1,3-bis(4,5-dihydro-1H-imidazol-2-yl)benzene | 952-08-9

• 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: 1,3-bis(4,5-dihydro-1H-imidazol-2-yl)benzene
• 英文别名: 2-[3-(4,5-dihydro-1H-imidazol-2-yl)phenyl]-4,5-dihydro-1H-imidazole
• CAS: 952-08-9
• 化学式: C₁₂H₁₄N₄
• 分子量: 214.27
• InChiKey: DYVOQLHXDCWSHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  48.8
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-bis(4,5-dihydro-1H-imidazol-2-yl)benzene 在 乙酰氯 作用下， 以 甲醇 为溶剂， 反应 18.0h， 生成 1,3-Bis(4,5-dihydro-1H-imidazol-2-yl)benzene dihydrochloride
  参考文献：
  名称：

  Rapid Quantification of the Activating Effects of Hydrogen-Bonding Catalysts with a Colorimetric Sensor

  摘要：

  A sensor has been developed to quickly and simply assess the relative reactivity of different hydrogen-bonding catalysts. Specifically, blue-shifts seen upon treatment of H-bonding catalysts with the colorimetric compound 7-methyl-2-phenylimidazo[1,2-a]pyrazin-3(7H)-one correlate well to the K-eq of binding to the sensor. The blue-shifts also show a high degree of correlation with relative rates in Diels-Alder reactions of methyl vinyl ketone and cyclopentadiene employing the H-bonding catalysts. The relevance of the sensor blue-shifts to the LUMO-lowering abilities of the H-bonding catalysts is discussed.

  DOI：

  10.1021/ja3050663
• 作为产物：
  描述：

  间苯二甲腈 、 乙二胺 在 cupric indole-3-acetate 作用下， 反应 0.33h， 以89%的产率得到1,3-bis(4,5-dihydro-1H-imidazol-2-yl)benzene
  参考文献：
  名称：

  铜在不同条件下催化合成2-咪唑啉及其N-羟乙基衍生物

  摘要：

  用吲哚-3-乙酸铜（Cu）从芳族腈与乙二胺（EDA）或N-（2-氨基乙基）乙醇胺（AEEA）反应快速合成2-咪唑啉及其N-羟乙基衍生物的方法（II）–（IAA）2）作为回流和微波条件下可重复使用的催化剂的报道。并首次报道了七个新的N-羟乙基-咪唑啉。

  DOI：

  10.1016/j.tetlet.2011.01.082

文献信息

• Branched non-covalent complexes between carboxylic acids and two tris(amidines)
  作者：Arno Kraft

  DOI：10.1039/a809190k

  日期：——

  Carboxylic acids and two tris(amidine) bases formed branched 3∶1 complexes with high solubility in chlorinated and aromatic solvents, particularly when aromatic carboxylic acids with suitable solubilising substituents were used. Whereas N,N′-diethylamidine complexes 10 proved to be difficult to isolate, the respective imidazoline complexes 14 were easily purified by crystallisation. Association constants were determined for model bis(imidazoline) complexes to be about 103 dm3 mol–1 in the competitive solvent mixture CDCl3–CD3OD (97∶3).

  羧酸和两种三（脒基）碱基能形成在氯代和芳香溶剂中具有高溶解性的分支3:1复合物，特别是当使用带有合适增溶取代基的芳香羧酸时。尽管N,N'-二乙基脒复合物10难以分离，但相应的咪唑啉复合物14通过结晶容易提纯。对模型双（咪唑啉）复合物的结合常数测定在竞争性混合溶剂CDCl3-CD3OD（97:3）中的值约为103 dm3 mol-1。
• Syntheses, crystal structures and magnetic properties of three novel cobalt(ii) complexes containing imidazole derivative groups
  作者：Hong Yang、Jia-Min Chen、Jing-Jia Sun、Shi-Ping Yang、Jie Yu、Hong Tan、Wei Li

  DOI：10.1039/b808385a

  日期：——

  Three Co(II) complexes with the formulas: [Co2(Bib)3Cl2]Cl(CH3COO)}.CH3OH.H2O (1), [Co2(Bib)3Cl2]Cl2.(CH3OH)2.H2O, (2) and [Co3K1(Tib)2(CH3COO)6]PF6 (3), were obtained by self-assembly of a cobalt(II) salt with Bib and Tib (Bib = 1,3-bis(4,5-dihydro-1H-imidazol-2-yl)benzene; Tib = 1,3,5-tris(4,5-dihydro-1H-imidazol-2-yl)benzene) and were structurally and magnetically characterized. X-Ray single-crystal

