1-(2,4,6-trimethylbenzyl)imidazoline | 587887-00-1

• 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: 1-(2,4,6-trimethylbenzyl)imidazoline
• 英文别名: 1-[(2,4,6-trimethylphenyl)methyl]-4,5-dihydroimidazole
• CAS: 587887-00-1
• 化学式: C₁₃H₁₈N₂
• 分子量: 202.299
• InChiKey: DOPWOHIJZKBZBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  15.6
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(2,4,6-trimethylbenzyl)imidazoline 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 bis[1-(2,4,6-trimethylbenzyl)-3-(4-chlorobenzyl)imidazolidin-2-ylidene]dichloropalladium(II)
  参考文献：
  名称：

  Arylation of Aniline and Amines by Pd-(N-Heterocyclic Carbene) Complexes

  摘要：

  Aminoarenes constitute valuable building blocks in organic synthesis and an essential skeleton ubiquitously found in ligands, agrochemicals, and pharmaceuticals. This synopsis presents recent amination methods using nitrogen-heteroatom bonds as a powerful and versatile platform to rapidly synthesize diverse aminoarenes, with transition-metal catalyzed arene C-H amination. The Buchwald-Hartwig amination has been investigated theoretically and experimentally to examine the scope of possible bases under different reaction conditions. We report examples of the palladium NHC (N-heterocyclic carbene) catalyzed amination of aryl halides with anilines and amines in the presence of dimethoxyethane solvent and potassium tertiary-butoxide as a base.

  DOI：

  10.3987/com-17-13737
• 作为产物：
  描述：

  2,4,6-三甲基氯苄 在 lithium 作用下， 反应 3.0h， 生成 1-(2,4,6-trimethylbenzyl)imidazoline
  参考文献：
  名称：

  A theoretical insight for solvent effect on myoglobin assay of W(CO)4L2 type novel complexes with DFT/TDDFT

  摘要：

  Novel tetracarbonyl complexes of type W(CO)(4)L-2 (L: 4-chlorobenzylimidazoline; 4-methylbenzylimidazoline; 3,5-dimethylbenzylimidazoline; 2,4,6-trimethylbenzylimidazoline; 2,3,5,6-tetramethylbenzylimidazoline) were synthesized. Then newly synthesized novel compounds were characterized by IR, H-1 NMR, C-13 NMR and LC-MS. The characterizations of two of the complexes have also been confirmed with single crystal X-Ray diffraction and OFT optimization results of these complexes have been compared with single crystal results. We have investigated the solvent effect on the structure and metal-to-ligand charge transfer (MLCT) transitions with OFT/TDDFT calculations with ORCA package program with BP86 functional. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2016.07.002

文献信息

• Palladium-Catalyzed Heck Reaction of Aryl Bromides in Aqueous Media Using Tris(N<i>-</i>Heterocyclic Carbene) Ligands
  作者：Ismail Özdemir、Serpil Demir、Bekir Çetinkaya

  DOI：10.1055/s-2007-973860

  日期：2007.4

  highly effective, easy to handle and environmentally benign process for palladium-mediated Heck reaction was developed. The in situ prepared three-component system composed of palladium(II) acetate, a tris(azolinium) bromide and potassium TERT-butoxide, quantitatively catalyzes the Heck reaction of aryl bromides in aqueous media.

  开发了一种高效、易于处理且环境友好的钯介导的 Heck 反应工艺。原位制备的三组分体系由乙酸钯（II）、三（唑啉）溴化物和叔丁醇钾组成，在水性介质中定量催化芳基溴化物的 Heck 反应。
• The direct C(sp2)-H functionalization and coupling of aromatic N-heterocycles with (hetero)aryl bromides by [PdX2(imidazolidin-2-ylidene)(Py)] catalysts
  作者：Murat Kaloğlu、Ichraf Slimani、Namık Özdemir、Nevin Gürbüz、Naceur Hamdi、İsmail Özdemir

  DOI：10.1016/j.jorganchem.2021.122013

  日期：2021.10

  In this study, a series of air- and moisture-stable imidazolidin-2-ylidene-based new palladium complexes with the general formula [PdX2(NHC)(Py)] were synthesized (NHC = N-heterocyclic carbene, Py = pyridine, X = Cl or I). The structures of the palladium complexes were characterized by different techniques such as 1H NMR, 13C NMR, FT-IR spectroscopy and elemental analysis. The more detailed structural

