1-isopropyl-3-methyl-2,4-diphenylimidazolium iodide | 700816-99-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-isopropyl-3-methyl-2,4-diphenylimidazolium iodide
• 英文别名: 3-Methyl-2,4-diphenyl-1-propan-2-ylimidazol-1-ium;iodide
• CAS: 700816-99-5
• 化学式: C₁₉H₂₁N₂*I
• 分子量: 404.294
• InChiKey: PROVAPBJVSDFSD-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.23
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  8.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-isopropyl-3-methyl-2,4-diphenylimidazolium iodide 、 palladium diacetate 以 1,4-二氧六环 为溶剂， 以46.9%的产率得到
  参考文献：
  名称：

  Abnormal N-Heterocyclic Carbene Promoted Suzuki−Miyaura Coupling Reaction: A Comparative Study

  摘要：

  A C2-protected imidazolium salt that generates an abnormal N-heterocyclic carbene (NHC) was applied for the palladium-catalyzed Suzuki-Miyaura coupling reactions. The abnormal NHC precursor promoted the reactions while suppressing homocoupling of aryl boronic acid, which was observed with the corresponding normal NHC precursor. The related well-defined abnormal NHC-based palladium complexes also showed better activity than the normal NHC-based analogues, exhibiting faster reaction rates especially at the initial stage of the reaction.

  DOI：

  10.1021/om100746r
• 作为试剂：
  描述：

  2,6-二甲氧基苯硼酸 、 4-溴苯乙酮 在 1-isopropyl-3-methyl-2,4-diphenylimidazolium iodide 、 palladium diacetate 、 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以55%的产率得到2,6-dimethoxy-4'-acetylbiphenyl
  参考文献：
  名称：

  Abnormal N-Heterocyclic Carbene Promoted Suzuki−Miyaura Coupling Reaction: A Comparative Study

  摘要：

  A C2-protected imidazolium salt that generates an abnormal N-heterocyclic carbene (NHC) was applied for the palladium-catalyzed Suzuki-Miyaura coupling reactions. The abnormal NHC precursor promoted the reactions while suppressing homocoupling of aryl boronic acid, which was observed with the corresponding normal NHC precursor. The related well-defined abnormal NHC-based palladium complexes also showed better activity than the normal NHC-based analogues, exhibiting faster reaction rates especially at the initial stage of the reaction.

  DOI：

  10.1021/om100746r

文献信息

• Abnormal N-Heterocyclic Carbene Gold(I) Complexes: Synthesis, Structure, and Catalysis in Hydration of Alkynes
  作者：Xiangya Xu、Seung Hyo Kim、Xi Zhang、Atanu Kumar Das、Hajime Hirao、Soon Hyeok Hong

  DOI：10.1021/om3009603

  日期：2013.1.14

  sterically similar NHC-based Au complexes chloro(1,3-diisopropylimidazol-2-ylidene)gold(I) (7) and chloro(3-isopropyl-1-phenylimidazol-2-ylidene)gold(I) (8) were prepared from 1,3-diisopropylimidazolium iodide (3) and 3-isopropyl-1-phenylimidazolium iodide (4), respectively. X-ray crystallography and density functional theory (DFT) calculations showed that the aNHC complexes have longer Au–Ccarbene bond

  从C2保护的咪唑鎓盐制备了两种异常的N-杂环卡宾（aNHC）金（I）络合物[（aNHC）AuCl]。空气稳定的络合物氯（1-异丙基-3-甲基-2,4-二苯基咪唑-5-亚甲基）金（I）（5）和氯（1,4-二异丙基-3-甲基-2-甲基-2-苯基咪唑-5 -亚基）金（I）（6）用（SME通过转移金属化合成2）AUCL和相应的银盐如[（aNHC）的AgI]或[（aNHC）2Ag] [I]并通过NMR和质谱以及X射线晶体学进行了全面表征。为了研究基于aNHC的Au络合物与其传统的NHC类似物的结构，键合和催化活性，在空间上相似的基于NHC的Au络合物氯（1,3-二异丙基咪唑-2-亚烷基）金（I）（7）和氯（3-异丙基-1-苯基咪唑-2-亚甲基）金（I）（8）分别由1,3-二异丙基碘咪唑鎓碘化物（3）和3-异丙基-1-苯基咪唑碘化物碘化物（4）制备。 。X射线晶体学和密度泛函理论（DFT）计算表明，a
• Abnormal C5-Bound N-Heterocyclic Carbenes:  Extremely Strong Electron Donor Ligands and Their Iridium(I) and Iridium(III) Complexes
  作者：Anthony R. Chianese、Anes Kovacevic、Brian M. Zeglis、J. W. Faller、Robert H. Crabtree

  DOI：10.1021/om049903h

  日期：2004.5.1

  Imidazolium salts are found to bind abnormally via C5 to iridium(I) and iridium(III) to give air-stable monodentate N-heterocyclic carbene complexes. Abnormal ligand binding was verified by X-ray diffraction in both Ir(I) and Ir(III) complexes. In the case of Ir(I), it is necessary to block the C2 and C4 positions to form a stable sterically protected C5-bound complex. Infrared spectroscopy on carbonyl

  发现咪唑鎓盐通过C5与铱（I）和铱（III）异常结合，生成空气稳定的单齿N-杂环卡宾配合物。通过X射线衍射在Ir（I）和Ir（III）络合物中验证了异常的配体结合。在Ir（I）的情况下，有必要封闭C2和C4的位置以形成稳定的，受空间保护的C5结合的复合物。羰基衍生物的红外光谱表明，异常结合的N-杂环卡宾比其普遍存在的C2结合的对应物更强大的电子供体。相对于ca的1-异丙基-2,4-二苯基-3-甲基咪唑啉-5-亚烷基的Tolman电子参数为2039 cm - 1。2050厘米- 1为典型的NHC。