(4R,5R)-4,5-di-tert-butyl-2-imidazoline | 714957-95-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: (4R,5R)-4,5-di-tert-butyl-2-imidazoline
• 英文别名: (R,R)-4,5-di-tert-butylimidazoline；1H-Imidazole, 4,5-bis(1,1-dimethylethyl)-4,5-dihydro-, (4R,5R)-；(4R,5R)-4,5-ditert-butyl-4,5-dihydro-1H-imidazole
• CAS: 714957-95-6
• 化学式: C₁₁H₂₂N₂
• 分子量: 182.309
• InChiKey: VXUYNDASAUGNMM-IUCAKERBSA-N

物化性质

• 沸点：
  275.9±9.0 °C(Predicted)
• 密度：
  0.93±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4R,5R)-4,5-di-tert-butyl-2-imidazoline 在 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 63.0h， 生成 (4R,5R)-3-benzyl-4,5-di(tert-butyl)-1-(bis(2-methylphenyl)methyl)imidazolidinium chloride
  参考文献：
  名称：

  Synthesis of Chiral C 1-Symmetric N-Heterocyclic Carbene Ligands: Application toward Copper-Catalyzed Homocoupling of 2-Naphthols

  摘要：

  Novel chiral C-1-symmetric NHC ligands can be prepared via dialkylation of chiral imidazoline scaffolds. Asymmetry in the ligand/metal complexes results from a chiral relay effect. The C-1-symmetric nature of the NHC ligand was proposed to allow for improved reactivity versus other achiral and chiral NHC complexes. The benefit of such ligands was demonstrated in copper-catalyzed oxidative coupling reactions.

  DOI：

  10.1055/s-0033-1338564
• 作为产物：
  描述：

  (1R,2R)-N,N'-bis<(S)-1-phenylethyl>-1,2-di-tert-butylimidazolidine 在 palladium dihydroxide ammonium formate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以95%的产率得到(4R,5R)-4,5-di-tert-butyl-2-imidazoline
  参考文献：
  名称：

  使用手性N-杂环卡宾对映铜选择性催化1,4-共轭加成反应

  摘要：

  描述了多种手性N-杂环卡宾（NHC）前体的制备。讨论了咪唑啉鎓盐和羧甲基银作为NHC前体的相对优点，涉及它们在铜催化的将二烷基锌试剂共轭添加到多种Michael受体中时的合成，稳定性和性能。使用低至4％的手性配体即可实现高达93％的对映选择性。

  DOI：

  10.1016/j.jorganchem.2005.07.024

文献信息

• High-Throughput Screening of Metal-<i>N</i>-Heterocyclic Carbene Complexes against Biofilm Formation by Pathogenic Bacteria
  作者：Thierry Bernardi、Stéphanie Badel、Pascal Mayer、Jérome Groelly、Pierre de Frémont、Béatrice Jacques、Pierre Braunstein、Marie-Laure Teyssot、Christelle Gaulier、Federico Cisnetti、Arnaud Gautier、Sylvain Roland

  DOI：10.1002/cmdc.201402012

  日期：2014.6

  A set of molecules including a majority of metal‐N‐heterocyclic carbene (NHC) complexes (metal=Ag, Cu, and Au) and azolium salts were evaluated by high‐throughput screening of their activity against biofilm formation associated with pathogenic bacteria. The anti‐planktonic effects were compared in parallel. Representative biofilm‐forming strains of various genera were selected (Listeria, Pseudomonas

  通过高通量筛选它们对与病原菌相关的生物膜形成的活性，评估了包括大多数金属-N-杂环卡宾（NHC）配合物（金属= Ag，Cu和Au）和盐的一组分子。并行比较了抗浮游生物的作用。选择了不同属的代表性生物膜形成菌株（李斯特菌，假单胞菌，葡萄球菌和大肠埃希氏菌）。所有化合物均以1 mg L -1进行测试通过使用BioFilm环形测试。根据标准化实验值确定信息得分（IS，活性总和）和活性得分（AS，抗生物膜和抗浮游生物活性之间的差异），以根据细菌菌株对活性最高的分子进行分类。通过这种方法，我们确定了在NHC配体上具有芳族基团的亲脂性Ag I和Cu I络合物是抑制生物膜形成的最有效方法。
• Investigation of a Series of Silver-N-Heterocyclic Carbenes as Antibacterial Agents: Activity, Synergistic Effects, and Cytotoxicity
  作者：Sylvain Roland、Claude Jolivalt、Thierry Cresteil、Laure Eloy、Pascale Bouhours、Arnaud Hequet、Virginie Mansuy、Corinne Vanucci、Jean-Marc Paris

