1,3-Bis(4,5-dihydro-1H-imidazol-2-yl)-5-tert-butylbenzene

• 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)-5-tert-butylbenzene
• 英文别名: 2,2’-(5-(tert-butyl)-1,3-phenylene)bis(4,5-dihydro-1H-imidazole)；2-(3-tert-butyl-5-(4,5-dihydro-1H-imidazol-2-yl)phenyl)-4,5-dihydro-1H-imidazole；2-[3-tert-butyl-5-(4,5-dihydro-1H-imidazol-2-yl)phenyl]-4,5-dihydro-1H-imidazole
• 化学式: C₁₆H₂₂N₄
• 分子量: 270.377
• InChiKey: DVLWKPPCFBVQLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 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)-5-tert-butylbenzene 在 甲醇 、 乙酰氯 作用下， 生成 1,3-Bis(4,5-dihydro-1H-imidazol-2-yl)-5-tert-butylbenzene dihydrochloride
  参考文献：
  名称：

  Design of a Bisamidinium Claisen Rearrangement Catalyst for Monodentate Substrates

  摘要：

  A bisamidinium catalyst has been designed for the Claisen rearrangement. The primary design feature is a dual hydrogen bonding array that can coordinate a singular oxygen atom of the substrate. The ability to function as a dual hydrogen donor is key as the bisamidinium accelerates the Claisen rearrangement to a greater extent than Bronsted acids with lower pK(a) values.

  DOI：

  10.1021/ol8026945
• 作为产物：
  描述：

  5-tert-butyl-N1,N3-bis(2-hydroxyethyl)benzene-1,3-diamide 在 氯化亚砜 、 氨 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以0.76 g的产率得到1,3-Bis(4,5-dihydro-1H-imidazol-2-yl)-5-tert-butylbenzene
  参考文献：
  名称：

  Design of a Bisamidinium Claisen Rearrangement Catalyst for Monodentate Substrates

  摘要：

  A bisamidinium catalyst has been designed for the Claisen rearrangement. The primary design feature is a dual hydrogen bonding array that can coordinate a singular oxygen atom of the substrate. The ability to function as a dual hydrogen donor is key as the bisamidinium accelerates the Claisen rearrangement to a greater extent than Bronsted acids with lower pK(a) values.

  DOI：

  10.1021/ol8026945

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。
• 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。