3-benzyl-1-(N-phenylcarbamoylmethyl)imidazolium chloride | 935544-85-7

• 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: 3-benzyl-1-(N-phenylcarbamoylmethyl)imidazolium chloride
• CAS: 935544-85-7
• 化学式: C₁₈H₁₈N₃O*Cl
• 分子量: 327.813
• InChiKey: FSMPFSUFANTQFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.53
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  37.91
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-benzyl-1-(N-phenylcarbamoylmethyl)imidazolium chloride 在 K₂CO₃ 作用下， 以 吡啶 、 氯仿 为溶剂， 生成
  参考文献：
  名称：

  意外的溶剂诱导的顺式/反式异构化和具有N-杂环卡宾和酰胺基官能团的双齿双镍（II）配合物的催化应用

  摘要：

  由配体前体[L 1 H 1 H 2 ] Cl和[L 2 H 1 2 H 2 ] Cl（ H 1 = N H C O，H 2 = NC H N），产率为48-82％。NiL 1 2和Ni（L 2 H 1）2的络合物在空气和湿气中稳定。它们的特征在于NMR（1D和2D）和单晶X射线衍射研究。根据NMR，晶体学和PXRD研究，NiL 1 2络合物之一经历了一个有趣的可逆溶剂诱导的顺/反转化过程，用DMSO和CHCl 3产生了顺式。交换过程具有很高的特异性，可以用较高极性的cis-NiL 1 2来解释，这有利于极性DMSO溶剂，而由于配体的转位取消了极性而导致的极性较小的反式则有利于极性较小的CHCl 3溶剂。DFT计算支持实验结果。与先前报道的钯类似物不同，在PPh 3作为助催化剂的情况下，NiL 1 2和Ni（L 2 H 1）2在催化芳基氯化物与苯基硼酸的Suzuki交叉偶联反应中非常有效。3

  DOI：

  10.1021/om700607m
• 作为试剂：
  描述：

  3-氯苯腈 、 苯 在 3-benzyl-1-(N-phenylcarbamoylmethyl)imidazolium chloride 、 potassium tert-butylate 作用下， 反应 10.0h， 以50%的产率得到3-氰基联苯
  参考文献：
  名称：

  酰胺基官能化咪唑鎓盐催化的未活化芳烃的直接CH芳基化

  摘要：

  AbstractThe synthesis of biaryls from unactivated arenes and a broad range of aryl bromides and chlorides via the direct CH functionalization can be efficiently performed with the aid of amido‐functionalized imidazolium salts as organocatalysts. This method avoids the use of toxic transition metal catalysts and organometallic reagents.magnified image

  DOI：

  10.1002/adsc.201300877

文献信息

• Efficient Heck Reactions Catalyzed by Palladium(0) and -(II) Complexes Bearing N-Heterocyclic Carbene and Amide Functionalities
  作者：Jhen-Yi Lee、Pi-Yun Cheng、Yi-Hua Tsai、Guan-Ru Lin、Shih-Pu Liu、Ming-Han Sie、Hon Man Lee

  DOI：10.1021/om1006402

  日期：2010.9.13

  salt [LH1H2]Cl (H1 = NH proton; H2 NCHN proton). The X-ray diffraction studies confirmed that a η2-MA ligand and two monodentate NHC ligands with the H1 protons remaining intact are coordinated. These NH protons are involved in intra- or intermolecular hydrogen bonds stabilizing the solid-state structure. Degradation of Pd(LH1)2(MA) in air leads to the formation of the chelate complex trans-PdIIL2 and

  由酰胺-咪唑鎓盐[LH 1 H 2 ] Cl（H 1 = N H质子； H 2 NC H）制备钯（0）NHC复合物Pd 0（LH 1）2（MA）（MA =马来酸酐）N质子）。的X射线衍射研究证实，η 2 -MA配体和两个单齿NHC与H配体1个质子保持完整协调。这些NH质子参与稳定固态结构的分子内或分子间氢键。空气中Pd（LH 1）2（MA）的降解导致螯合物的形成反式-Pd II L 2和其他身份不明的产品。负离子电喷雾质谱法显示了一些有趣的Pd（0）物种，包括仅带有双齿NHC /酰胺基配体的14电子[Pd 0 L] -物种。X射线光电子研究表明，阴离子酰胺基团在钯中心上具有高电子密度。钯（0）预催化剂在催化离子液体中与活化的芳基氯化物的Heck反应方面非常有效。为了使芳基氯和笨重的芳基溴失活，顺式-Pd II L 2更有效。Pd 0（LH 1）2（MA）和顺式-Pd II L 2。后者配合
• A Heteroleptic Palladium(II) Complex Containing a Bidentate Carbene/Amido Ligand and 3-(Trifluoromethyl)-5-(2-pyridyl)pyrazolate: Fast Catalyst Activation in the Heck Coupling Reaction
  作者：Ming-Han Sie、Yuan-Hsin Hsieh、Yi-Hua Tsai、Jia-Rong Wu、Shih-Jung Chen、P. Vijaya Kumar、Jenn-Huei Lii、Hon Man Lee

