3-methyl-1-(quinolin-2-yl)-1H-imidazol-3-ium hexafluorophosphate | 1425259-93-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-methyl-1-(quinolin-2-yl)-1H-imidazol-3-ium hexafluorophosphate
• 英文别名: 2-(3-Methylimidazol-3-ium-1-yl)quinoline;hexafluorophosphate；2-(3-methylimidazol-3-ium-1-yl)quinoline;hexafluorophosphate
• CAS: 1425259-93-3
• 化学式: C₁₃H₁₂N₃*F₆P
• 分子量: 355.223
• InChiKey: XOBJIHSMTBTLQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.23
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-辛炔 、 3-methyl-1-(quinolin-2-yl)-1H-imidazol-3-ium hexafluorophosphate 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 sodium acetate 、 silver trifluoromethanesulfonate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以61%的产率得到
  参考文献：
  名称：

  Switching of “Rollover Pathway” in Rhodium(III)-Catalyzed C–H Activation of Chelating Molecules

  摘要：

  Organic molecules containing imidazolium and pyridine backbone are of special interest in many branches of chemistry, and therefore, overcoming the scarcity of their catalytic functionalization protocol leading to structurally important derivatives is strongly desired. This study demonstrates an unprecedented bimodal C-H activation functionalization catalysis on such organic molecules which contain imidazolium motif (potential N-heterocyclic carbene donor) and pyridine in chelating fashion and difficult to functionalize by trivial C-H activation strategy. The unique feature of this protocol is a flip-flop NHC-directed pyridine rollover and pyridine-directed NHC-rollover C-H activation within a stable "NHC-Rh-III-pyridine" chelate platform followed by functionalization with internal alkynes to furnish structurally important annulated products. Electronic and steric factors play a key role in achieving such novel chemistry.

  DOI：

  10.1021/acscatal.5b02540
• 作为产物：
  描述：

  2-氯喹啉 在 ammonium hexafluorophosphate 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 24.0h， 生成 3-methyl-1-(quinolin-2-yl)-1H-imidazol-3-ium hexafluorophosphate
  参考文献：
  名称：

  某些涉及N-杂环卡宾配体的银（I），金（I）和金（III）配合物的合成，结构和抗疟活性

  摘要：

  合成了一系列含有双（N-杂环卡宾）（NHC）或N-官能化的NHC配体的单核和双核银（I）和单核金（I）配合物，并通过分光光度法（在某些情况下通过单晶X射线衍射。的体外抗疟原虫和的先前所描述的家庭的抗真菌活性ñ -官能化双（咪唑）前配体和它们相应的银（I），金（I）和金（III）配合物也是新的在此描述化合物在研究耐恶性疟原虫的氯喹菌株，并针对两个假丝酵母株。对于第一个家族，发现了对双核银（I）物种有趣的抗疟原虫和抗真菌活性，但它们也显示出很强的溶血特性。导致第二系列复合物的药理调节显着提高了抗血浆活性，特别是IC 50值高达330 nM的单核金（I）复合物，而没有任何溶血作用。

  DOI：

  10.1016/j.ejmech.2012.11.038

文献信息

• Synthesis, characterization, and antileishmanial activities of gold(I) complexes involving quinoline functionalized N-heterocyclic carbenes
  作者：Lucie Paloque、Catherine Hemmert、Alexis Valentin、Heinz Gornitzka

  DOI：10.1016/j.ejmech.2015.02.046

  日期：2015.4

  neutral gold(I) complexes containing quinoline functionalized N-heterocyclic carbene(s) (NHC(s)) were synthesized and fully characterized by spectroscopic methods. The X-ray structures of two key compounds are presented. Proligands and their corresponding gold(I) complexes together with previously described silver(I) and gold(I) bis(NHC-quinoline) and gold(I) bis(NHC-methylbipyridine) complexes were evaluated

  合成了一系列新的单核阳离子或中性金（I）配合物，其中包含喹啉官能化的N-杂环卡宾（一种或多种）（NHC），并通过光谱法对其进行了全面表征。介绍了两种关键化合物的X射线结构。在体外对婴儿利什曼原虫评估了配体及其相应的金（I）配合物以及先前描述的银（I）和金（I）双（NHC-喹啉）和金（I）双（NHC-甲基联吡啶）配合物。同时，在鼠巨噬细胞J774A.1上评估了这些分子的体外细胞毒性。所有的金（I）化合物均对婴儿乳杆菌具有强效的抗疟疾活性。前鞭毛体和其中的三种还有效地对抗婴儿乳杆菌细胞内的变形虫。结构-活性和毒性之间的关系使得能够证明铅化合物（6）既显示出高活性，又显示出良好的选择性指数。
• Synthesis, structures, and antimalarial activities of some silver(I), gold(I) and gold(III) complexes involving N-heterocyclic carbene ligands
  作者：Catherine Hemmert、Aymeric Fabié、Aude Fabre、Françoise Benoit-Vical、Heinz Gornitzka

  DOI：10.1016/j.ejmech.2012.11.038

  日期：2013.2

  proligands and their corresponding silver(I), gold(I) and gold(III) complexes but also the new here described compounds were investigated in a chloroquine-resistant strain of Plasmodium falciparum, and against two Candida strains, respectively. For the first family, interesting antiplasmodial and antifungal activities were found for the dinuclear silver(I) species but they also showed strong hemolytic

  合成了一系列含有双（N-杂环卡宾）（NHC）或N-官能化的NHC配体的单核和双核银（I）和单核金（I）配合物，并通过分光光度法（在某些情况下通过单晶X射线衍射。的体外抗疟原虫和的先前所描述的家庭的抗真菌活性ñ -官能化双（咪唑）前配体和它们相应的银（I），金（I）和金（III）配合物也是新的在此描述化合物在研究耐恶性疟原虫的氯喹菌株，并针对两个假丝酵母株。对于第一个家族，发现了对双核银（I）物种有趣的抗疟原虫和抗真菌活性，但它们也显示出很强的溶血特性。导致第二系列复合物的药理调节显着提高了抗血浆活性，特别是IC 50值高达330 nM的单核金（I）复合物，而没有任何溶血作用。
• Switching of “Rollover Pathway” in Rhodium(III)-Catalyzed C–H Activation of Chelating Molecules
  作者：Debasish Ghorai、Champak Dutta、Joyanta Choudhury

  DOI：10.1021/acscatal.5b02540

  日期：2016.2.5

  Organic molecules containing imidazolium and pyridine backbone are of special interest in many branches of chemistry, and therefore, overcoming the scarcity of their catalytic functionalization protocol leading to structurally important derivatives is strongly desired. This study demonstrates an unprecedented bimodal C-H activation functionalization catalysis on such organic molecules which contain imidazolium motif (potential N-heterocyclic carbene donor) and pyridine in chelating fashion and difficult to functionalize by trivial C-H activation strategy. The unique feature of this protocol is a flip-flop NHC-directed pyridine rollover and pyridine-directed NHC-rollover C-H activation within a stable "NHC-Rh-III-pyridine" chelate platform followed by functionalization with internal alkynes to furnish structurally important annulated products. Electronic and steric factors play a key role in achieving such novel chemistry.