  DOI：10.1002/chem.201002812

  日期：2011.2.1

  The power of silver! Silver–N‐heterocyclic carbenes (NHCs), commonly used in catalysis, exhibit high antibacterial activity. Some are efficient at low concentrations against resistant strains of S. aureus that cause major problems to public health. Due to synergistic effects, silver–NHCs can also restore the activity of ciprofloxacin against resistant S. aureus NorA at very low concentrations (see

  银的力量！常用于催化的银-N-杂环卡宾（NHC）具有很高的抗菌活性。有些在低浓度下对抵抗金黄色葡萄球菌的耐药菌株有效，这些菌株对公共卫生造成重大问题。由于具有协同作用，银-NHC还可以在非常低的浓度下恢复环丙沙星抗金黄色葡萄球菌NorA的活性（见图）。
• Synthesis of chiral silver(I) diaminocarbene complexes from (R,R)-4,5-di-tert-butylimidazoline
  作者：Julien Pytkowicz、Sylvain Roland、Pierre Mangeney

  DOI：10.1016/s0022-328x(01)01013-0

  日期：2001.8

  A preparation of chiral silver(I) diaminocarbene complexes was developed by treatment of imidazolinium salts derived from (R,R)-4,5-di-tert-butylimidazoline with silver(I) oxide. Complexes having the chirality on the heterocycle and methyl, benzyl or picolyl groups on the nitrogen atoms have been prepared. We also performed the synthesis of diaminocarbenes having in addition the chiral (S)-1-phenylethyl moiety on the nitrogen atoms. X-ray structures of two of these carbenes (N,N ' -dimethyl and N,N ' -dibenzyl) are presented. Several methods for the preparation of imidazolinium salts are described. (C) 2001 Elsevier Science B.V. All rights reserved.
• Synthesis of Chiral C 1-Symmetric N-Heterocyclic Carbene Ligands: Application toward Copper-Catalyzed Homocoupling of 2-Naphthols
  作者：Shawn Collins、Michael Holtz-Mulholland

  DOI：10.1055/s-0033-1338564

  日期：——

  Novel chiral C-1-symmetric NHC ligands can be prepared via dialkylation of chiral imidazoline scaffolds. Asymmetry in the ligand/metal complexes results from a chiral relay effect. The C-1-symmetric nature of the NHC ligand was proposed to allow for improved reactivity versus other achiral and chiral NHC complexes. The benefit of such ligands was demonstrated in copper-catalyzed oxidative coupling reactions.
• Enantioselective copper catalysed 1,4-conjugate addition reactions using chiral N-heterocyclic carbenes
  作者：Caroline L. Winn、Frédéric Guillen、Julien Pytkowicz、Sylvain Roland、Pierre Mangeney、Alexandre Alexakis

  DOI：10.1016/j.jorganchem.2005.07.024

  日期：2005.12

  The preparation of a variety of chiral N-heterocyclic carbene (NHC) precursors is described. The relative merits of imidazolinium salts and silver carbenes as NHC precursors are discussed with respect to their synthesis, stability and performance in the copper catalysed conjugate addition of dialkyl zinc reagents to a variety of Michael acceptors. Enantioselectivities of up to 93% were achieved using

  描述了多种手性N-杂环卡宾（NHC）前体的制备。讨论了咪唑啉鎓盐和羧甲基银作为NHC前体的相对优点，涉及它们在铜催化的将二烷基锌试剂共轭添加到多种Michael受体中时的合成，稳定性和性能。使用低至4％的手性配体即可实现高达93％的对映选择性。