  三种具有以下通式的Co（II）配合物：[Co2（Bib）3Cl2] Cl（CH3COO）}。CH3OH.H2O（1），[Co2（Bib）3Cl2] Cl2。（CH3OH）2.H2O，（2）和[Co3K1（Tib）2（CH3COO）6] PF6（3）是通过钴（II）盐与Bib和Tib（Bib = 1,3-bis（4,5-dihydro-1H -咪唑-2-基）苯； Tib ＝ 1,3,5-三（4,5-二氢-1H-咪唑-2-基）苯），并在结构和磁性上进行了表征。X射线单晶衍射表明，每个Co（II）离子均处于高度扭曲的四面体配位几何结构，与Bib配体的顺反比为1：2，在双核三螺旋中以双齿形式起作用[1]和2中的[Co2（Bib）3Cl2] 2+阳离子。在3中的[Co3K1（Tib）2（CH3COO）6]-阴离子中，每个Co（II）离子也呈高度扭曲的四面体配位几何结构，并且Tib配体在C，C，C和
• Mild, efficient, and chemoselective dehydrogenation of 2-imidazolines, bis-imidazolines, and <i>N</i>-substituted-2-imidazolines with potassium permanganate supported on montmorillonite K-10
  作者：Iraj Mohammadpoor-Baltork、Mohammad Abdollahi-Alibeik

  DOI：10.1139/v04-171

  日期：2005.2.1

  Different types of 2-imidazolines, bis-imidazolines, and N-substituted-2-imidazolines are efficiently oxidized to their corresponding imidazoles with potassium permanganate (KMnO₄) supported on montmorillonite K-10 under very mild conditions. The procedure is very simple and no strict conditions were required. Selective dehydrogenation of 2-alkyl-2-imidazolines in the presence of 2-aryl-2-imidazolines is a noteworthy advantage of this method and can be considered as a useful practical achievement in these reactions.Key words: 2-imidazolines, imidazoles, dehydrogenation, potassium permanganate, montmorillonite K-10.

  不同类型的2-咪唑啉、双咪唑啉和N-取代的2-咪唑啉可以在蒙脱石K-10载体上使用高锰酸钾(KMnO₄)在非常温和的条件下高效氧化为它们相应的咪唑化合物。该方法非常简单，无需严格条件。在2-芳基-2-咪唑啉存在时选择性脱氢2-烷基-2-咪唑啉是该方法的一个显著优势，可以被视为这些反应中的一项有用的实际成就。关键词：2-咪唑啉、咪唑化合物、脱氢、高锰酸钾、蒙脱石K-10。
• Activation of Electron-Deficient Quinones through Hydrogen-Bond-Donor-Coupled Electron Transfer
  作者：Amanda K. Turek、David J. Hardee、Andrew M. Ullman、Daniel G. Nocera、Eric N. Jacobsen

  DOI：10.1002/anie.201508060

  日期：2016.1.11

  towards electron transfer through hydrogen bonding. Whereas this effect of hydrogen bond donors (HBDs) has been observed for Lewis basic, weakly oxidizing quinones, comparable activation is not readily achieved when more reactive and synthetically useful electron‐deficient quinones are used. We have successfully employed HBD‐coupled electron transfer as a strategy to activate electron‐deficient quinones

  在各种合成和生物学环境中，醌是重要的有机氧化剂，它们很容易通过氢键活化为电子转移。尽管已经观察到路易斯碱性弱氧化醌的氢键供体（HBD）的这种作用，但是当使用反应性更强和合成上有用的缺电子醌时，很难实现可比的活化。我们已经成功地将HBD耦合电子转移作为激活缺电子醌的策略。对HBD的系统研究导致发现某些特定的HBD对电子转移的速率和热力学具有极大的影响。我们进一步证明，这些HBD可用作醌介导的模型合成转化中的催化剂。
• Efficient catalytic synthesis of 2-imidazolines and bis-imidazolines with silica supported tungstosilicic acid
  作者：Masoud Nasr-Esfahani、Morteza Montazerozohori、Majid Moghadam、Parisa Akhlaghi

  DOI：10.3998/ark.5550190.0011.207

  日期：——

  A rapid and efficient preparation of 2-imidazolines and bis-imidazolines by the reaction of ethylenediamine or 1,2-propanediamine with nitriles in the presence of catalytic amounts of tungstosilicic acid supported on SiO(2) under reflux condition, is reported. The advantages of this procedure are moderate reaction times, good to high yields and the ability to carry out the large scale reactions.

  据报道，在回流条件下，在 SiO(2) 上负载的钨硅酸催化量的存在下，乙二胺或 1,2-丙二胺与腈反应，快速有效地制备 2-咪唑啉和双咪唑啉。该方法的优点是反应时间适中、产率高到高，并且能够进行大规模反应。