  本研究合成了一系列空气和湿气稳定的咪唑啉-2-亚基新型钯配合物，通式为[PdX 2 (NHC)(Py)]（NHC = N-杂环卡宾，Py = 吡啶, X = Cl 或 I)。钯配合物的结构通过1 H NMR、13C NMR、FT-IR光谱和元素分析。通过单晶 X 射线衍射研究确定了一种钯配合物的更详细的结构特征。所有钯配合物的催化活性在五元芳族 N-杂环如 3,5-二甲基异恶唑和 1-甲基-1H-吡咯-2-甲醛与（杂）芳基溴化物存在 1 120 °C 时的 mol% 催化剂负载量。以中等至良好的产率获得了所需的产品。
• Suzuki reaction of aryl chlorides using saturatedN-heterocarbene ligands
  作者：Ismail Özdemir、Sedat Yaşar、Serpil Demir、Bekir Çetinkaya

  DOI：10.1002/hc.20140

  日期：——

  conventional spectroscopic methods and elemental analyses. The incorporation of saturated N-heterocyclic carbenes into palladium precatalysts gives high catalyst activity in the Suzuki coupling of deactivated aryl chloride substrates in aqueous media. The complexes were generated in the presence of Pd(OAc)2 by in situ deprotonation of 2a–f. © 2005 Wiley Periodicals, Inc. Heteroatom Chem 16:557–561

  从容易获得的起始材料中，制备了六种 1,3-二烷基-咪唑啉溴化物 (2a-f)，并通过常规光谱方法和元素分析对其进行了表征。将饱和的 N-杂环卡宾掺入钯预催化剂中，在水介质中失活的芳基氯底物的 Suzuki 偶联中具有高催化剂活性。这些配合物是在 Pd(OAc)2 存在下通过 2a-f 的原位去质子化产生的。© 2005 Wiley Periodicals, Inc. 杂原子化学 16:557–561, 2005; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20140
• Imidazolinium sulfonate and sulfamate zwitterions as chiral solvating agents for enantiomeric excess calculations
  作者：Sobia Tabassum、Mazhar Amjad Gilani、René Wilhelm

  DOI：10.1016/j.tetasy.2011.09.018

  日期：2011.9

  synthesis of enantiopure unsymmetrical N-heterocyclic based zwitterions incorporating imidazolinium and alkylsulfonate or sulfamate groups is described. The desired compounds were prepared in good yields from 1,3-propanesultone or cyclic sulfamidates and imidazolines. The imidazolinium based zwitterions proved to be versatile chiral solvating agents for Mosher’s acid, alcohols, cyanohydrins, amino alcohols

  描述了结合咪唑啉鎓和烷基磺酸盐或氨基磺酸盐基团的对映体不对称基于N-杂环的两性离子的合成。由1，3-丙磺酸内酯或环状氨基磺酸酯和咪唑啉以高收率制备所需化合物。咪唑啉鎓基两性离子被证明是通用的手性溶剂化剂，用于Mosher的酸，醇，氰醇，氨基醇，硝基醇，硫醇和羧酸，在1 H和19 F NMR中具有非常高的位移。
• Benzylic Imidazolidinium, 3,4,5,6-Tetrahydropyrimidinium and Benzimidazolium Salts: Applications in Ruthenium-Catalyzed Allylic Substitution Reactions
  作者：Sedat Yasar、Ismail Özdemir、Bekir Cetinkaya、Jean-Luc Renaud、Christian Bruneau

  DOI：10.1002/ejoc.200800007

  日期：2008.4

  Imidazolidinium, tetrahydropyrimidinium and benzimidazolium salts were prepared. Upon reaction with tBuOK, they generate carbene ligands, which were associated in situ to [RuCp*(MeCN)3]PF6 to produce ruthenium catalysts that are active for the substitution of allylic substrates by dimethyl malonate as a carbonucleophile and phenol. The influences of the N-heterocyclic structures, as well as that of

  制备了咪唑啉鎓、四氢嘧啶鎓和苯并咪唑鎓盐。与 tBuOK 反应后，它们会生成卡宾配体，这些配体与 [RuCp*(MeCN)3]PF6 原位结合以产生钌催化剂，该催化剂对于丙二酸二甲酯作为亲碳试剂和苯酚取代烯丙基底物具有活性。研究了 N-杂环结构以及苄基 N-取代基对反应性和区域选择性的影响。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)