

  公开（公告）日：2011-05-26

  This invention relates generally to olefin metathesis, more particularly, to tri- or tetra-substituted imidazolinium salts which are precursors to N-heterocyclic carbene (NHC) ligands with tri- or tetra-substituted imidazolinium rings, organometallic ruthenium complexes comprising gem di-substituted imidazolinium NHC ligands, organometallic ruthenium complexes comprising tri- or tetra-substituted imidazolinium NHC ligands, and to olefin metathesis methods using them. The catalysts and methods of the invention have utility in the fields of catalysis, organic synthesis, and industrial chemistry.

  本发明涉及烯烃交换反应，更具体地涉及三或四取代咪唑啉盐，其是三或四取代咪唑啉环的N-杂环卡宾（NHC）配体的前体，包括含有宝石二取代咪唑啉NHC配体的有机金属钌配合物，含有三或四取代咪唑啉NHC配体的有机金属钌配合物，以及使用它们的烯烃交换反应方法。该发明的催化剂和方法在催化、有机合成和工业化学领域具有实用性。
• Pursuing <i>E</i>-Selective Olefin Metathesis: Tuning Steric and Electronic Properties of S,N-Chelated Ruthenium Alkylidenes
  作者：Immanuel Reim、Giovanni Occhipinti、Karl W. Törnroos、Vidar R. Jensen

  DOI：10.1021/acs.organomet.3c00522

  日期：2024.4.8

  investigated N-heterocyclic carbene (NHC) ligands that are less bulky than Me2IMes. We also hypothesized that a S,N ligand with a less nucleophilic nitrogen atom than that of indole might improve catalyst stability. However, catalyst Ru7, bearing 2-sulfidophenyltrifluoromethylsulfonylamide L2 instead of L1, was not significantly more productive or E-selective than Ru5. Whereas Ru nanoparticles formed on

  在第一个Z-选择性复分解催化剂被报道十多年后，直接从1-烯烃选择性形成E-烯烃仍然是一个未解决的问题。硫代吲哚内酯基复合物Ru5 (Ru( L1 )( Me 2 IMes )(py)(=CHR); Me 2 IMes = 1,3-二甲基-4,5-二甲基咪唑-2-亚基; py =吡啶；R = 2-噻吩基；L1 = 7-硫代吲哚-1-化物）最初通过密度泛函理论（DFT）计算预测为E选择性。然而，Ru5被证明具有较低的催化活性，并且由于异常受阻的产物解离而具有中等的Z选择性 [Reim 等人，2017]。顶部。加塔尔。 2022, 65, 448]。为了降低解离势垒，我们在这里研究了比Me 2 IMes体积更小的 N-杂环卡宾 (NHC) 配体。我们还假设具有比吲哚更少亲核氮原子的 S,N 配体可能会提高催化剂稳定性。然而，带有2-硫基苯基三氟甲基磺酰胺L2而不是L1的催化剂Ru7并不比Ru5显着更高的产率或E选择性。虽然
• US8877936B2
  申请人：——

  公开号：US8877936B2

  公开（公告）日：2014-11-04