  DOI：10.1021/om100819q

  日期：2010.12.13

  photoelectron spectroscopy indicates the high electron richness of the palladium atoms in PdL(fppz). These palladium complexes are efficient in catalyzing Heck coupling reactions with challenging aryl halide substrates. The catalyst activation in PdL(fppz) is significantly faster than that in cis-PdL2. A mere 0.5 mol % of palladium loading is enough to afford a 82% yield of coupled product from 4-chloroanisole

  在K 2 CO 3存在下PdCl 2，fppzH和[LH 1 H 2 ] Cl之间的多组分反应（L ＝双齿酰胺基/卡宾； fppzH ＝ 3-（三氟甲基）-5-（2-吡啶基）吡唑）可以制备高产率的PdL（fppz）。然而，类似的铂络合物需要通过两步程序来制备。通过1D和2D NMR光谱，X射线晶体学，电喷雾电离质谱和元素分析对新型钯（II）和铂（II）配合物进行了表征。X射线光电子能谱表明PdL（fppz）中钯原子的电子富集度很高。这些钯配合物可有效催化具有挑战性的芳基卤化物底物的Heck偶联反应。PdL（fppz）中的催化剂活化明显快于顺式-PdL 2中的催化剂活化。仅仅0.5mol％的钯负载量足以在24小时内从4-氯苯甲醚和苯乙烯获得82％的偶联产物收率。
• Nonchelate and Chelate Complexes of Palladium(II) with N-Heterocyclic Carbene Ligands of Amido Functionality
  作者：Chuang-Yi Liao、Kai-Ting Chan、Jing-Yao Zeng、Ching-Han Hu、Cheng-Yi Tu、Hon Man Lee

  DOI：10.1021/om0610041

  日期：2007.3.1

  The imidazolium ligand precursors [(LHH2)-H-1-H-1]Cl and [(LH2H2)-H-2-H-1]Cl (H-1 = NHCO, H-2 = NCHN) for the potentially bidentate and pincer-type amido-NHC ligands were synthesized in 66-78% yields. Selective deprotonation of H-2 in these salts with pyridine in the presence of palladium chloride resulted in the monodentate palladium(II) complexes Pd((LH1)-H-1)(py)Cl-2 and Pd((LH21)-H-2)(py)Cl-2. The use of K2CO3 in pyridine or DMF led to the double and triple deprotonations of the ligand precursors, giving the bis-bidentate and pincer-type palladium(II) complexes PdL21 and PdL2(py), respectively. Intriguingly, in certain cases, both the cis and the trans isomers of PdL21 were formed and isolated in pure forms. A theoretical study indicates that the trans-PdL21 is thermodynamically more stable than the cis isomer (ca. 5.8 kcal mol(-1)). All the new complexes are characterized by NMR (1D and 2D) and single-crystal X-ray diffraction studies. A systematic study of the new complexes in Suzuki coupling reactions revealed the following order of activities: Pd((LH1)-H-1)(py)Cl-2 > PdL2(py) > PdL21.
• Structural variation in silver complexes with N-heterocyclic carbene ligands bearing amido functionality
  作者：Chuang-Yi Liao、Kai-Ting Chan、Pei-Ling Chiu、Chih-Yuan Chen、Hon Man Lee

  DOI：10.1016/j.ica.2007.10.051

  日期：2008.6

  Silver complexes derived from reactions of silver(I) oxide and imidazolium precursors [(LHH2)-H-1-H-1]Cl and [(L2H2H2)-H-1]Cl in DMF were reported. The crystallographic analyses confirmed that all these silver complexes are 1:1 Ag/NHC complexes in the solid states with formulae of Ag((LH1)-H-1)Cl and Ag((LH21)-H-2)Cl, respectively. The amido proton (H-1) remains intact. Their solid-state structures markedly depend on their N-substitutions on the ligand frameworks. The C-Ag-Cl bond angles are ca. 150 degrees in Ag((LH1)-H-1)Cl complexes bearing N-benzyl groups, whereas the angle is linear in Ag((LH21)-H-2)Cl bearing two N-amido functional groups. The obtuse bond angles in Ag((LH1)-H-1)Cl permit the formation of infinite 1D staircase motifs via bridging Cl and hydrogen bonding interactions. No such motif exists in the structure with the linear bond angle. (c) 2007 Elsevier B. V. All rights reserved.